The Milestone Loop

There have been some extenuating circumstances recently that have prevented me from getting to a computer. I now have a new job within the company and I feel like I’m in the middle of a whirlwind. It’s going well and I’m having fun, but it just seems like everyone is pulling me away from my computer and out of the house these days. So this post has taken me about a week to complete. I apologize for the length, because this is not a quick read. I took my time with this one because it documents a milestone in my caddying career, and I really wanted to share it with you guys. So grab a cup of coffee, some lunch, or whatever else and relax. I hope you guys enjoy it.

Okay. So I guess to start out with, I should let everyone know about a “changing of the guard” that has happened recently with the management of my company. One of the managers has not been doing his job for some time now and the owner finally stepped in and relieved him of duty. I was slated to be his replacement.

I ended up saying yes to the offer, because I’ve decided that if I’m going to be in this field for a while, I need to try and cut back a little bit on how many times a week I work as a caddie. So starting next week, I’m going to be Caddie Master-ing at 3 different clubs, 3 days a week. I get a chance to meet a crapload of people and STILL get 3-4 days a week to caddie. Plus, I finally get health benefits. So at least I don’t have to wake up in a cold sweat every night, wondering if my crack-pipe does in fact carry with it a truckload of consequences.

So that took place a couple of weeks ago. I was a little reluctant to accept the job at first, because I had such a horrendous experience in Florida being a Caddie Master and I really didn’t want to experience that again. But the other Caddie Masters firmly believed that my new experiences would be positive. I would spend the next few days trying to psyche myself up for all of the new responsibilities.

Then on Sunday I walked past the owner as he was talking to one of the senior caddies. I didn’t catch a lot of what they were saying, but I did pick up on important key phrases like: “I can’t believe we’re going to get this opportunity,” and “I wonder what the course will look like.” I just figured my boss had an opportunity to play a new golf course. I just dismissed it. Good for him.

Ten minutes later while I was unwrapping one of the healthiest-looking sausage, egg and cheese biscuits I had ever seen, the owner came into the caddie room and addressed the Caddie Master.

“Hey, make sure you know Paulie’s taking off Tuesday to be with me [the senior caddie he was speaking with earlier]. Tom, you’re coming too.”

Now I was curious. The boss-man walked out of the room. I put down my ever-so-fattening McDonalds breakfast and ran outside to see if I could catch up with him.

“Hey boss? What do you…you know…need me for on Tuesday?”

“Oh, it’s pretty cool. There’s a new Ritz-Carlton course opening up about 30 minutes from here and the owners are going to be playing it for the first time. They need some caddies sent over. I figure you, me and Paulie can take care of them. I don’t know if they’ve signed with anyone yet [a company to run their caddie program], but I might be able to use our performance as a sales-pitch.”

“Oh. Wow.”

“Yeah. Do you know where the course is?”

“Yeah, I think so.”

“Plan on being there around 7. We’ll walk the course and zap some yardages so we’re at least a little prepared for the round.”

So here we go again with another pressure loop. This time, however, the loop’s sole purpose was to help my company get another account. And as a recently promoted manager, I felt like the pressure was REALLY on to impress. To add to the stress, my boss would be caddying right alongside me. But, seeing as how he was the one who trained me to begin with, I figured that if anything bad happened, it wouldn’t be my fault. Or at least that’s how I tried to reassure myself.

On Monday, I walked into work thinking it was just going to be another normal day. Some water, a little fruit and a muffin. Then I heard something ridiculous.

“Hey Tom? Did you hear who’s teaching up at the driving range?”

“No.”

“Annika Sorenstam. Apparently she’s giving a clinic for the big Merrill Lynch group that’s going out today.”

My mouth dropped.

“You’re kidding.”

“Nope.”

“You’re fucking kidding me. She’s at the range?”

“Yeah.”

“Now?”

“Yes.”

“Holy crap.”

At that moment I realized I had to meet her. She has always been one of my idols, and I was nearly pissing myself. The Caddie Master came in on a cart.
“Hey Tom? Finish up your meal and I’ll take you over to the range as soon as you’re done.”

GREAT. AWESOME. THAT’S EXACTLY WHERE I WANTED TO GO ANYWAY.

I have never destroyed a meal so quickly in all my life. I was burping and farting as it went down. I was praying that the bathroom had some Febreeze in it so I could freshen up a bit before meeting Annika. Then again, do Swedes even shave their pits? Maybe the smell would attract her. I was torn.

So after diving into my locker to grab a bib and a towel, I raced outside to hop in the cart.

On the way over, I couldn’t stop verifying the information I had received.

“Annika is here today?”

“Yeah. I’m taking you over to the clinic now. You should be there for an hour or so.”

An hour? Oh my Lord. I’ll surely have to take a dump before then. Sorry about the smell, Annika.

“She’s really here?”

“Yes. What are you, deaf?”

I SMOKE ROCKS!

We pulled up onto the range and I saw her immediately. I couldn’t move.

“That’s really her.”

“Yeah. Her and Ian Baker-Finch are teaching the clinic. You’ll be with him today.”

“Me?”

“Yeah. Ian and Annika are going to skip around the golf course and try to play with each of the groups for at least 2-3 holes.”

I was way too over-stimulated at that moment. I needed to double-check.

“So wait. So…I’m going with one of the Merrill Lynch groups and I’m going to take care of Ian when he comes through?”

“No. You’re just with him today. Just him. Your job is to drive him around and help him make it to each group.”

“Oh. Okay.”

Nothing against Ian, but I was a little disappointed at that moment because I realized then that my chances of meeting Annika were going to be pretty slim. There was no way Ian and Annika would be with the same group on the same hole. I would have to try to find another moment to meet her. So at that point I just prayed for an opportunity.

I walked over and joined a few of the other caddies watching the clinic. This was the first chance I had to get a good long look at Annika. She was shorter than I thought she would be. Not that there’s anything wrong with that. I guess the media has just done a good job of making her larger than life. She had a very graceful way about her. Every time she spoke and gestured with her hands, it looked like she was conducting a symphony. Her voice was quiet and shy, and every time the wind kicked up we lost what she was saying. You could tell the mic-guy doing the audio for the clinic was just sweating BULLETS. I watched her hit a few drivers with that smooth, deliberate swing of hers. Just beautiful. Ian kept commenting to everyone about how much he loved her impact position, where her head was already starting to look up at the target. All three drives I witnessed were dead at her intended target with a little draw. Got me thinking about my own swing. Why oh why do I try to hit the ball so hard? Why can’t I focus more on tempo?

Then my attention turned from Annika to Ian. God he was tan. I think that’s why his eyes and teeth looked so white. And boy oh boy was Finchy a smooth operator. His knowledge of the golf swing just oozed out of his pores. The audience hung on his every word, and he finished off every sentence with an award-winning smile. As Ian and Annika started making their way over to the bunkers to finish up the clinic, the Caddie Master tapped me on the shoulder.

“I think now you should go over and clean his clubs. And don’t be surprised if he uses a rangefinder out there today. Last time I caddied for him that was all he used.”

Normally, I’d probably be a little disappointed hearing that news. I think everyone here knows how I feel about rangefinders. But hey, it’s Ian Baker-Finch. He can do whatever the hell he wants with me. Well, almost anything. I wonder if he smokes rocks.

Just as an aside—I know this is stupid, but for some reason I just couldn’t figure something out: Ian Baker-Finch. Do I call him Mr. Baker-Finch? No, that sounds weird. Do I call him Mr. Finch? No. For some reason that doesn’t sound right either. Should I call him Mr. Baker? IBF? What? I’ve never caddied for somebody with a freakin’ hyphen in their name before. Why oh why does this happen to me NOW? Why couldn’t this have happened on a day when I was caddying for some rich widow named Mrs. Golden-Trophy or something?

So I walked over and started polishing his Callaway’s. They were forged cavity-backs with steel 6.0 rifle bubble-shafts (didn’t know they made steel bubble shafts—I guess they could’ve just been fat shafts), and as I looked at some of the other clubs in his bag, I could tell he liked to keep all of his clubs in MINT condition (Although, now that I think about it, I suppose ALL pros would like their clubs kept that way). So I started scrubbing away, even making an effort to get out all of the dirt stuck inside the NUMBER on each iron. Just as I was finishing, the crowd around the bunker began to disperse and Ian started to make his way over to me. After a few handshakes and pats on the back for the participating players, we made eye contact.

“Hey, I’m Tom. I’ll be taking care of you today.”

“Oh, excellent mate. I’m Ian.”

“Nice to meet you Ian.”

Thank God. Ian. I’ll just call him Ian. He had a good firm handshake and a sincere smile to boot. He walked away for a minute or two so some of the other players could get in some last minute pictures before everyone broke away to tee off. But before long I had his bag on the back of a nearby cart and we were making our way down to the first tee.

“Any chance we could get some waters, mate? I’m sure I’ll be drinking like a fish today.”

“Yeah, it is pretty hot. No problem. I’ll be back in a minute.”

Now, I knew where every freakin’ bottle of water could be found ON the golf course, but I had no idea where any of the waters were in the clubhouse. That meant dealing with the food service staff. Great. And I’m not sure what all of you have experienced, but one thing I’ve noticed is: if you’re inside the clubhouse eating, the service is great. But as soon as you need even an ICE CUBE brought OUTSIDE the building, the service becomes snail-like. Well, here goes nothing. I found an outside staff member and asked him to radio in.

As Ian mingled with some of the more important guests, I saw a foursome materialize on the first tee. I, of course, panicked. I was sure that caddying would be a very minor part of today, and so I was still a little confused as to how I might go about “helping” Ian out there. The way I saw it, I was simply a logistics consultant, helping him get to as many of the groups as possible before all 10 of them finished 18 holes. So I found the Caddie Master and asked him if the group on the tee was where Ian should start.

“I have no idea what’s going on right now.”

Look, I know it’s a mad house around here, but I NEED you right now bud.

“Is that one of the Merrill Lynch groups on the first tee?”

“I think so.”

“You think?”

“Yeah.”

Okay. Well at least I know now that panicking isn’t out of the question. Ian glanced over at the first tee and then back at me for some kind of a sign. Should we be over there? Well, I don’t really know Mr. Ian Baker-Finch. But what the hell. Let’s take a risk.

“You ready Ian?”

“Oh yeah. Let’s go.”

Crap. Ian wanted water. Where the hell was food service? But just then the outside staff guy I had approached a moment earlier came around the corner with a cooler in his hand. I could’ve kissed him.

“Thanks so much.”
“You’re welcome. There are 6 in there. I filled it with ice because only half of them are cold.”

Perfect.

“Oh, are those the waters mate?”

“Yep, here you go Ian.”

“Great. Is that our group teeing off right now?”

“Yeah.”

“Well, let’s see if we can catch them.”

He grabbed his driver and ran over to the tee. He called out to the group, who had just finished teeing off.

“My wife’s been telling me for years I need to learn how to follow directions. Sorry I’m late.”

Good save, Ian. And that was the start of our time together. For the first few holes, I didn’t really say very much. I knew he had business to attend to, and I just wanted to be the grease that kept his whole plan in motion. He was in the business of entertaining clients. At least today. A little lesson here, some jokes there. And then there was the recurring question.

“So, Ian: if you only had a few days to live, where would you play golf?”

“You know, I’ve been hearing this a lot today. And most people have been suggesting courses like Winged Foot, Oakmont, etc. I have to say, those are all great courses, but they kick the living crap out of you. If I only had 3 days to live, why would I want to punish myself? I think I’d choose a course like Cypress Point or National Golf Club. Some place enjoyable.”

After seeing almost half of the groups, we stopped for lunch. And that’s when I saw her again: Annika. She was eating, signing autographs and trying to hold a conversation with 3 people at the same time. It was impressive to watch. I was pretty sure that if I ever tried to do something like that, a violent and gassy seizure would ensue. That’s way too much to handle at once. But she still remained very calm and collected. The caddie assigned to her for the day was standing next to me.

“So, how’s Annika? Is she great?”

“Oh, she’s fine. We’re just doing a lot of standing around today.”

Okay then. Not really the long-winded, enthusiastic answer I was looking for. But it’ll do.

I just stood and stared. Impolite? Yes. But her back was to me, and I figured hey, when will I ever get to see Annika up that close again? I wanted so badly to tap her on the shoulder and say hello, or wish her good luck, or ask her to marry me. But like I said, she had her hands full with the Merrill Lynch people and I didn’t want to interrupt them. I’m sure they paid her a huge sum of money just to show up, and I wasn’t about to take away any of their time with her. Then again, that still meant I hadn’t actually MET her yet. And as soon as I had that thought, she climbed back into her golf cart and drove away, riding off into the sunset. Which I thought was really weird because it was only 1:34 pm. But I guess it was just destiny.

At about 1:45 pm the sun came back up, yelled, “PSYCHE!” And Ian finished his lunch. It was time to get back to work.

After a while Ian started giving me free reign over his copy of the tee sheet. At the start of the round, he had the sheet in his pocket and would refer to it as he was talking to himself, deciding on his own where we should go and then telling me which hole to try. But by the time we had seen a few more groups, he handed me the sheet and gave me a chance to show him how useful I could be.

“So where are we headed now Tom?”

“Well, we have two choices: we can either play 18 again with the group who just finished 17 or jump back to 16 and spend a little more time with Mr. Smith’s group. We haven’t really seen a whole lot of them today.”

“Right. Back to 16 then.”

And after a few more quick lessons and a few more canned “I’ll see you guys inside for a nice cold one” responses, we were back in the staging area saying our goodbyes so he COULD in fact go inside for a nice cold one. Surprisingly, it was a very busy day. I really admired how well he was able to keep his cool even after all of those lessons and after all of those pictures. I mean we just FLEW around the golf course today. I think it would be impossible for anybody BUT a professional golfer to keep their head on straight and continue to hit solid golf shots during a crazy day like that. This guy certainly knows the business he’s in.

“Tom, thank you so much. Are they looking after you inside?”

Oh, yes. The tip. I had completely forgotten.

“Yes, yes they are. Please don’t worry about it.”

“Well, I had a great time. And I don’t care if they are looking after you inside or not. I want to at least make an effort to look after you. Here you go. Thanks so much for all your help. Have a cold one on me.”

I certainly will.

That was Monday. Although I didn’t know it at the time, Monday was actually the “warm-up” to the main event: Tuesday. Without exaggeration, Tuesday will probably go down in history as the greatest caddie round of my life.

At the start, Tuesday was a little crazy because I was headed to a brand new golf course and it didn’t really have an “address” per se. It was simply designated with a “star” off of a road I was only slightly familiar with. I think Captain Jack Sparrow had a better idea where he was headed as he jumped into the Leviathan’s mouth.

Amazingly, I ended up finding the golf course without a problem, but the entrance threw me for a loop. I was expecting a grand old club house and a lavish driveway, but what I didn’t realize was that the clubhouse hasn’t even been BUILT yet. It’s merely a drawing in somebody’s OFFICE at this point. So those two or three smaller white houses near the gate? Yeah. Should’ve stopped there. But no. I decided to press on and keep going.

About 10 minutes later, as I was driving around yet ANOTHER ridiculous turn DEEP into the 900 acre property, I got a phone call from Paulie.

“Tom? Where are you going? I saw you blow by the clubhouse like 10 minutes ago.”

“Oh crap. THAT’S the clubhouse? I’ll be right back.”

So I flew back down and around the course. I tell ya, if that place ever wanted to raise some money prior to the grand opening, they could always hold a rally race down these hills. Twists and turns everywhere and I could almost get up around 50 mph before I started to poop my pants. After dodging a few golf maintenance vehicles and missing a few forest creatures, I made it back to the temporary clubhouse.

Paulie had already grabbed a cart, and the Superintendent was standing by to guide us over to the first tee. The boss was running a little late, so we figured we’d go through the first few holes and then meet up with him as we made our way over to 4. I’m not sure if it was because this was a brand new course or because he was just a nice guy, but the Superintendent was fantastic. He told us a little about the history of the course, some of the tricky holes to watch out for and a general idea of how to get around. Then he just left us. I never would’ve thought he’d just trust us enough to leave us to our own devices. Then again, what could we really do to the golf course? It’s not like we had any Carl Spackler explosives handy.

The course is a Jack Nicklaus design. I’ve never seen one of his designs before, but from what I could gather from the website, the goal of the course was to try and imitate Jack’s precise nature. In other words, only careful shot-making and course management would be tolerated. And that description was exactly right. We were shooting various targets from the Championship tees (which would be playing around 7300 yards), and I tell you: you could NOT hit a drive any further than 280-290. If you did, you would run through the fairway into a hazard. Bunkers were well placed; the greens were the size of rare postage stamps and the thick rough and fescue were just unmerciful. If you didn’t hit every single one of your intended targets, you were fucked. I can’t wait to hear what the slope and rating for this course will be.

Now, from a caddies’ perspective, the course was impossible. The owners would later claim that this is a “walking course,” but I just can’t see how that would be possible when the average walk from green to tee is around 80-120 yards. For instance: the 9th green to the 10th tee? 300 yards, straight up a hill. The course was beautiful, yes, but you simply have to ride in a cart. Well, that, and snort bug spray. Those little bastards were just ITCHING to violate my tear ducts.

As we approached the 3rd hole, a cart was making its way down the fairway towards us. It was the boss. He had on his aviators (incredibly large sunglasses) and looked like he had just rolled out of bed.

“So what’s goin’ on boys?”

“This course is sick. Very beautiful, very difficult. I hope we get a chance to play it.”

“Well that’s what they were talking about over the phone. They’d love for us to come back. The even hinted that we might be able to play it today.”

Well, that did sound great, but I had a feeling we were in for a long day. There’s no way in hell I wanted to work for 6 hours and then be punished for another 3-4. But who knows. Maybe I’ll have the energy.

So there we were, Paulie at the wheel, me with a rangefinder and the boss-man shouting out targets for me to hit.

“What is it to that big tree on the left? How far is it just over the hazard? What is it to the front of that bunker?”

I was actually starting to feel a little worn out ALREADY. But I think we were getting some really valuable yardages recorded. The boss has been caddying for 18 years (not so much recently, but still) so you have to think that at least SOME of the obscure targets we were recording would come into play. I also have to say, that after seeing the golf course in its entirety, it will undoubtedly serve as a great training aid for any golfer who steps up to play it. It will force players to hit to specific spots. They have no choice. If they’re too long, their either in a bunker, a hazard, or deep rough. If they’re too short, they’re either in a bunker, a hazard, or deep rough. There are even a few holes where being on the wrong side of the fairway completely blocks you out from a decent approach shot into the green. At a quick glance, the course looks very forgiving, if only because it’s so big. But once you take note of some of the yardages, you’ll quickly realize how tight and unforgiving the course really is. My hat is off to Jack Nicklaus.

So with all of our recorded yardages in a little notebook, we made our way up to the driving range to meet two of the owners. According to the boss, today would be a fivesome: the three owners (two brothers and the father), the CEO of Ritz-Carlton, and Ian Baker-Finch. The two brothers were practicing at the range. As we pulled up, all three of us seemed to get out of the cart, take off our caps and extend our hands simultaneously.

The brothers seemed nice enough, but we quickly realized how business-oriented they were as a dump-truck pulled into the main entrance and came to rest on the cobblestone drive. The younger brother grabbed his phone and dialed a number.

“Excuse me fellahs. I can’t fucking stand this. Yes. Winston? Would you get out here please? There’s a fucking truck parked on our new driveway. I want the driver’s name, license plate, company name and a phone number. If he damaged that driveway at ALL, we are NOT paying for it.”

And, just as quickly as he had turned it on, he took a deep breath and turned his hardcore business-side back off.

“Sorry. I just can’t stand things like that.”

My boss quickly responded.

“No, I wouldn’t be able to stand it either. This is quite a facility you guys are putting together.”

“Oh yeah? Did you guys like the course?”

“Loved it.”

“Oh, and I spoke with a friend of yours yesterday. Mr. Big? You know him, right?”

My boss froze. Mr. Big was the owner of one of the largest caddie companies in the United States.

“You do realize we’re competitors, right?”

Insert awkward pause here.

“Oh, no. I’m sorry. I thought you two worked together.”

“Nope. I own a caddie company which runs 4 out of the top 6 programs around here. I’m not saying you need to do business with me, but I’d love to get a lunch with you next week.”

“Oh, yeah. No problem. I’d love to.”

“Alright. Well, we’re going to go back to the parking lot and start getting ready to caddie. We’ll be back in like 10 minutes.”

“Okay, great. Ian and Mr. Carlton should be here shortly.”

The boss perked up a bit.

“Yeah, Tom caddied for Ian yesterday.”

“Really? How did that go?”

“Great. Ian has no idea Tom’s here today.”

“Oh really? Well that’ll be a nice surprise.”

And then we took our leave. Back to the parking lot to get ready. My boss was already feeling confident.

“A meeting with one of the owners next week? Well, I already got what I wanted out of today. I think I’ll get out of here and let you two handle the fivesome.”

Pause.

“Just kidding. I know you two could handle it, but I still want to be here if these guys end up wanting to talk business with me. Although, they might not want to. It sounds like Mr. Big already has a contract started with them. This may be a lost cause.”

Just as an aside: none of us knew this at the time, but the owners of the club already had a contract from our competitors on their desk, ready to sign, THAT DAY. There was almost no chance we were going to get a contract started with these guys for the benefit of OUR Company. But again, we didn’t know this. We were just there to caddie, and to hope.

Back in the parking lot, I felt like I was getting ready for the Super Bowl. I was taking my time with the sun-block, making sure to carefully spray the brim of my cap with bug-spray, talking with Paulie about some of the yardages we recorded; I even targeted a few of the trees nearby with my rangefinder to see how fast I could get a yardage. I found out rather quickly that I wasn’t really that coordinated with it. I couldn’t seem to get the laser on my target. Whenever I tried to click the button I’d twitch, causing the laser to neuter one of the nearby squirrels. Sorry little buddy, but you’re taking one for the team today. I think the biggest problem was that I had an older rangefinder. I couldn’t just shoot the flagstick and get a yardage. I had to aim for the base of the pin and hope that I hit a yardage close to what the actual yardage was. The only problem with THAT is, if there are any crazy undulations in the green between me and the flagstick, my rangefinder becomes useless. Great. Well, even Superman had to deal with kryptonite.

After getting water for our towels, we walked back over to the range. The two brothers had just finished their warm-up routines and told us they’d be back shortly with Ian and the rest of the group. For a moment or two we just stood and stared at each other. We were all anxious to get going. None of us wanted to wait around. My boss spoke up.

“Paulie, throw me a few of those balls. I want to get a feel for how fast these greens are rolling.”

Well, at least that’s a good way to pass the time. The practice green behind us looked amazing, and so we all decided to get a feel for speed. For about 3 minutes we were all focused and zoned in on our respective lines, trying to get an idea of how a ball might react on the course. After that, however, we stopped being productive. It wasn’t long before we all started lobbing balls across the green to see if we could hole out. We ended up doing that for 20 minutes. That was a long 20 minutes. I couldn’t wait until everyone got back.

Right when I started walking back to the parking lot to grab my crack-pipe, the fivesome made their way over to the range: the two brothers, their father, Ian Baker-Finch and the CEO of Ritz-Carlton.

I froze at first. For a moment I felt as though I didn’t belong. Well, either THAT or I just felt like I was plastered right in the middle of a Dali painting. This whole thing felt way too surreal. Mr. Carlton was riding with Ian. It’s like I didn’t know what to say to them. The golfers all parked their carts and sat there staring at us for a moment. Fortunately, my boss snapped me out of it.

“Tommy, get over there and introduce yourself. Break this tension.”

“Hey Ian. What’s goin’ on?”

“Hey, I know this guy! Tom! Nice to see you.”

“You too.”

“See, NOW we get to have some fun…no more lessons or schmoozing…just golf and good company.”

“Yeah, I have to say I was impressed with how professional you were yesterday.”

“Well, that’s how you can tell you’ve found yourself in a good job. You’re willing to put in the overtime.”

And with that, he offered me his signature smile and grabbed a couple clubs to start warming up. I turned around to find that my introduction had done a world of good. Now everyone was introducing themselves. Next I approached the CEO.

“How are you? I’m Tom.”

“Tom? The name’s Carlton. Ritz-Carlton.”

“Nice to meet you Mr. Carlton.”

Weird. I wasn’t nervous anymore. I had this strange feeling wash over me, like I suddenly realized that these guys were on MY turf.

I just met the CEO of Ritz-Carlton. I was amazed at how comfortable I felt at that moment, because you could just sense how powerful the guy was. His handshake, his chiseled smile and even his glare were Hogan-esque. If you were to run into this guy on the street, you would know he was important. He seemed a little distant at first, like he really didn’t have any interest in meeting me at all. And, well, I’m sure there’s some truth to that. But honestly, that’s the way I wanted it. I wanted a challenge.

As the group started warming up, I somehow found myself around Ian and Mr. Carlton throughout the entire practice session. I looked over at Paulie, who was already joking around with the brothers, and my boss was at the far-end of the group trying to get to know the father. After cleaning a few of Mr. Carlton’s clubs, I carefully backed away from their cart and made my way over to the boss.

“So how are we doing this? Who do you want me to take?”

“I think you should go with Ian because you went with him yesterday. Paulie will take the two brothers, and I’ll take the father.”

“You okay with that?”

“Me? Oh, absolutely. I’d rather take a backseat on this loop anyway. You guys are the one’s that’ll have to impress. I’m the owner. I can’t be the one doing all the work. I want you guys running the show.”

And with that, the fivesome finished their warm-ups and walked back to the carts. After an obligatory: “Are you on, Tom?” We all made our way over to the first tee.

On the way, I noticed a rather ornate sign with the letters “CH” inscribed on the face. Ian spoke up.

“What’s that sign for? The Clubhouse?”

Well, I guess that answers that question. One of the brothers’ answered excitedly: “Yeah, and oh boy, you should see some of the drawings we have in the office for it. I’ll show them to you when we get finished.”

I started chuckling to myself. Only a private club would do something like that: stick a $700 sign in the ground just to show everyone where the new Clubhouse is going. Wouldn’t a little paint on a stick suffice? Oh well. I guess if you’re going to build a private golf course, go big.

There were 9 of us in all: 5 players, 3 caddies and a cameraman. The camera-guy brought up the rear of our little procession, and he had even strapped down a ladder to the back of his cart in case he needed to get a funky angle while we were out there. And may I just say, this guy HAD to be on something. He had a permanent joker-smile tattooed on his face and from the moment we all met him till the moment we all parted ways, he never stopped moving. As soon as we arrived at the first tee, he quickly jumped out of his cart and bounced around the group snapping pictures of our every move.

To add to the confusion, once the brakes on the carts were engaged, everyone decided to talk at once.

“See how beautiful this is Ian?”

“Is that the green up there? That puny thing?”

“Yeah, isn’t it great?”

“You should’ve seen how much earth we had to move for the left-side of the fairway.”

And as they talked, they all started to pose. It looked like an old-school Madonna video. One of the brothers would carefully place his hand on Mr. Carlton’s shoulder, they’d both gaze heroically out into the horizon and one of them would extend an arm and point, as if there was something very interesting happening out in the fairway bunker on the left. But, the more they posed, the more photos that crazy camera-guy (who was driving a Benz by the way…ahem…can anyone say: “misappropriated funds”?) fired off.

After about 5 minutes of embracing Dadaism, they all got together on the tee box for a “normal” looking shot of the group. The three of us hung back on one of the other tee-boxes and watched. Then we had an idea: why don’t we pose as well? I’m not sure if this actually made it into one of the pictures, but the three of us put our arms around each other and smiled for the camera. Because even though this was a historic day for these fellows, it was also a historic day for us. We were going to be a part of something special.

A few minutes before the first ball was in the air the group decided that they wanted to walk most of the time, and that meant the three of us would be driving the golf carts. We didn’t realize it until later, but that was quite a gift. Driving a golf cart or riding on the back of one is the ONLY way a caddie can survive a loop at this course. For lack of a better term, it was a Bear.

One of the brothers’ kicked it off. “Would you like to know where to hit it Ian?”

The round had begun.

“No.”

Oooooookay.

“It has always been a belief of mine that a good course designer shows you were to go. And as you can see, Jack has illustrated nicely that staying right is the best play.”

That comment threw us off for the first few holes. As a caddie, if you’re carrying a bag or running in front of a cart, it’s easy to show a little hustle and impress the group. But when you’re just DRIVING the golf cart? It’s hard not to look like a lazy asshole. All of the yardages we had recorded earlier gave us the credentials to offer some advice as to where a player might want to go. But now Ian put a stop to that. So regardless of how much we had tried to prepare by analyzing the course, picking out specific targets to aim for and calculating carry-yardages, we were back to simply being in the right place at the right time, yardage in hand. It might be a little difficult to actually LOOK like we were working out there.

At first it seemed like we had lost control of the group. I think as caddies we were just trying to do too much. We had never caddied together, much less under these circumstances, and it was like we couldn’t yet trust each other to do certain tasks. When I say “tasks,” I mean things like raking bunkers, getting divots, etc. We would jump on another players’ divot and replace it, even if the other caddie was just about to do the same. The term my boss uses for this is “over-caddying.” It happens when you don’t find a groove and can’t seem to get comfortable with the group. And until my bosses’ player—the father and part-owner of the golf course—skanked a few into the hazard, we were in danger of missing that all-important groove completely.

The fourth hole at this club is destined to be the number 1 handicap. It’s a long, downhill par 4 that dog-leg’s left around a pond. Even after a solid tee shot (280-300), you’re still left with 160-180 yards over a lateral hazard to a narrow green. That’s off the Championship Tees. Ian and Mr. Carlton both KILLED their tee shots and then followed them up with solid approach shots to be on the green putting for birdie. The father, however, ran into some trouble.

First he was in the pond. Then he skanked his third shot right into the fescue. My boss lost that ball. Then the father skulled his “5th” shot straight into the lateral hazard in front of the green. I had a great line on it, but the weeds surrounding the hazard were so thick that 1) it completely covered the hazard so I almost stepped onto a drop-off that would’ve meant my demise, and 2) you couldn’t even see the ground. I looked for a few minutes, then the boss came over and looked for a few minutes, and then the players tried to look. But it was no use. My boss had just lost 2 balls on one hole. He has always preached that the number one rule of caddying is to NEVER lose a players’ golf ball. I think the rulebook is out the window today, gentlemen.

But like I said before, I was grateful that the father had played the 4th so poorly, because it temporarily segregated my boss from the rest of the group. That meant me and Paulie could now completely focus our attention on our own guys and start to get into a bit of a groove.

That being said, now I had to pee. I quickly handed Ian and Mr. Carlton their driver’s and took off down the cart path. I had to find somewhere to go. That’s when I realized how well Jack had framed each hole on this golf course. There was nowhere to hide. There weren’t any trees or bushes to step behind. Those only came into play if you went into a hazard. So I pulled up along the fence on the right and decided to take the initiative. I was now the first caddie to ever take a piss on this golf course. I mean hey, if this is a day for firsts, I’m making my OWN mark on this golf course.

When I turned around, I saw my boss on the left side of the hole in the rough. I guess he had the same idea. He had parked his cart sideways and was standing behind it making his mark as well. The funny part was that he was still looking back at the tee-box, which meant he was still TECHNICALLY forecaddying. Now that is the mark of a successful owner. The ability to multi-task.

It was at this point in the round when the three of us starting working together. No more working separately or overlapping on duties. One of the brothers would launch a divot over in my direction, I’d quickly toss it back to Paulie as I was making my way over to help my players’ with yardage. While on the green, one of the owners would hand me their extra clubs, and after I had organized them for an easy hand-off, I’d give Paulie a signal and he’d start making his way over in my direction. As we crossed each other on the green, we would make an exchange and I’d grab the flag. While tending the flag, I’d remind my boss about the ball mark his player had made on the front of the green. As my boss moved to fix it, Paulie had just finished his read for one of the brothers, and I was already in position to tend the flag. Hey, it may not seem like anything special, but you have to remember that we never work together on the course, and for all of us to be that in sync and focused was quite a treat. I felt like I was in a ballet.

Paulie and I were able to score some more points with our players over the next 2-3 holes as the boss moved from a hazard, to some weeds, and then back into a hazard with the father. Again, not a great situation for the boss, but it really helped me and Paulie to focus on our players and make them feel like we could help them with anything they needed. There were even a few moments when I lost sight of my boss completely because he was down over an embankment sifting through fescue. It wasn’t until he slowly peered over the crest of the hill that I realized where he had gotten off to. And then, upon seeing that one of my players was about to hit, he quickly lowered his head back down and disappeared in the high grass. He reminded me more of a sniper than a caddie at that moment.

And before we knew it, the front nine was over with. We hopped on the carts and they drove us up that long, treacherous hill where a lunch had been prepared for the 5 of them. I’ve never seen anything like it. The tent that was set up for them was the size of a small apartment, and it came with a chef, a maitre d’ and 3 other guests to join them for lunch. They had propped up professionally-framed pictures of the golf course for browsing, and laid out a spread of gazpacho, lobster, shrimp, salad, 3 different types of wraps, potato salad, a variety of desserts and 3 or 4 other items whose purpose and origin are still a mystery to me. They also had a small bar of refreshments. It was ridiculous. The CEO sent my boss back over to the parking lot for some of the beers from his cooler. After the boss was on his way, the CEO came back and told me and Paulie that he actually wanted the ENTIRE cooler to be brought over. We were grateful for the errand, because we were both too afraid to grab something to eat unless our boss was present. When we returned, the fivesome sensed our anxiety and told us to please eat whatever we wanted. And so we just destroyed what was left. I think I had 2 wraps, lobster, a chocolate tort and some sort of avocado salad. I’ve never felt so plump. I was kicking myself as I swallowed the last few bites because I had forgotten—for those 15-20 minutes of flavorful bliss—that I still had to caddie. I started stretching and PRAYING I wouldn’t have to find a bathroom before the day was done. Meanwhile, my boss just sat in the background, unable to eat because he claimed his body wouldn’t be able to handle it. He said that if he HAD tried to eat anything, even a sunflower seed, he would’ve shit his pants.

Driving out into forecaddie position on 10, I was feeling very good about what we had accomplished so far. We had found a groove, the players were starting to rely on us more and more, and even the camera-guy was backing down because he had just about had his fill with pictures for the day. But now we had another variable thrown into the mix: unexpected delays for course critiques.

It started at lunch. I overheard one of the brothers ask Ian: “So Ian, now that we’ve finished the first 9, what do you think of the course?”

I honestly don’t remember his exact response, but it was very positive. And now that pandora’s box had been opened, the brothers’ felt more and more confident to ask Ian’s opinion about almost everything the group encountered.

“What do you think of this green?”

“Is this bunker big enough?”

“Do you like how the trees frame the fairway on this hole?”

And for a while, Ian was enjoying the enquiries because he has always wanted to get into course design. He told me that the day before.

“I just think playing golf, designing courses and having a good glass of wine with some friends would be a great life.”

Yes, that would be pretty nice. I wanted to get a little more out of him, though.

“Well, you’ve probably seen so many different golf courses by now that you have a good idea of what you really enjoy playing.”

“Oh yeah. I think designing a golf course would be a great way to express myself.”

So Ian was really getting into the whole “critique” aspect of his round. And on the 11th hole the Superintendent and a few of his assistants joined the group to hear some of these critiques and offer up some suggestions.

But prior to this spat of constructive criticism, I ran into a little bit of trouble on 11. The 11th hole on this course is a super-long par 5. I think it’s over 630 yards on the card, and it’s downhill the whole way. The drive down the cart path is even a little treacherous. I was going full speed, and at about 250 yards out, the cart path makes a short, 90-degree right-hand turn to avoid a 20 foot drop-off into some rocks. If I hadn’t hit the brakes in time, I’m sure I would’ve flown off of the embankment. I think they might need a guard-rail there.

So anyway, Mr. Carlton’s ball ends up in the weeds on the right. That’s where the boss was stationed. He finds it immediately and throws it back out into the rough. In fact, this was the beginning of a trend that carried through the rest of the round: my boss was going to make every effort to give these guys decent lies. Ian bombed his drive right down the middle, about 280 yards from the creek that guarded the front of the green.

As they pulled up, Mr. Carlton stepped out and looked to me for a sign.

“It’s just over here by the edge of the fescue.”

“I know.”

He sounded angry. Maybe I’ll steer clear of this guy for a little while. I had made a great find for him on 10, and I thought he would be in a good mood by now. But I think all of the course analysis was starting to ruin his enjoyment of the day. You could already tell his game was suffering because of it.

Ian bombed a HYBRID 250 yards right down the middle. He was in a perfect location to make birdie. But that’s precisely when my kryptonite punched me in the face.

Remember the issues I was having with my rangefinder? Well, the 11th pin was up front, sitting just BEHIND an undulation in the green. So to combat this, I decided to try and aim for a point just behind the pin. I would be estimating.

“How far we got Tom? Like 45?”

My rangefinder kept reading 62. I lowered the device slightly and looked for myself. It really did look 45. I clicked the button again. Nope. 62. Maybe I’ll just subtract a little bit so he becomes a little more comfortable with the number.

“Well, I keep getting 57 from here.”

“Really? Well…okay.”

And sure enough, he flies it right over the flag.

“Well shit. That wasn’t 57. Give me another ball.”

Then he sticks it to 3 feet.

“Yep. 45 yards. I can usually guess the yardage pretty well from this distance. You might want to check the batteries on that thing.”

“Yeah, sure.”

No, the batteries are fine. It’s just old and I’m an idiot.

So great. Now he’s a little shaky with my yardages. That’s the last thing I wanted to do today. I’ve even heard of tour caddies who have been fired for screwing up a yardage. I mean, I guess I could see why. Every missed shot costs these guys money.

On 12, which is a 430 yard par 4 straight up a hill, Ian hit his first drive in the crap on the left. We’re talking HEAVY shrubbery. But I had a good line on it. I was on the right side of the fairway, and so I bolted to try and find the ball as quickly as possible.

This is a brand new course, so I knew that regardless of what ball I found in there it would have to be Ian’s. That was the only thing I had on my side. As soon as I jumped into the weeds I realized I was in for another challenge. Thorns and blackberry bushes started tearing up my legs. But as long as my movements were quick and I kept moving, I didn’t seem to notice any pain. I got to work immediately, kicking and sweeping my feet through the greenery. I covered one of my hands with my towel so I could tear through the thorns without fear of any scratches. But after five minutes of an intense search, I still hadn’t found anything. I still hadn’t even seen the ground. That’s how thick it was.

“Tommy! Get back over here and look for my man’s ball! It’s over by this post and shouldn’t be very hard to find! I’ll take a look for you. I had a good line on it too.”

So I ran back across the fairway and started looking for another ball. As I looked down, I noticed that both of my legs were covered in blood. I took a moment to try and wash most of it off with my water bottle, so as not to make my towel look “messy.” At this point, Ian and the rest of the group had made it into the fairway and were making their way towards the carts. Ian had already played another ball just in case we weren’t able to find his first one. My boss started yelling.

“Hey, Ian? You playing a Callaway?”

“Yep.”

“Right here.”

Somehow, he had found Ian’s ball. And that was amazing to me. He would later tell me that he found it underneath the weeds I had already trampled over. He used a technique he learned while caddying at Shinnecock—just put your feet close together and shuffle around until you feel something round. It was a phenomenal find, but Ian wanted nothing to do with it.

“I’m not going to play it out of there. You can just pick that one up.”

“Oh, I figured as much. I just wanted you to respect the find.”

Ian laughed. “Yes, I certainly do.”

Then he turned to me.

“So what do we have here Tom?”

I was currently in the process of trying to use my rangefinder again. But after a couple of unsuccessful tries, I put it back into my pocket.

“Screw this. I’m finding you a sprinkler head.”

Ian started laughing again.

“What does it say over there?”

“148 center, and that is where the pin is located today.”

“Alright.”

And he sticks it to 10 feet. The Superintendent and three of his assistants were all relaxing on a bench behind the green, watching all of the approach shots. And that’s when our round got REALLY slow. On holes 12, 13 and 14 the Superintendent, the brothers and the father all bombarded Ian with questions about how each hole was laid out. At first you could tell Ian was really getting into it, but by the time we reached 14 Ian started finishing his critiques with: “You know, that’s what I think, but I’m not the designer. I wouldn’t listen to me if I were you. I’m just enjoying the golf course.”

On 15 Ian and I had a quick moment together I’ll remember for some time. Like I said, he was just being BOMBARDED with questions, and I felt bad for him. On one of the previous holes, Ian referred to a small mound in front of the green as a mistake. He felt that it wasn’t necessary. His exact words were: “Well, I don’t know what the technical term is for it. I suppose you’d call it a WART or something. But I don’t think this was meant to be here.”

So on 15, while Mr. Carlton was walking across the fairway to hit his shot and the brothers were looking for their balls in the weeds on the left, I decided to try and lighten the mood.

“So how are you doing Ian? Enjoying the course so far?”

“Oh yeah. Very nice. I just wish I could play golf and not have to think about anything else. But I’m a guest today. I need to put in my two cents when they ask for it.”

“Yeah, they’ve really done a nice job setting this up. But what the heck is with the floor of these carts? Did they armor-all this to make it look better?”

“Yeah, I think they did.”

“Well that’s smart. My feet have been slipping all day today. I can’t believe I haven’t been thrown from the cart yet.”

He started laughing. “Oh yeah?”

“Yeah. No wonder the greens look so shiny. Maybe they armor-all-ed them too. I KNOW they must’ve armor-all-ed that ‘wart’ back there for you.”

“Haha. Yeah, that was pretty crazy, right? I didn’t want to make them feel bad, but that just looked weird.”

“Well don’t worry about this green up here. When I saw it this morning, I told myself that it was the only normal-looking green on the course.”

Every other green on the course is super-small with undulations galore. This green was large and almost completely flat. It almost looked out of place.

“I think you may be right.”

Well at least now he was in a better mood. And the rest of the round went off without a hitch. We rode back up with them to the parking lot, hopped off and shook hands.

“Mr. Carlton, really a pleasure to meet you.”

“Yes, thank you Tom.”

“Ian, thanks so much. It’s been a great couple of days.”

“Yeah, mate. Are you guys leaving now?”

“Well, yeah, I guess so. Believe me, I’d love to stay and hang out with you guys, but I’m sure you have some important things to take care of.”

“Oh, okay. Well I’ll tell you what: I’m going to be announcing from the 15th hole on Saturday and Sunday of Tiger’s tournament. If you guys can make it over, just come to the tower and tell the guys at the bottom that you’re ‘Finchy’s mates.’ They’ll let you come right up. I don’t even care if I’m on the air. I want to see you guys there.”

“Wow. We’ll be there.”

Then me, Paulie and the boss walked over to the parking lot to change out of our bibs and talk about the day. Needless to say, we were all pretty amped. About 15 minutes later me and Paulie took our leave, and the boss decided he’d walk back to say thank you once again to the owners for allowing us to come. I can’t make direct quotes because I wasn’t there, but apparently the owners asked Ian and the CEO what they thought about our service, and they both agreed that we should be given a chance to run the account. And after my boss left, one of the brothers’ went into their office and tore up the contract they were about to sign with our competitors.

There are still a lot of things that need to fall into place, but I might be the next Caddie Master at this course.

I’m going to stop there, because in Microsoft Word this post is already over 22 pages and I think that’s a little excessive. But to those who have reached this point, thank you so much for reading, and I will definitely be posting again soon. This new job has just blown me away with all the new responsibilities recently and I’m still trying to ground myself. But I hope everyone is doing well.