Caddies vs Private Equity
Golf faces a test that is going to make a lot of golfers face some facts
One of the more uncomfortable things in golf is when politics enters the fray, and I’m going to do my very best not to do that here. Of course, our President owns and operates numerous golf courses (and I truly wish he’d focus on that instead of signing the worst foreign policy treaty in modern times after starting a completely unnecessary war to distract people from the Epstein files and oh whoops I just did what I said I wasn’t going to do) — and ANYWAY, we find ourselves with a truly interesting moment that has nothing to do with the rotting fetid apricot in Washington DC, but instead private equity and caddies at some of the most famous golf courses in America.
Not every golf course has caddies - the club I belong to, for instance does not provide caddies. Many do as a way to provide youth scholarship programs like the Evans Scholars program, Youth on Course, etc. Others do this for full caddie programs, like Pinehurst, Pebble Beach, Erin Hills, etc. These are real jobs that are often quite lucrative and can be perfect for independent minded people who love golf, like working outside and want the freedom to set their own schedule, meet new people, etc.
At courses like Bandon Dunes and Brambles, the course completely stays out of the interaction between the golfer and the caddie - the caddie fee and tip goes directly to the caddie. The course takes nothing, and is otherwise not involved aside from establishing a set caddie fee and ensuring that their caddies are high quality, etc. And they have some of the very best caddies I’ve ever had the privilege of playing with.
But, like so many industries, private equity has moved on in. PE firms have invested in a majority of Troon Golf, which in addition to running many golf courses also owns a company called Caddiemaster, which in turn now runs the caddie program at Pebble Beach. (This can get complicated quickly, but hang with me.)
Caddiemaster has initiated changes - with advance warning, of course - to the Pebble Beach properties - that have essentially turned the caddies into hourly employees, instead of independent contractors. To me, this seems insane. For one, the only true complaint I can give to a course like Pebble Beach is that the pace of play can be abhorrent. And if a caddie is getting paid by the hour, where is the incentive to go faster? To wit, here’s an on property caddie:
Another veteran caddie, Mike Lehotta, said he used to clear $132 carrying a single bag, before tips. His first single-bag payouts under the new system ranged from roughly $99 to $129 before gratuities. “You can’t tell me I’m making more than I was before,” Lehotta said. “The numbers don’t lie.”
…
According to Costello, Caddiemaster records from the first full pay cycle show overall gross pay increasing by more than 12 percent, with more than 90 percent of caddies earning more and some seeing increases of 25 percent or greater.
Caddies in Lehotta’s camp scratch their heads at that arithmetic.
“He can manipulate the numbers all he wants,” Lehotta said. “To get close to what we were making a couple of months ago, you have to put in more hours.”
Yeah, that’s not good. The caddies are voting this week to unionize, which could and will have ripple effects throughout the industry - of course, many golfers (whether they work in the PE business or not) are staunchly anti-union, because they somehow think it’s bad for business, except when it’s a policeman, or a nurse, or someone they think is a good person. I don’t know, I haven’t been given the talking points.
What I do know is that the folks trying to talk the caddies out of voting in their own self-interest sound exactly as dumb as that sentence I just wrote. Here’s a good Instagram Reel on it.
Here’s another, by a phenomenal caddie Taylor who I know is moving up to Bandon Dunes and has a podcast and Substack called “Between Two Shots” you should subscribe to - he’s way smarter about this stuff than I am.
ALL of this is to say that one of the coolest part of golf, to me, is that in a sport that is so completely overrun by the wealthiest, most elite part of our society, there is a welcoming spot for people of all socioeconomic means to find a way in, to make a living, get a foot in the door - whether it’s to get help towards college or to make a career, whatever it is, this is a way you can be in golf without having the right family name, the right degree from the right school, etc., etc., etc.
And yet, like so many other parts of life, someone is trying to ruin it all because they are trying to make just a little more money. This isn’t about trying to invest more and build a better product. It’s trying to extract as much value out of something for as little as possible. That’s the private equity model.* Isn’t it okay to NOT make every last penny that you can? Isn’t it okay to leave a little money on the table for someone else? And if it’s NOT okay … why isn’t it?
*(To all of my friends who work in PE - some of them who are incredibly close friends, please know that I love you. But at least to some degree, you and the people you work with? You’re the devil. LOVE YOU.)
I’m neither smart enough or inclined to make this entire post about why private equity in particular is overreaching - there are plenty of industries where what they are doing makes sense and there are tons of inefficiencies that can be mitigated through their strategies. But this? This is not only not one of them, it’s just stupid and mean.
I’m glad caddies are fighting back and I hope that the Caddiemaster program plays ball and pays a fair wage to the caddies those excellent courses merit. Because if not, and those courses still want to charge those obscene greens fees and then offer up bad caddies? That’s REALLY not going to go well.
And honestly? That’s the free market in action
UPDATE: The votes are in … and the caddies have voted to unionize. Well, how about that? This is going to get very, very interesting.
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Thank you for writing this one Greebs!
Caddies at Pebble Beach Resorts voted decisively, 182 to 56, to have a seat at the table and negotiate face-to-face with their new corporate overlords.
Caddies were notified by text messages (text messages, not face to face, or in person, or man to man, but via TEXT!) sent the evening of February 16, informing them of the end of their freedom and the start of a corporation reaching into their wallets and taking financial choices away from them. This, mere weeks after Independent Contractor agreements were negotiated for 2026.
Caddies perceived this as an unnecessarily disrespectful insult to their good-faith bargaining at the end of 2025. The caddies were completely blindsided by what was obviously being planned even as those negations were taking place. To say caddies were skeptical of Troon/CME's definition of "good faith" or "caring" about them would be an understatement.
Caddying is not only a strenuous job, but an intensely personal one: imagine going on a blind date with two people every day, and part of your income depends on your "dates" having a great time, no matter the weather or course conditions, or their player's ratio of ego to ability. At a Resort like this, a guest interacts with many employees, reservations, front desk, bellmen, housekeepers, concierge, shuttle drivers, range assistants, pro shop staff, waiters, busboys, golf services professionals, marshalls, etc., but those are typically a couple minutes here or there. Not one of the above spends over 4 hours at a time, minimum, assisting and entertaining guests at these Resorts. Caddies do. Every day. It's a lot, and most that have not spent years caddying in this environment can imagine the demands these individuals willingly and joyously face every day. It's not for everyone, but those who love it and do it well deserve fair treatment, respect, and a decent wage.
Caddie fees charged to guests at Pebble Beach Resorts in December were $210 for double-bag service, where a man carries two golf bags over 6 miles, ideally in under 5 hours, on difficult, national-championship level courses, while providing expert advice, regardless of weather conditions and player ability. That fee went to $220 on January 1st.
Then, effective May 1st, Pebble Beach Resorts raised that fee to $250, a 19% increase in four months, thanks to CaddieMaster and Troon.
At the negotiating table in December, the Caddie Liaison Board sought a simple, good-faith rate of $200+gratuity to all caddies regardless of seniority (we all do the same strenuous job, after all) for a double or a forecaddie loop (where a caddie doesn't carry bags for two, but hustles around all over the course, finding and getting yardages for FOUR golfers), and $150 for a high-interaction, personal, single-bag job, just like you see the Tour pros getting on TV. These flat fees would've made it possible for CaddieMaster to also charge Pebble's guests a flat, transparent "referral fee" of whatever they want, relieving Pebble Beach Resort staff from being put in the awkward position of being completely unable to answer a guest who asks "How much of the fee does my caddie get?" or "How much is the Referral Fee?". No one at Pebble Beach Resorts can honestly tell a guest how much either party receives.
A senior caddie was paid $188 for a double on April 30, while Caddiemaster collected the balance of the $220 fee, $32. It just so happened that May 1 was a Friday and the last day of a CaddieMaster pay period, so the same caddie worked a double on May 1, so his first "employee" check would have exactly one loop on it.
Pebble Beach collected $250 from the guest. The caddie was paid $163. My math says the caddie's income went down, while $87 (!) went to CaddieMaster. Dan Costello, CEO of CaddieMaster, thinks his company should be praised for confiscating money that caddie earned and sending it to the feds for him. Most caddies prefer to handle the timing and amounts they send to the IRS themselves. They're professionals, after all, and paying taxes are their responsibility. Taking money out their weekly income to send to the government seriously affected many families weekly budgets and cash flow.
So Pebble charges an extra $40 for Troon, the caddie takes home less, and the IRS gets the interest-free use of whatever CaddieMaster isn't keeping for itself. No wonder caddies are hurt and fighting back.
This all could've been avoided had CaddieMaster and Pebble Beach Resorts respected these men and the sweat and dedication they put in to make sure guests paying $695 have the best experience possible, but the caddies were dismissed and ignored.
Requests to have a dialogue with Pebble Beach Resorts executives were similarly rejected.
Good faith? Respect? "Caring" is what Troon's people call this treatment of the men who do the actual work . . .
113 caddies at Pebble Beach Resorts have over 15 years of full-time service; if you roll that back to 10 years, it's 171 men. Men that have built lives around the freedom that caddying USED TO offer.
Sure, taxes, health insurance, even the bibs they had to wear, were costs they had to manage, but those were legitimate business expenses they managed for themselves.
Troon and CaddieMaster chose this.
Instead of dialogue, negotiation, and compromise, Troon/CaddieMaster showed caddies around the nation who and what they are and how they view their "employees".
182 men have taken a stand for every caddie grinding out a living in the United States.
All they're asking for is simple respect.
It remains to be seen if CaddieMaster, Troon, and Pebble Beach Resorts can rise to that seemingly low bar.
Time will tell.