Justin Kipina is a caddie at Pebble Beach Golf Links, a position he calls “the best job in America.” He works an average of five days a week, enjoying fresh air, exercise and fellowship on one of the game’s most famous playgrounds.
The job hasn’t made him rich — at least, not by the standards of 17-Mile Drive — but it keeps him afloat in a desirable zip code and offers rewards beyond a paycheck.
“You’re spending five hours with someone on an intimate level and helping provide them with an experience of a lifetime,” Kipina said. “I don’t take it for granted for a minute how fortunate I am.”
Lately, though, Kipina’s sunny outlook has been shadowed by concern. It’s a feeling shared by many of his colleagues. Their worry stems from changes that took hold on May 1, when Caddiemaster, the company that oversees Pebble Beach’s caddie program, restructured how the operation runs.
Under the new model, the property’s 300-plus caddies shifted from independent-contractor status to employees. With that change came a move away from a flat-fee system to hourly wages ranging from $17.54 to $24.98 (excluding tips), depending on seniority and workload, along with new rules around scheduling and dress.
The goal, Caddiemaster CEO Dan Costello told GOLF.com, was improvement across the board — better compensation and working conditions for caddies; better service for guests. Early returns, he said, suggest the plan is working as intended. In the first round of payroll since the switch, the vast majority of loopers earned more than they did before, according to Caddiemaster records.
But that’s not the consensus in the caddie yard, where Kipina and three other Pebble caddies told GOLF.com the numbers compute differently.
As they tell it, the transition has resulted in reduced flexibility and smaller paychecks. Before May 1, Kipina said, he pocketed $188 from a $220 double-bag fee, not including gratuities. Under the hourly structure, he said, even a five-and-a-half-hour round at the top wage scale pays less than he previously earned.
Compounding caddie frustrations is another recent change. On May 1 — the same day the new employee model went into effect — Pebble Beach raised the fees guests pay for caddie services to $175 for a single bag and $250 for a double, up from $160 and $220, respectively. Caddies are not required at Pebble, but roughly have of guests take them. Those guests are paying more, caddies note, even as many believe the loopers are earning less.
“It’s been like a grenade going off in the caddie barn,” Kipina said. “It’s put everyone’s lives in turmoil. This isn’t just a summer gig. This is our career.”
The changes did not come without warning. Caddies got word of them in February, when Caddiemaster informed them that the longtime independent-contractor model would be replaced by the new employee structure.
Caddies may be known for keeping up and shutting up. In this case, though, they did not stay quiet.
It’s been like a grenade going off in the caddie barn. It’s put everyone’s lives in turmoil.
Pebble Beach caddie Justin Kipina
In response to their complaints, Caddiemaster made several modifications to the employee model. Among other tweaks, the company reduced weight limits on double-bag push carts, granted caddies access to the employee dining room, permitted caddies to wear shorts in any weather (previously, shorts were permitted only when temperatures exceeded 72 degrees) and added a $10-per-bag service payment.
Still, many caddies say the math no longer works in their favor.
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.”
Costello argues that those comparisons fail to capture the full picture. Independent contractors previously absorbed their own tax burdens, he said, whereas employees now receive payroll withholdings and are eligible for benefits that include healthcare eligibility and a 401(k). Gratuities, he adds, remain a significant part of the equation, and caddies retain 100 percent of those tips, which usually exceed the recommended figure of $75-per-player.
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.”
Tumult in the caddie program comes amid broader changes at Pebble Beach, where the resort has been investing heavily in upgrades, from renovations at the Lodge and the Tap Room to Gil Hanse and Jim Wagner’s ongoing redesign work at Spanish Bay.
Pebble has long made a point of taking the pulse of its guests, and for years the feedback on caddies largely has been positive, according to Pebble Beach CEO David Stivers. Even so, consistency issues surfaced often enough that the resort asked Caddiemaster to evaluate the operation.
“We don’t want guests to just have a good experience,” Stivers told GOLF.com in a phone interview. “We want them to have the best possible experience.”
Caddiemaster concluded that the employee model offered the most promising path forward. The decision, Costello said, wasn’t triggered by any single incident but by a longer-term evaluation of how to build a more sustainable program.
Founded in 1993, Caddiemaster has grown into the country’s largest caddie operator, overseeing programs at such prominent resorts and clubs as Pinehurst, Kohler and Augusta National. The company now is majority-owned by private equity.
Kipina, 48, has been collecting paychecks from Caddiemaster since 2007, when he moved from his native Michigan and started carrying bags at Pebble Beach, joining a caddie program whose roots stretch back more than a century. For most its existence, the program operated on a freelance arrangement: caddies collecting fees and tips directly from guests, with a resort caddiemaster overseeing the day-to-day. That structure remained in place until Caddiemaster took over in 2003.
There’s an irony to the company’s recent switch to an employee model. In 2020, when California’s AB5 legislation threatened to reclassify gig workers across industries — sweeping up Uber drivers, freelancers and, briefly, caddies — Caddiemaster was among the parties that successfully lobbied for an exemption to keep loopers as independent contractors. Six years later, the company opted for the employee model on its own terms.
The conflict that move stirred up now has spread beyond the caddie yard. Earlier this month, a majority of Pebble caddies petitioned to unionize. Not everyone in the caddie barn is in favor of the effort. Some loopers think those pushing for unionization moved too quickly — that they should have let the new system play out before taking a step that can’t easily be undone. Others worry about what it means to have a single union speak for a caddie yard full of wildly different personalities, circumstances and priorities.
Jake Cummings, who says he comes from a business-owning family, worries that moving to a union vote precluded Caddiemaster from making further accommodations on its own. “My thinking has been to take things day by day,” he said. “Let’s see how things play out.”
In a job that has always prized individuality, the idea of collective bargaining doesn’t sit easily with everyone. Caddiemaster, for its part, has not staked out a position on the matter.
“We respect a caddie’s right to join a union and also respect a caddie’s right not to join a union,” Costello said. “It’s their choice.”
Stiver, the Pebble CEO, said, “My only thought would be that I’d like to see them give it some time.”
As for Kipina, who supports unionization, he said he understands that caddies represent an eclectic group, and that no single resolution is apt to sit equally well with everyone. But for him, the stakes are bigger than the current dispute over hourly wages or flat fees — it’s about whether the job he cherishes will still exist for the next generation of loopers.
“That’s really what this is about,” he said. “It’s making sure people 40 or 50 years from now have the same opportunities we do now.”
The caddies’ vote is scheduled for June 18.
