Justin Kipina is a caddy at Pebble Beach Golf Linksa position he calls “the best job in America.” He works an average of five days a week, enjoying fresh air, exercise and company in one of the game’s most famous playgrounds.
The job hasn’t made him rich—at least, not by his standards 17-mile drive — but keeps it afloat in a desirable zip code and offers rewards beyond a paycheck.
“You’re spending five hours with someone on an intimate level and you’re helping to give them an experience of a lifetime,” Kipina said. “I don’t take for granted for one minute how lucky I am.”
Recently, however, Kipina’s sunny outlook has been overshadowed by worry. It’s a sentiment shared by many of his colleagues. Their concern stems from changes that took place on May 1, when Caddiemaster, the company that oversees Pebble Beach’s caddy program, restructured the way the operation works.
Under the new model, more than 300 property bodies moved from independent contractor status to employee status. With the change came a move away from a flat-rate system to hourly wages ranging from $17.54 to $24.98 (excluding tips), depending on seniority and workload, along with new rules about scheduling and dress.
The goal, said Caddiemaster CEO Dan Costello GOLF.comit was improvement across the board – better compensation and working conditions for employees; better guest service. Early returns, he said, suggest the plan is working as intended. In the first round of payrolls since the switch, the vast majority of loopers earned more than before, according to Caddiemaster data.
But that’s not the consensus in the box yard, where Kipina and three other Pebble corpses said GOLF.com the numbers are calculated differently.
As they say, the transition has resulted in reduced flexibility and smaller payments. Before May 1, Kipina said, he received $188 out of a $220 fee for two bags, not including gratuities. Under the hourly structure, he said, even a five-and-a-half-hour shift at the top pay grade pays less than he used to earn.
Compounding caddy 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 box services to $175 for a single bag and $250 for a double, up from $160 and $220, respectively. Boxes are not required at Pebble, but roughly half of guests receive them. These guests are paying more, caddies note, even as many believe loopers are earning less.
“It’s been like a grenade going off in the morgue,” Kipina said. “This has thrown everyone’s lives into turmoil. This is not just a summer gig. This is our career.”
The changes did not come without warning. Caddies got their say in February, when Caddiemaster informed them that the long-standing independent contractor model would be replaced by the new employee structure.
Caddies can be notorious for holding and gagging. But in this case they were not silent.
It was like a grenade exploding in the corpse barn. It has thrown everyone’s lives into turmoil.
Caddy Pebble Beach Justin Kipina
In response to their complaints, Caddiemaster made some modifications to the employee model. Among other changes, the company lowered weight limits on two-bag carts, gave carts access to the employee dining room, allowed carts to wear shorts in all weathers (previously, shorts were only allowed when temperatures exceeded 72 degrees) and added a $10 service charge per bag.
However, many corpses say the math no longer works in their favor.
Another veteran caddy, Mike Lehotta, said he clears $132 carrying a single bag, before tips. His first single-bag payouts under the new system ranged from roughly $99 to $129 before bonuses. “You can’t tell me I’m doing more than before,” Lehotta said. “The numbers don’t lie.”
Costello argues that these comparisons fail to capture the full picture. Independent contractors previously absorbed their tax burden, he said, while employees now get to keep the payroll and are eligible for benefits that include health care eligibility and a 401(k). Rewards, he adds, remain an important part of the equation, and boxes keep 100 percent of those tips, which typically exceed the recommended $75 per player figure.
According to Costello, Caddiemaster data from the first full pay cycle shows that overall gross pay has increased by more than 12 percent, with more than 90 percent of employees earning more and some seeing increases of 25 percent or more.
Caddies in Lehotta’s camp scratch their heads at that arithmetic.
“He can manipulate the numbers as much as he wants,” Lehotta said. “To get close to what we were doing a few months ago, you have to put in more hours.”
The upheaval in the caddy program comes amid broader changes at Pebble Beach, where the resort has invested heavily in improvements, from renovations to the Lodge and the Tap Room to Gil Hanse and Jim Wagner. ongoing redesign work in Spanish Bay.
Pebble has long aimed to take the pulse of its guests, and for years, feedback on the boxes has been largely positive, according to Pebble Beach CEO David Stivers. However, consistency issues came up so often that the resort asked the Caddiemaster to evaluate the operation.
“We don’t want guests to just have a good experience,” Stivers said GOLF.com in a telephone 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, was not prompted by any single incident, but by a long-term assessment of how to build a more sustainable program.
Founded in 1993, Caddiemaster has grown into the nation’s largest caddy operator, overseeing programs at prominent resorts and clubs such as Pinehurst, Kohler and Augusta National. The company is now majority owned by private equity.
Kipina, 48, has been collecting Caddiemaster fees since 2007, when he moved from his native Michigan and started bagging at Pebble Beach, joining a caddy program whose roots stretch back more than a century. For most of its existence, the program operated on a stand-alone arrangement: corpses collect fees and tips directly from guests, with a tour guide overseeing each day. This structure remained in place until Caddiemaster took over in 2003.
There is an irony to the company’s recent shift to an employee model. In 2020, when California’s AB5 legislation threatened to reclassify gig workers across industries — including Uber drivers, freelancers and, briefly, caddies — Caddiemaster was among the parties that successfully lobbied for an exemption to retain loopers as independent contractors. Six years later, the company chose the employee model on its own terms.
The conflict that broke out has now spread beyond the cadio’s court. Earlier this month, most Pebble corpses asked to join. Not everyone at the box barn is in favor of the effort. Some pollsters think those pushing for unionization moved too quickly — that they should have let the new system work before taking a step that cannot be easily undone. Others worry about what it means to have a single union speak for a court filled with wildly different personalities, circumstances and priorities.
Jake Cummings, who says he comes from a business-owning family, worries the move to a union vote prevented Caddiemaster from making further accommodations himself. “My mindset has been to take things day by day,” he said. “Let’s see how things go.”
In a job that has always valued individuality, the idea of collective bargaining is not easy for everyone. Caddiemaster, for its part, has not taken a position on the matter.
“We respect a caddy’s right to join a union and we also respect a caddy’s right not to join a union,” Costello said. “It’s their choice.”
Stiver, Pebble’s CEO, said: “My only thought would be that I would 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 will sit well with everyone. But for him, the stakes are bigger than the current dispute over hourly wages or flat rates — it’s about whether the job he’s doing will continue to exist for the next generation of job seekers.
“That’s really what it’s all about,” he said. “It’s making sure that people in 40 or 50 years have the same opportunities that we have now.”
The voting of the corpses is scheduled for June 18.
