Pay the ongoing controversy in the Pebble Beach caddy yard: ‘The numbers don’t lie’

Justin Kipina is a caddy at Pebble Beach Golf Links, a position he calls “the best job in America.” He works an average of five days a week, enjoying the fresh air, exercise and participation in one of the most popular playgrounds.
The job didn’t make him rich — at least, not by 17-Mile Drive standards — but it keeps him afloat in a desirable zip code and offers rewards beyond pay.
“You spend five hours with someone close to you and you help give them the experience of a lifetime,” said Kipina. “I don’t take for granted how lucky I am.”
Lately, though, Kipina’s sunny outlook has been marred by worry. It is a sentiment shared by many of his colleagues. Their concerns stem from changes that took place on May 1, when Caddiemaster, the company that oversees Pebble Beach’s caddy program, restructured the way the activity was conducted.
Under the new model, the area’s 300-plus caddies transitioned from independent contractors to employees. With that change came a shift from a minimum wage system to hourly wages ranging from $17.54 to $24.98 (excluding tips), depending on the size and workload, and new rules regarding scheduling and dress.
The goal, said Caddiemaster CEO Dan Costello GOLF.comimproved across the board – better compensation and working conditions for caddies; better service for guests. Early returns, he said, suggest the program is working as intended. In the first round of payouts since the change, most loopers won more than before, according to Caddiemaster records.
But that’s not the consensus in the caddy yard, where Kipina and other Pebble caddies tell. GOLF.com numbers count differently.
As they say, the change has resulted in less flexibility and smaller pay checks. Before May 1, Kipina said, he deposited $188 of the $220 in two bags, not including the loan amount. Under the hourly structure, he said, even a five-and-a-half-hour round at the top pay scale pays less than what he was earning before.
Adding to the frustration of the caddy 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 caddy 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 they probably have guests taking them. Those guests pay more, the caddy notes, as many believe the loops are less profitable.
“It was like a bomb went off in the caddy barn,” said Kipina. “It’s put everyone’s lives in trouble. This is not just a summer gig. This is our job.”
The changes did not come without warning. Caddies heard about them in February, when Caddiemaster informed them that the long-standing independent contractor model would be replaced by a new employee structure.
Caddies are known for being on and off. However, this time they were not silent.
It was like a bomb going off in the caddy barn. It put everyone’s lives in trouble.
Pebble Beach artist Justin Kipina
In response to their complaints, Caddiemaster made several changes to the worker model. Among other tweaks, the company lowered weight limits on two-bag push carts, gave caddies access to the staff dining room, allowed caddies to wear shorts in any weather (previously, shorts were only allowed when the temperature exceeded 72 degrees) and added a $10-per-bag service fee.
Still, many caddies say the odds are no longer working in their favor.
Another veteran, Mike Lehotta, said he used to shell out $132 in one bag, before getting tips. His initial single-fund payments under the new plan ranged from about $99 to $129 before fees. “You can’t tell me I’m doing more than before,” said Lehotta. “The numbers don’t lie.”
Costello says those comparisons fail to capture the full picture. Independent contractors previously shouldered their own tax burden, he said, while employees now receive payroll deductions and are eligible for benefits including health care eligibility and a 401(k). Gratuities are always an important part of the equation, he adds, and caddies keep 100 percent of those tips, often exceeding the recommended amount of $75-per-player.
According to Costello, Caddiemaster records from the first full pay cycle show total pay increases of more than 12 percent, with more than 90 percent of caddies earning more and some seeing increases of 25 percent or more.
Caddies in Lehotta’s camp scratched their heads at that statistic.
“He can use the numbers the way he wants,” said Lehotta. “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 extensive changes at Pebble Beach, where the resort has been investing heavily in upgrades, from renovations to the Lodge and Tap Room to Gil Hanse and Jim Wagner’s ongoing redesign work at Spanish Bay.
Pebble has long made a point of impressing its guests, and over the years the feedback from caddies has been positive, according to Pebble Beach CEO David Stivers. Still, consistency problems were coming up often enough that the resort asked Caddiemaster to check the performance.
“We don’t want guests to have just a good experience,” said Stivers GOLF.com in a telephone interview. “We want them to get the best possible experience.”
Caddiemaster concluded that the employee model offers the most promising way forward. The decision, Costello said, was not triggered by a single incident but a long-term assessment of how to build a sustainable system.
Founded in 1993, Caddiemaster has grown to become the nation’s largest caddy operator, overseeing programs at such prominent resorts and clubs as Pinehurst, Kohler and Augusta National. The company is now majority owned by private individuals.
Kipina, 48, has been collecting Caddiemaster checks since 2007, when he moved from his hometown of Michigan and started bagging in Pebble Beach, joining a caddy program with roots that go back more than a century. For the most part, the system operated on a standalone basis: caddies collected fees and tips from guests, with a resort caddiemaster overseeing the day-to-day. That structure remained in place until Caddiemaster took over in 2003.
There is some irony with the company’s recent shift to an employee model. In 2020, when California’s AB5 law threatened to reclassify gig workers in all industries – sweeping Uber drivers, freelancers and, briefly, caddies – Caddiemaster was among the organizations that successfully lobbied to be exempted from keeping loopers as independent contractors. Six years later, the company chose the employee model on its own terms.
The argument that broke out has now spread beyond the caddy yard. Earlier this month, most of Pebble’s caddies asked to meet. Not everyone in the caddy fold is up for the effort. Some loops think that those who want unionization have moved too quickly – that they should have let the new system play out before taking action that cannot be easily reversed. Others worry about what it means to have one union speak for a caddy court full of different people, situations and priorities.
Jake Cummings, who says he comes from a family of entrepreneurs, is concerned that the move to the union vote has prevented Caddiemaster from creating more accommodation on his own. “My idea was to take things day by day,” he said. “Let’s see how things go.”
In a profession that always values the individual, the concept of collective bargaining does not sit well with everyone. Caddiemaster, on the other hand, did not reveal his position on the matter.
“We respect a caddy’s right to join a union and we respect a caddy’s right not to join a union,” Costello said. “It’s their decision.”
Stiver, Pebble’s CEO, said, “My only thought is that I’d like to see them give it time.
Regarding Kipina, who supports the establishment of unions, he said he understands that caddies represent an eclectic group, and that no single decision can sit well with everyone. But for him, the issues are bigger than the current debate over hourly wages or fees — it’s about whether the work he values will still exist for the next generation of loopers.
“That’s what this is really about,” she said. “It’s making sure that people 40 or 50 years from now have the same opportunities that we’re using now.”
Voting for caddies is scheduled for June 18.



