www.montereycountynow.com JUNE 11-17, 2026 MONTEREY COUNTY WEEKLY 17 Will Benson had spent part of the day on a flight back to Monterey. It was a Monday in February, a day after the 2026 AT&T Pebble Beach Pro-Am wrapped up— an event he often walks as a caddie for participating amateurs. This year, however, Benson decided to skip the tournament and take the opportunity to visit family in Seattle. That particular morning, his sister and niece drove him to the airport. After he landed in Monterey, Benson hopped a cab home. It was hardly a memorable return trip—until he settled in for the rest of the day. “My phone was blowing up,” Benson recalls. What happened that day led to a step unprecedented in the world of golf. On May 1, Pebble Beach caddies became hourly employees of Caddiemaster. A week later, 211 of approximately 250 caddies signed a petition asking the Florida-based company to recognize them as a union. When turned away, they filed for an election with the National Labor Relations Board. That election is set to place on Thursday, June 18. Should 50 percent plus one voter approve, caddies will become part of Unite Here Local 19, a union representing hospitality workers in the U.S. and Canada, including those at The Lodge at Pebble Beach. While some golf courses around the country hire caddies as employees, most act as independent contractors— and have for as far back as anyone can remember. In 2002, with the caddie program growing beyond its ability to manage, Pebble Beach Company turned that duty over to Caddiemaster, which began operations in 1993 and runs programs for some 70 courses nationwide. It is responsible for hiring, scheduling and all other aspects. The move toward unionization began with a text from Caddiemaster on Feb. 16 announcing the coming transition. “We felt like they dropped it on us,” says Tony Malokas, a veteran of 26 years at Pebble Beach. “We’ve all built our lives around flexibility.” Under the independent contractor format, caddies set their own schedules. Nick Galante, a 27-year Pebble Beach veteran, spent years as a professional race car driver while carrying bags. Benson, who has been on the Peninsula for 13 years after moving from Texas, played in a local band, The El Dorados. “You could work seven days a week or two days a year,” explains Jack Hoenes, a caddie for 24 years. “That’s the beauty of the job.” Hourly rates were also an initial concern. As a contractor with seniority, Hoenes made $188 per round, plus tip. The new pay structure is said to range from $16.90 to $24.98 an hour. With rounds—loops in caddying terminology—running four to five-and-a-half hours, caddies point out that it would be difficult to achieve full-time status. One caddie, who wished to remain anonymous due to fear of retribution, claims that based on workloads from 2025, only four of close to 250 caddies would have hit the 35-hours-a-week average necessary for benefits. “It was a shock,” says Jake Cummings. At 10 years in, he does not qualify for the highest rate: “When they explained about the $22.50, my heart sank.” In the weeks leading up to their first paychecks as employees rather than contractors, caddies feared reductions in pay of up to 30 percent. At the same time, Caddiemaster insisted that they would be getting a better deal. Company representatives held a series of meetings with caddies leading up to the transition, discussing benefits, scheduling, workplace expectations and compensation. But those conversations failed to assuage the anxiety. Caddiemaster CEO Dan Costello claims that with adjustments made to the initial plan, 90 percent of caddies saw gross earnings increase in the pay periods following the transition to employees on May 1. “It is important to distinguish between gross earnings and take-home pay,” he adds. “Caddies no longer have significant end-of-the-year tax payments they had to manage as independent contractors, since wages and deductions are withheld under the new program.” Costello also points to other benefits, such as overtime, paid sick leave and a monthly cell phone allowance. And several caddies admit the hit on income was not as bad as anticipated. Working two loops a day as summer approaches, Cummings says he made more this May than in past years. But many remain skeptical, especially due to the peculiarities of the occupation. Morning rounds tend to go quicker than the more crowded afternoon schedule, for one. “The pay could be the same if you work in the afternoon,” Benson says. “But there are a lot of hoops you have to jump through to make the same amount.” Recalling the meetings held before May 1, Hoenes sums up his pessimism. “After the first, I was cautiously optimistic,” he observes. “After the second, I was just cautious.” Hoenes admits the pay has been comparable to the contractor model “But we don’t want to get down the road and have it rolled back,” he adds. Unionizing, he notes, “is more for protection.” Costello emphasizes that the employee model was designed for the loopers’ benefit. In a statement posted to caddiemastercares.com, as caddies who work Pebble Beach Company’s four courses—Spyglass Hill, The Links at Spanish Bay, Del Monte Golf Course and the iconic Pebble Beach Golf After a contentious transition from contractors to employees, Pebble Beach caddies will vote on unionizing. By Dave Faries Jake Cummings, a caddie for 10 years, says that “we deserve a better hourly rate and to maintain seniority.” But he believes the benefits that come with the employee model make it worth consideration.
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