Monterey, California—Last month, caddies at the iconic Pebble Beach golf course, a seaside resort that hosts annual PGA Tour events as well as periodic US Open tournaments, won a blowout union victory, becoming the first unionized caddies in the industry.

Golf caddies are an unusual group of workers. Tasked with toting players’ clubs, coaching them on making the best shots, and keeping them company as they play the course, the approximately 390 guys—they’re currently all guys—in the program cherish the freedom of their lifestyle. Long classified as independent contractors, they have enjoyed the ability to take time off or come in and pick up shifts when they please. Caddies could turn up the morning they hoped to work and receive walk-up jobs, allocated by seniority, assisting golfers who showed up without prior reservations. Many of them have been on the job for decades; the longest-tenured caddie is a veteran of almost 50 years. “Once you get a job here, you never leave,” says Justin Kipina, who after 20 years is still only #42 on the seniority list.

Pebble Beach is technically a public golf course, although its sky-high greens fees—and additional costs, including mandatory hotel stays at the resort—guarantee exclusivity. It continues to cater to Hollywood celebrities and business moguls, with an increasing number of Silicon Valley CEOs among its regulars. It’s also known as a challenging course, with winds coming in off the ocean and sloping seaside greens. Caddies are essential to the golfing experience, telling players which club to use, how to make the shot, how to avoid sending the ball over the edge of a cliff. They also tell stories, provide companionship, and even sometimes act as informal therapists for players.

Will Benson, a caddie who has been at Pebble Beach for 13 years, waxes poetic about the sport. He self-describes as “a lover, a player, a student of golf—I love the history, the theater of it, the nuance of a round of golf, the mental aspect.”

Under the independent contractor model, the caddies had essentially created an association that functioned as a quasi-union. Pebble Beach contracted with CaddieMaster, a company that manages caddie programs, to take on the day-to-day operations. (CaddieMaster is owned by Troon, the world’s largest golf hospitality management company.) Seven caddies served on the Liaison Board, which met a few times a year with management from CaddieMaster and negotiated contracts. There were some downsides to this system: The caddies knew they were up against a much more powerful corporation, and the contracts management ultimately presented to workers didn’t always match what the Liaison Board had agreed to. But ultimately workers had a form of organization and felt they were coming up with generally fair agreements. Between caddie fees and tips from clients, the caddies were making six-figure salaries while retaining control of their scheduling.

Will, who is a blues rock musician when he’s not caddying, describes the process of building relationships with repeat clients. He sends holiday texts and keeps abreast of his clients’ news mentions, messaging his congratulations on their business deals and promotions. He has developed relationships that often go far beyond the golf course. “I’ve stayed at people’s homes, their kids have stayed at my house, I’ve met their parents, they’ve seen my band play—people love and trust and respect you, and I them. There’s people that I would go to their funeral, and I hope they’d come to mine, if anything were to happen.”

Current Issue

July/August 2026 Issue

For years, the industry has treated independent contractor status for caddies as par for the course. In 2019, California legislators passed AB5, a bill primarily targeted at companies like Uber and Lyft that reclassified many independent contractors as employees under the law (Uber and Lyft refused to comply and eventually won a ballot initiative exempting gig drivers from the law). At the time, the golf industry lobbied to keep caddies excluded from the law, in an effort to preserve the system and limit their own liability; members of the Liaison Board voiced their desire to remain independent.

But the industry is changing. Notably, an influx of private equity investors have taken over many golf-related companies, including Troon. Their drive for increased profits has led to many changes, including a surprising conversion: Suddenly, Pebble Beach’s independent contractor caddies became employees. For the caddies, that meant no more liaison board and an overhaul of their negotiated system, including dramatic pay cuts and an end to their flexible scheduling.

Under the Liaison Board system, caddies turned over 13 percent of their bag fees (the price a golfer pays to have a caddie accompany them on a round) to the company and kept the rest. As management began rolling out the “phases” of their transition to an employee system, they suddenly began seizing 45–50 percent of the bag fees—while raising bag and greens fees for golfers.

With the change in the employment structure, not only did pay drop but there were also new rules for caddies to follow, a new and more rigid scheduling system, and less flexibility. Management began undermining the caddies’ seniority, scheduling them in blocks rather than allowing bidding on jobs in the old manner. Caddies who were used to receiving daily rates suddenly were switched to hourly pay. Newer caddies, whose pay rates were lower, began receiving a disproportionate share of walk-up work. Longer-term caddies had typically worked the early morning rounds. Because the golf course becomes more crowded over the course of the day, a game goes quicker at 6:30 am than at 11 am.

“You have these legendary caddies—they’ve caddied for presidents, kings, celebrities —going out in the morning and making 20 percent less than people going out at noon,” Will says. “That’s just not right. They should at least be making the same, if not more. Every caddy ever has gotten paid a daily fee.”

But management’s arrogance backfired. Employees have rights that independent contractors don’t—notably, the right to organize a union. After the caddies got e-mails and texts from management informing them that they would become employees, Justin called his colleague Mike Lehotta, a long-term member of the Liaison Board. “We knew that if we didn’t get on unionization immediately, they’d destroy the culture. It would be really, really bad not to have a voice in this process,” Justin recalled.

His next call was to the California Federation of Labor Unions, to try to find out if there was a union that would be a good fit. Meanwhile, other caddies were also researching their new options as employees. Will recalls looking up unions and filling out an online contact form. A few days later, an organizer at the Labor Federation reached out to the caddies and connected them with UNITE HERE Local 19, which already represented hospitality workers at Pebble Beach.

Meanwhile, the CEO of CaddieMaster, Dan Costello, showed up to defend the new regime. “He told me to my face, ‘Justin, the days of negotiating with caddies have ended.’”

Justin pointed out that guys were getting paid minimum wage to carry single bags. (Management raised bag fees at Pebble Beach to $175 for a single-bag carrying caddie; some of the caddies reported lower tips as clients assumed the caddies were receiving the higher amount.)

“I hear they’re hiring at McDonalds,” Costello replied. “Go put in your applications.”

By May, workers filed for a union election. “They could have avoided this whole union thing by getting six guys involved from the beginning,” Justin muses. “Greed just seeped into their souls.”

CaddieMaster has already attempted to scrape evidence of its union-busting campaign from the Web. Even the Wayback Machine only retains what looks like a beta version of CaddieMasterCares.com, complete with a washed out “Personal Letter from Dan,” a blurry graphic touting a “New Standard of Caddie Excellence,” and “Testimonials” from pro-employment caddies.

The anti-union campaign was conducted via e-mails, videos, corkboards, mailings, flyers on car windshields, and labor consultants stationed in the caddie shack, who tried to pull caddies into conversations about the union. Justin recalls seeing the caddie shack walls covered with anti-union posters.

The day before the union election, Will was working a round with another caddie when they received a text linking to a video from Dan Costello. It was a plea to vote no and give the company another chance. “Caddies are the company,” Costello emphasized, before running through the anti-worker decisions the company could have made but didn’t—and admitting to “missteps on our part” in eliminating flexible scheduling.

The anti-union materials didn’t just backfire with the caddies themselves. They also showed Pebble Beach golfers—the clients with whom caddies have built lifelong relationships—what the company was really like. Many of these golfers, themselves corporate executives, began advising the caddies on how to respond and sending e-mails to management defending the caddies. In response to the Costello video, one UK-born exec texted Will: “Holy cow. What a wanker that guy is.… No wonder you guys revolted. I’m so proud.”

The day after Costello’s plea, caddies voted to unionize by a margin of 180–56. It was a jubilant night: “The two greatest things in my life were that win, uniting the caddies, and winning best local band in Monterey,” says Will.

The caddies’ job may be unique, but their union campaign underscores a growing trend among highly specialized workers, many of whom seem like unlikely candidates for unionization, who are turning to the labor movement as means of challenging the upheaval of their workplaces and industries.

From tech workers to doctors to architects, many people are realizing that forming a union is their only chance to have a meaningful voice in the workplace and a say in any restructuring that occurs. That participation is essential, as corporations engage in mass layoffs and implement increasingly extractive policies. In the case of the Pebble Beach caddies, management at Troon and CaddieMaster perfectly illustrated the labor axiom that “the boss is the best organizer” to a tee—their greed and arrogance paved the way for workers to gain greater power in their workplace and help show others the way forward.