18 MONTEREY COUNTY WEEKLY JUNE 11-17, 2026 www.montereycountynow.com Links—began to contest the plan, he acknowledged the frustration. “We know this transition to employees has created uncertainty and strong opinions. We respect that,” he wrote. “But I want you to understand something clearly. Every decision we make is based on the same goal: strengthening the future of caddying and creating the best environment for all caddies to succeed.” It is estimated that close to 90 percent of caddies act as independent contractors. Yet according to Golf Digest, only 9 percent of courses in the U.S. offer the service, many of these at destination clubs like Pebble Beach or at private courses. The career data firm Zippia reports there are just under 13,500 caddies, with around 3,000 of them under the Caddiemaster mantle. With no benefits available under this model, it can be a volatile career. But it’s the course they have chosen to walk. “We like the freedom,” Benson points out. Costello points to changes made based upon feedback from caddies. In response to concerns about pay, Caddiemaster added a $10 per bag service payment on top of the hourly rate. It amended the dress code to allow shorts and made scheduling concessions. Once the petition was presented, new amendments cannot be implemented by law until the NLRB vote is recorded. “Prior to the filing of the petition and any knowledge of union activity, Caddiemaster had already implemented multiple adjustments, improvements and accommodations since February,” Costello says. From the beginning, Caddiemaster promised benefits. The company now pays Social Security and Medicare, once the responsibility of the contractors—a savings of around $3,300 a year to each caddie, according to a Caddiemaster statement. It is also offering 401(k) contributions, worker’s compensation and other benefits. Such features proved important to some caddies, who warmed to the employee model. “In the beginning, I was pro-union,” Cummings says. “I don’t have health insurance. I need health insurance. I don’t have a 401(k). A 401(k) would be nice.” He currently is without health insurance, citing the cost. As one of the newer caddies, Cummings is not entrenched in the independent contractor culture. The taxes he filed quarterly as a contractor in the past added up to between $4,000-$6,000 a year. “Going from that to getting a W-2 and maybe getting some money back would be nice,” Cummings adds. “The employee model works better for me to get the full benefits.” Accepting the model has caused some backlash, Cummings notes. Most caddies predict unionization will win approval—about 90 percent signed the petition. Cummings shares their concern for the unknowns of the hourly employee model. When winter comes and available hours drop, what happens to the average pay? While uncertain as to the full ramifications of the change, Cummings was also hesitant to support unionization. “I was uncomfortable signing [the petition] just eight days after becoming an employee,” he says. He marks a division between caddies with two-decade tenure and those, like him, with 10 years or less on the bag. It’s not a solid line but, he adds, “There are a lot of caddies who agree with me. “We want better schedules. But the guys should have had patience. We should have waited three to six months.” Yet loopers agree they were blindsided by the announcement making them employees. That it was made by text without their involvement made the reaction more intense. Benson points out that such anger is still flickering. He would, he says, vote in favor of a union even if given a 10-percent raise. If the caddies unionize for collective bargaining, it may be a first in the U.S. for those at public courses. PGA Tour caddies—those who tote bags for professional golfers—organized, but they formed a nonprofit trade association for negotiating purposes rather than joining a union. Hoenes credits Caddiemaster leadership for making an effort following the initial rollout to soften the rough edges of a transition. But he remains firmly behind a collective voice in bargaining with the company. If the caddies join the union, they will be able to negotiate a new contract. “The mood is union-positive,” Benson says. “Union is about having a seat at the table.” While pay, scheduling and benefits are important aspects of the discussion leading up to June 18, it was the way the transition was announced and initially presented that sparked outrage. According to several caddies, after they were initially notified by a text message in February, there was a lull in communication before the company began hosting presentations. Pebble Beach Company CEO David Stivers has been monitoring the situation. At the start, little went smoothly. “We recognize the rollout of the new program was difficult, and there were several significant issues raised,” he said in a statement. “[Caddiemaster] knows it, takes it seriously and is working to get this right. The goal is to create a caddie program that is better for caddies and better for guests.” Pebble Beach turned to Caddiemaster 24 years ago. Scheduling up to 300 independent contractors with varied availability is a complex process and was becoming a burden. Caddiemaster—founded by a caddie— had the process down. More recently, as caddies suggest, “The mood is union-positive. Union is about having a seat at the table.” “This was a radical change,” says Tony Malokas, a veteran of 26 years on the bag. “There was only one thing we could do.”
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