Our most recent post (Caddie Talk from Pinehurst Resort and Country Club, Pinehurst, NC ), introduced Rob Custer and Jeff Clay; professional caddies at Pinehurst Resort and Country Club (“PRCC”). Our next three posts will share the details from our conversation on April 3rd, 2025 at Maxie’s Grill and Taproom.
Pinehurst, founded in 1895, is known as the birthplace/cradle of American golf. PRCC, which includes courses #1 – #10, is owned and operated by the Dedman family. Course #2 is an anchor site for future US Open’s, with dates secured in 2029, 2035, 2041 and 2047. Course #10 opened in 2024 and course #11 is currently being developed by the architectural firm Coore and Crenshaw, Inc.
Let’s begin.
What are your backgrounds; how did you land in Pinehurst?
Rob: I was in the Navy for twenty-three years as a cryptologist (intelligence). Once my daughter (Aleigh) went off to college, I moved from Williamsburg, VA to Melbourne, FL, where I met my wife (Kelly). I called a local course with a caddie program (Red Stick). They asked me a few basic questions over the phone. The phone call was followed by an interview. I found myself working as a caddie for the first time a few days later. Having caddied through the winter months, a good friend (Keith Silva) convinced me, and then Kelly, to move to Pinehurst and caddy at PRCC. I have been caddying at PRCC for the past three and a half years. I absolutely love it! The environment at PRCC is breathtaking.
Jeff: My history is a bit simpler. I was a salesman in the industrial, medical and specialty gas business, based out of our corporate headquarters in Philadelphia, until it was time to move to Pinehurst in 2005. I started caddying at PRCC in July of 2018. I have been in and around golf since I was five. I caddied as a kid growing up in Cincinnati.
What does it take to be a caddy at PRCC. What is the process?
Jeff: If you can’t tell the Caddie Master the difference between a putter and a driver, you probably won’t make it through the phone interview.
You need a degree of golf acumen. Once you pass the phone interview, then there is a face-to-face interview with a written application, followed by a five-day training class which includes orientation, forecaddie day of training, a single bag day of training and a double bag training day. If you pass those bench marks, you are given a green light and you are good to go.
Rob: I had a bit of an in, as I had previous experience at a high-end club in Florida (Red Stick). At PRCC, they conduct a phone interview; asking basic questions such as:
- How many clubs are allowed in a bag?
- How many holes on a course, etc.?
The phone interview is followed by a face-to-face interview, followed by basic training. You don’t need to be associated with golf your entire life however it is helpful to have some experience.
At what point does the Caddie Master have enough confidence to send a new caddie out on #2, #4 or #10; where a customer may be paying a $450 greens fee and a caddie fee?
Jeff: The following Monday! You are thrown to the wolves immediately.
Rob: The Caddie Master will match a green horn, carrying a single bag, with an experienced caddie.
Jeff: Experienced caddies become on-course mentors. I will tell a new caddie, up front, please ask if you are uncomfortable with a read. I will help you out, I will never embarrass you, I will never offend you. I will ask you what you think, I will join in and share my thoughts and we will go from there. At that point there is an increased level of interaction as the new caddie is not afraid to ask questions because he knows I am on his team.
Rob: The Caddie Masters know how to match the experienced caddies with the inexperienced caddies. Some caddies are not interested in mentoring new caddies because it takes away from the attention they could be providing their players. They are interested in maximizing their income.
Jeff: There is a teamwork aspect to caddying. I encourage new caddies to be team players on the course. The better connected we are through the round, the better we look to our customers.
How are you assigned?. My approach as a youngster was to stand at attention, barely leaning on the Rail, attempting to make eye contact with our incredibly intimidating Assistant Caddie Master (Frank). As I recall, the tops of Frank’s shoes were cut out due to a significant “corn” problem. Time was/time is money!
Jeff: There is absolutely no seniority at Pinehurst. Recently, Travis Kelce and Patrick Mahomes spent a few days in Pinehurst. Caddies were arbitrarily assigned.
Rob: Caddies who volunteer for 36-holes-a-day receive priority over the balance of the caddies. 36-hole caddies are followed by full-time caddies and then part-time caddies. During the season, full-time caddies are working seven-days a week with the exception of requested vacation days.
Jeff: A twenty-two-year veteran could be assigned a single bag and a caddie who has been at PRCC two weeks could be assigned double bags.
Rob: We receive a schedule on Friday for the following week with designated report times. These times are not specific tee times; they are a three-hour window. Tee times are confirmed the night before.
Jeff: With our new ClubUp app, which started last fall, we receive a starting time, a specific course and players names the night before. So, it all nets out to less than a twenty-four-hour notice.
Rob: If you want to plan ahead and take your dog to the veterinarian, it’s a real challenge because we don’t know our exact tee time until the night before.
Do you work seven days a week during the peak season?
Rob: The average full-time caddie is available seven-days-a-week however you might only get four-five days of work as the season slows down. Jeff loves to work and goes out of his way to find a loop every day. I am the guy ducking in the corner, praying “not” to get a loop so I can go hang out with my dogs or sneak in a round of golf!
What about the winter months?
Rob: I sit home and get fat because PRCC goes from a high of 220 caddies during the peak season to 80 caddies during the winter months.
Jeff: December 1st every year, our full-time staff is reduced from approximately 220 caddies to roughly 80 caddies. 80 caddies are then reduced to roughly 45 caddies between January 1st through the end of February.
At the end of February, the December caddies are asked to return, then in mid-March, all caddies are requested to return.
Rob: The actual date this year was March 11th. Caddies need to budget appropriately for the winter layoff. It’s truly feast or famine. We make a lot of money between March 15th and May 1st; it slows down a bit over the summer months and then you make a whole lot of money between August 15th and November 15th.
Jeff: The winter crew is chosen by seniority and performance.
If you are working the winter crew and the forecast calls for 34 degrees and rain, can you decide to pass on your assignment?
Jeff: No, not really, unless you take a vacation day. You are on-duty.
Are you self-employed or an employee of PRCC and how are you compensated?
Jeff: We are employed by Troon Golf, not PRCC. The player pays $80/bag for a caddie, which is divvied up between Troon Golf, PRCC and the caddie. In addition, there is a recommended $60/bag gratuity that is paid directly to the caddie.
Please share any additional information on the gratuity.
Jeff: Here at PRCC, there is a minimum ($60-/bag) recommended gratuity the player knows about prior to the round. Over my eight years, I have been given less than the minimum gratuity a handful of times. Rarely do I receive the minimum.
Rob: There is a seasonal relationship to the amount of the gratuity. In spring, when players are awakening from hibernation and on vacation with their buddies, the wallets are wide open. Our summer clientele is more local/day trippers (i.e. Charlotte) and a bit more conservative. Then, there is the fall, when the private jets start to roll in all day long. These guys, are throwing around money.
Jeff: We found out recently during our Annual Caddie Meeting that PRCC caddies worked 64,000- rounds in 2024; which set a record. In 2025, PRCC is projecting 80,000- caddie rounds. The demand for caddies at PRCC is extremely high.
Rob: Course #10, which opened on April 3rd, 2024, was ranked as the #1 new public golf course in the country. The recognition brought a tremendous amount of attention to the property as well as to PRCC. Course #10 is truly different than any other course in this town or in this area. It is absolutely beautiful!
Note: Players are not required to take a caddie. They can take a cart on course #2/course #4 (cart path only), they can push a trolly (without a caddie), or they can carry their bag. Carts are not permitted on course #10.
Do you work on all ten PRCC courses?
Jeff: 95% of caddie rounds are on #2, #4 and #10; which opened in 2024. We go where we are assigned.
Rob: I have spent a lot more time on #10 this year as compared to the other two courses.
Do caddies have a course preference?
Rob: A lot do. Some prefer #2 because they know the course really well and it is an easier walk. As stated previously; #10 is absolutely beautiful, wide open with vistas all day long, but a far more challenging walk. I am not as familiar with the greens on #10, so it is a bit more of a grind than on #2 or #4.
Jeff: Some prefer #10 as it is a satellite course and away from the main shop where five courses (#1 – #5) originate. Our rounds are shorter on #10 as compared to #2 and #4; closer to 4 ½ hours than 5 hours.
Next up, Caddie Talk (Part 3).
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