ELMSFORD, N.Y. (October 14, 2025) – Former MGACSF Caddie Scholar Oliver Wolland continues to caddie at Hudson National Golf Club on top of his duties as a member of the championships staff at the Metropolitan Golf Association.

Oliver has been caddieing at Hudson since 2019 and working at the club since 2017. At the MGA, Oliver currently serves as a championships coordinator, having previously worked as a USGA PJ Boatright intern from 2024 to 2025, also with the MGA. 

Editor's Note: Oliver's answers have been edited for length and clarity.

MGACSF: How did you first get introduced to caddieing?

Oliver: I used to work at Hudson National as a bag room attendant, helped with carts, and was a range attendant, and I'd see all the caddies walking in all the time and talk to them and find out about how cool it is to work on the course and directly with the players, and I fell in love with it.

MGACSF: How did you get connected with Hudson National?

Oliver: I saw there was a job opening to work in the kitchen, and when I interviewed for the job, they asked if I wanted to work in the golf department. I said, Yes, I'd rather work in the golf department.

MGACSF: When did you start there?

Oliver: 2017. I just turned 16, in the summer between sophomore and junior year of high school.

MGACSF: How often do you get back caddieing at Hudson National?

Oliver: I would say I do two to three rounds a week. I try to do as many as I possibly can during the busy season to keep working.

MGACSF: Did you always intend to work in the golf industry?

Oliver: It was my initial intention. I attended Coastal Carolina University for a semester out of high school and was part of the PGM program. I didn't like the school or the program as much as I thought I would. I ended up transferring to Oswego to play more competitive golf. And I love that a lot more.

MGACSF: Did you play college golf?

Oliver: Yeah, I played at Oswego State in Upstate New York.

MGACSF: What made you pursue your current position?

Oliver: I initially had a job in finance after graduating. And I really didn't like it. I was talking to my parents, and they said, 'You should do something now that you're going to love.' I visited the USGA, PGA, and MGA websites and found a job opening for the Boatright Internship, applied, and landed the position. I'm thrilled where I am.

MGACSF: How does caddieing help you with your current job?

Oliver: I would say the etiquette of being on courses all the time. I know how to act, I know how not to act. I know what to say to people and players on the course. I know how to act in the clubhouse, what to do, and what not to do, and I think it translates perfectly into this job.

MGACSF: Do you envision golf staying a part of your professional life now?

Oliver: Yeah, for as long as I can keep it. I'm happy with what I'm doing, and I see significant growth potential here. It's an excellent experience and I think it'll help in the long term.

MGACSF: How would you explain your job to somebody who doesn't necessarily work in golf, or is just a casual golfer?

Oliver: I am part of a team that runs high-level local tournaments. I assist with the behind-the-scenes operations of running these professional and amateur events, where talented golfers compete.

MGACSF: How did the Caddie Scholarship Fund help you in college?

Oliver: It allowed me to go through college with minimal debt. I received a very generous scholarship, which allowed me not to worry about paying off debt after graduation. I had the opportunity to attend college, play golf, enjoy it, and then find a job, start saving, and do real adult things.

MGACSF: How did the support of the CSF help or impact you while you were in college?

Oliver: I would say it helped me. It gave me a little extra drive to do my work. I had to maintain a certain GPA. Although I believe I exceeded it in most semesters. In the back of my mind, I knew I had to work hard to keep the scholarship because it's a privilege. I needed to earn it.

MGACSF: What would you say to your younger self or kids in high school right now about caddieing or working at a country club, and how it can be a benefit to you?

Oliver: I would say that if you go into it only worrying about the cash that you get handed after the round, you're not going to like it as much as if you really try to connect with the players. I think it's as much about networking as it is a job. These people do quite well for themselves, and they really do want to help you out if they see that you are invested in your job. Talk to them about life and their experiences, listen, and learn the game because golf is a lifelong sport. So you want to be as, uh, you know, in tune with the game as you can be throughout, you know, your time caddieing

MGACSF: Five years ago, would you have envisioned yourself being where you are?

Oliver: Probably not because I had just left the PGM program. But I'm happy with how it turned out. I believe I made many of the right moves in the past five years to get to where I am, and I couldn't be happier with my current situation.

MGACSF: Where do you see yourself in five years?

Oliver: Hopefully doing something that I'm still happy with and not having the stress of a corporate job. Here, it's a different type of stress, but I love doing this, so I'm going to put in my best effort.