Jason “Pup” Reynolds has spent nearly two decades walking the fairways as a professional golf caddy — but his path to the bag was anything but ordinary.
From chasing his own dream as a young golfer to realizing his true calling, Pup shares how a two-week fill-in gig turned into a lifelong career. He reveals his first impressions of Dean Burmester’s talent, the chemistry that makes their partnership click, and why hearing the perfect strike is like “lighting a match.”
A story of passion, trust, and staying in sync when it matters most.
📍 Featuring: Jason “Pup” Reynolds & Dean Burmester
🏌️♂️ Shot at: LIV Golf event
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Jason Reynolds caddy, Dean Burmester, LIV Golf 2025, golf caddy stories, professional golf caddy, caddy life, golf partnerships, golf bag man, Stinger GC
My name is Jason Reynolds. Um, also known as Pup. Um, and I’m a professional golf caddy. I was never going to be an office guy. So, when I was a bit younger, 19, around about there, um, I was obviously striving to be a professional golfer, um, and came to the realization that I wasn’t good enough. So my old man said to me, “Well, you welcome to the world. You got to do something.” And my cousin’s a professional golfer. And he said to me, “Listen, just why don’t you just come carry my bag?” And and I just need somebody for these two weeks. And I just it stuck. I stuck with him 5 years and it just gradually I’m 19 years down the road now and I’m still doing it and I’m loving it. I think Burmy for me, I mean, his his talents, I think there’s a handful of guys that I’ve seen. I mean, I’ve seen a lot of golfers in my life, and you kind of know when you hear that that strike of a nine. It It’s just different. It’s like striking a match. It’s just It’s completely different to to the other players. And I’ve always I’ve always seen potential. like I always knew Dean was going to be really good. I always joked with his dad when I saw his dad. I said, “Listen, when are you going to let me take your son’s bag, so it was almost kind of like the stars aligned. Um, and yeah, we’ve never we haven’t looked back since.” And then there’s sometimes we we just click and we’re on the same wavelength and it’s kind of like you don’t need to say anything. You you know what the other person’s thinking and and when it’s like that, I mean, you’re on top of the world. It’s almost like a fairy tale. accompanied by his caddy Jason Reynolds.
3 Comments
Well done Jason!
You are now certainly reaping the rewards!
Dean has so far won 2 LIV Golf tournaments and placed highly on quite a few occasions. Stinger GC have also won the team competition maybe 3-4 times. Just the above comes to around $17 million (R300 million) and a caddie would earn 10% of that. So Jason’s doing great, and remember that is only over the last 30 months!
Awesome!!!
Mooi Gespeel Maat