Put Pinehurst on the Golf Trip Bucket List!
Kerry and Berkley welcome Tony Rudy to break down his annual Pinehurst trip — 15 guys, caddies, gambling, and some of the most diabolical greens in golf. What started as a friend's property gift in 2001 turned into a 12-time pilgrimage to Pinehurst, NC.
- Guest
- Tony Rudy
- Destination
- Pinehurst Resort, Pinehurst, North Carolina
- Location
- NC
The Setup
Kerry and Berkley welcome Tony Rudy to the pod to break down his annual Pinehurst golf trip — 15 guys, caddies, gambling, and some of the most diabolical greens in golf. Tony shares how a friend’s property gift back in 2001 turned into a 12-time pilgrimage to Pinehurst, North Carolina.
The Format
We dig into what makes a trip like this run: caddies and walking, the pro experience, the formats and gambling games that keep 15 guys honest, and the group dynamics that hold a tradition like this together year after year. Tony also walks through the ideal 5-day / 4-night itinerary and the best courses to build the trip around.
The Hot Takes
- What makes Pinehurst No. 2 special — and why No. 4’s greens might be harder
- The infamous greens and the wild drainage that gets them tournament-ready 10 minutes after a storm
- Legendary caddy stories (including the Fred Couples divorce-serve) and the Cradle par-3
- Three birdies on Number 2
- The rain story
- Cost breakdown, food, and nightlife — Beehawk and the new distillery from a Black Hawk Down veteran
- The 18th-hole veranda
The Run-It-Back
We close with the course rating, the best team format, and the host FOMO scores — where a 12-times-and-counting tradition lands on the bucket list, and how to book tee times without needing a member hookup. After a dozen trips, the run-it-back question mostly answers itself.