All Episodes

June 13, 2026 22 mins

Do you ever wonder what the caddies get up to when the cameras stop rolling and the PGA Tour players head to the clubhouse?

In this live episode from the RBC Canadian Open, host Colin Weston steps inside the Caddie Lounge (powered by [Levelwear](www.levelwear.com)) to uncover the gritty reality of life on the bag with 28-year tour veteran Don “Double D” Donatello.

From carrying 42-pound golf bags up the equivalent of 60 flights of stairs a round to a dramatic "I quit" moment on the 4th hole, Don shares the wild, unfiltered stories of 650+ tournaments and why this lounge is a game-changer for professional caddies.

Key takeaways in this episode with Don that you will discover:
The Harsh Math of Caddie Economics:
Don breaks down the financial gamble of being a looper - the low base salary, paying your own travel expenses, and how missing the cut means earning $0 for a week’s work.

The Physical Toll of Looping:
It’s not just walking. Don reveals the insane fitness stats: 18,000+ steps and 30-60 flights of stairs per day, all while balancing a 42-pound bag on uneven terrain.

How the Caddie Lounge Was Born:
Learn how a simple conversation over a Levelwear hat turned into a tour-wide movement, giving caddies their own space with massage therapists, video games, and the dignity they’ve deserved for years.

The Caddie Lounge at The RBC Canadian Open is Levelwear's way of supporting their "Who's With You?" campaign to provide PGA Tour caddies with a space to unwind, rejuvenate and hang out with their fellow loopers. The Caddie Lounge is now at over 10 PGA Tour stops annually.

Three Inspiring Quotes from Don Donatello
On the old days vs. now:
"28 years ago, I only got paid $400 a week. You drove in a car and slept three to a room. One guy would sleep on the floor and you had to stand outside in the rain. Now, thanks to Levelwear, we feel like we’re being treated like the players."

On the secret to a long career:
"Certainty out here is very important as a caddie. A lot of mistakes these PGA Tour players make aren’t because they not good - it’s because they’re uncertain. Knowing when to speak and when not to is a very fragile thing."

On saving Webb Simpson’s career:
"He had four holes to play to keep his card. I changed his read on two putts. He made both. He shot 63 to keep his card. He said, 'Those were some of the greatest reads ever!'"

Episode Chapters
00:00 – Live from the RBC Canadian Open: Welcome to the Caddie Lounge
01:15 – Meet Don “Double D” Donatello: 28 years, 31 bags, 650+ events
02:30 – The Birth of the Caddie Lounge (and the “Who’s With You” campaign)
05:20 – Then vs. Now: **Sleeping on floors to massage tables
**07:05 – The brutal physical stats:
42lbs, 18k steps, and 60 flights of stairs
09:15 – Don’s origin story: From best player at the club to caddie
10:20 – The economics of looping: Base salary, expenses, and betting on your player
13:05 – Don's Proudest moment: The Webb Simpson story (changing reads to save a card)
15:05 – The “I Quit” story: Walking off the course mid-round
18:05 – How new caddies get jobs (agents, veterans, and the Korn Ferry grind)
21:05 – Inside the prep work: How Don and Tom Hoge tackle a new course
24:35 – The therapist role: Knowing when to talk and when to shut up
26:12 – Wrapping up and wishing Don luck at The RBC Canadian Open

Listen
Watch
Mark as Played

Advertise With Us

Popular Podcasts

Stuff You Should Know
Betrayal Weekly

Betrayal Weekly

Betrayal Weekly is back for a new season. Every Thursday, Betrayal Weekly shares first-hand accounts of broken trust, shocking deceptions, and the trail of destruction they leave behind. Hosted by Andrea Gunning, this weekly ongoing series digs into real-life stories of betrayal and the aftermath. From stories of double lives to dark discoveries, these are cautionary tales and accounts of resilience against all odds. From the producers of the critically acclaimed Betrayal series, Betrayal Weekly drops new episodes every Thursday. If you would like to share your story, you can reach out to the Betrayal Team by emailing them at betrayalpod@gmail.com and follow us on Instagram at @betrayalpod and @glasspodcasts. Please join our Substack for additional exclusive content, curated book recommendations, and community discussions. Sign up FREE by clicking this link Beyond Betrayal Substack. Join our community dedicated to truth, resilience, and healing. Your voice matters! Be a part of our Betrayal journey on Substack.

Dateline NBC

Dateline NBC

Current and classic episodes, featuring compelling true-crime mysteries, powerful documentaries and in-depth investigations. Follow now to get the latest episodes of Dateline NBC completely free, or subscribe to Dateline Premium for ad-free listening and exclusive bonus content: DatelinePremium.com

Music, radio and podcasts, all free. Listen online or download the iHeart App.

Connect

© 2026 iHeartMedia, Inc.

  • Help
  • Privacy Policy
  • Terms of Use
  • AdChoicesAd Choices