DiscoverThe Drop by The Caffeine CaddyEpisode 9: Golf’s Heartbreak Club: The Best Who Never Won
Episode 9: Golf’s Heartbreak Club: The Best Who Never Won

Episode 9: Golf’s Heartbreak Club: The Best Who Never Won

Update: 2025-06-25
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This week on The Drop, we’re recapping all the drama from the Travelers Championship, including Tommy Fleetwood’s latest heartbreak and Keegan Bradley’s fiery win at TPC River Highlands. We break down the final round, the clutch shots, and why Keegan plays golf like a baseball closer.

Then, inspired by Tommy’s near-miss, we dive into golf’s most frustrating club — the best players still searching for that elusive PGA Tour victory or major championship. From Fleetwood and Rickie Fowler to Colin Montgomerie and Max Homa, who’s the most overdue? And who’s next to finally break through?

We also stir in some Ryder Cup debate, Keegan’s captaincy chances, and of course - a little caffeine talk to round things out.

Caffeine Corner:
In this week’s Caffeine Corner, we kick around a hypothetical every golfer’s dreamed about for their own game 

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Episode 9: Golf’s Heartbreak Club: The Best Who Never Won

Episode 9: Golf’s Heartbreak Club: The Best Who Never Won

The Caffeine Caddy