335: Recapping Smylie's Pebble Beach Trip + Russell Henley Wins Colonial In Playoff

The Smylie Show19mMay 31, 2026
AI-Generated Summary

The Smiley Show dives into a whirlwind weekend of golf highlights, starting with Smiley Kaufman's personal experience at Pebble Beach—where he hit a stunning 225-yard three-iron into the 18th green against a strong headwind, salvaged a par after a shaky short game moment, and reflected on the dramatic 115,000-pound cypress tree transplant from Spyglass to Pebble Beach’s 17th hole. The episode then shifts to a deep recap of Russell Henley’s playoff victory at the Charles Schwab Challenge, where Henley’s clutch putting and composure under pressure—especially after a shaky front nine—earned him his first win since 2021. The hosts analyze Henley’s mental resilience, contrast him with near-miss players like Eric Cole, and spotlight rising contenders like Ryan Gerrard and Ben Griffin, whose confidence and ball-striking remain strong despite missing the playoff. Looking ahead to the Memorial Tournament and the upcoming U.S. Open, the show identifies Colin Morikawa and Gary Woodland as key players to watch, citing their form, course fit, and ability to thrive in tough conditions. The episode closes with a surprise merch drop: two new Imperial-branded hats, including the Smiley Ball Tour Visor, now live for fans to purchase. The most striking takeaway isn’t just Henley’s win or the tree transplant—it’s the idea that elite golf success often hinges not on raw talent, but on the ability to execute under pressure, recover from mental lapses, and maintain consistency through adversity.

Key Takeaways
1

Russell Henley won the Charles Schwab Challenge in a playoff by making multiple clutch putts, proving that mental toughness trumps raw talent when the pressure mounts.

2

Smiley Kaufman hit a 225-yard three-iron into the 18th green at Pebble Beach into a 15 mph headwind—his best shot of the trip—after a shaky short game start.

3

A 115,000-pound cypress tree was successfully transplanted from Spyglass to Pebble Beach’s 17th hole, a logistical feat involving tree experts, wind routing, and power line clearance.

4

Ryan Gerrard, despite a strong putting week, fell short in the playoff, but his consistent ball-striking and confidence suggest he’s close to breaking through professionally.

5

Colin Morikawa and Gary Woodland are emerging as top contenders for the U.S. Open, with Woodland’s long iron play and wind-fighting ability making him a strong fit for Shinnecock.

…and 3 more takeaways available in PodZeus

Chapters
0:19
2 min

Opening Chaos: Denver Airport & Smiley’s Pebble Beach Debut

The episode kicks off with chaotic energy from the Denver Airport food court, setting a playful tone. Smiley is live from the airport, joking about conspiracy theories and setting up the week’s main topic: his Pebble Beach trip.

2:22
2 min

Pebble Beach First Tee: Cold Turkey & a 6 a.m. Challenge

Smiley recounts his early tee time at Pebble Beach—6 a.m.—with no warm-up, cold turkey, and a chilly start. He hits a controlled snap hook and a perfect driver, setting the stage for an emotional and physical test.

4:05
2 min

The 115,000-Pound Cypress Tree Transfer: A Golfing Feat

That's super cool. All right, well, how about that? Good golf weekend for Smiley.

Highlight
5:40
2 min

Smiley’s 225-Yard Three-Iron at 18: A Shot for the Ages

This thing is absolutely beautiful. So, you know what I ended up doing from there? It was right at the front of the green and you know I feel cocky, a little confident.

Highlight
8:03
2 min

The 'Derf' on 18: When Confidence Crumbles

I just stopped turning and just that 56 degree just went right down the bottom. And I use a 56 so much more consistency, right?

Highlight
High-Impact Quotes
But, you know, that's it means a lot to these guys, you know, to be able to practice and prepare and then get into that situation where you have a chance and then you're able to execute and make the putts.
Host11:18
This thing is absolutely beautiful. So, you know what I ended up doing from there? It was right at the front of the green and you know I feel cocky, a little confident.
Smiley Kaufman7:08
I just stopped turning and just that 56 degree just went right down the bottom. And I use a 56 so much more consistency, right?
Smiley Kaufman8:18
Speakers

Host

Smiley Kaufman
Topics Discussed
pebble beach golf course90%clutch putting in golf88%russell henley playoff win85%golf merch launch82%tree transplant golf80%golf course renovations75%us open preparation75%memorial tournament preview70%
People & Brands

Smiley Kaufman

person

12xNeutral

Pebble Beach

place

10xNeutral

Russell Henley

person

8xPositive

Imperial

brand

5xPositive

Charles Schwab Challenge

other

5xPositive

Colin Morikawa

person

4xPositive

Gary Woodland

person

4xPositive

Spyglass Hill

place

4xNeutral

Ryan Gerrard

person

3xNeutral

Ben Griffin

person

3xPositive

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