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'I'm gonna look so bad after this': Matt Every explains why he once drove one OB . . . on purpose?

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Sam Greenwood

January 22, 2026
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If we've learned anything about Matt Every through the years, it's that when he's got a microphone in front of him, he's going to say something entertaining. We experienced that first hand when the two-time PGA Tour winner joined an episode of The Loop podcast a couple years back. And his latest pod appearance produced an all-time tour tale.

Every hopped on Golf's Subpar podcast earlier this week to talk about his, um, interesting career, and once again, he delivered plenty of golf. But we're going to focus on one funny—and kinda mean—story in particular.

As Every explains, he was in a "little tiff" at the time with his caddie, Derek Mason. And he was having a bad second round at the Memorial and on his way to a near-certain missed cut.

"I'm gonna look so bad after this," Every says with a chuckle before launching into the wild tale.

To set the scene, Every was coming off double bogey on the sixth hole (he played the back nine first) and Derek decided to forecaddie for him, hand him driver and not walk to the seventh tee with him (Every acknowledges it's a long walk, but that he hated when Derek forecaddied). After making his frustration known, another caddie in the group challenged him to hit one OB on purpose so Derek would have to walk all the way back to the tee to bring him another golf ball.

"(Brian) Stuard's guy goes, 'You won't hit one out of bounds on purpose," and was like, 'Yes I will. Which way do you want it? Right or left?'" Every recalls. "So we went right and I hit it right."

Classic. Listen to Every tell it hear, because that's not where the story ends:

"But the bet was he had to come back and hand me the ball, he couldn't, like, toss it," Every continues. "And he's coming up the hill and I'm not making eye contact with him the whole way and then he hands me the ball. And they all started laughing."

Poor Derek, but that's hilarious. And brilliant by Every if he managed to make a few bucks off a missed cut.