Dave Portnoy's team routs Jon Gruden 5UP in DraftKings grudge match

Barstool's #DKDay Grudge Match, presented by DraftKings, turned into a rout on Wednesday. Team Portnoy jumped out early and never let go, and by the back nine the broadcast graphics were basically doing a victory lap for them while Jon Gruden's group tried to find any putt that would drop.

Dave Portnoy

@stoolpresidente

What a choke!

That putting misery wasn't a one-hole thing. Barstool's own account called it "one of the worst putting performances in history," and Pardon My Take piled on with the green team unable to "make a putt to save their lives." Gruden himself didn't fight the narrative — he posted his own "Tough day on the greens" tweets as his side fell 3 DN and then 5 DN over the middle holes, conceding it flat out: "Not our day!"

Jon Gruden

@BarstoolGruden

Not our day! @DraftKings #DKPartner

Team Portnoy's lead ballooned to 5UP and stayed there through a wild finishing stretch. Whitney had a putt to end the match outright and pushed Dave to go for the kill — "Do it Dave, end the Grudge Match," with Dave firing back that he'd "never wanted to do anything more" in his life. Whitney also got his own crack at a match-clinching putt but couldn't finish it, and the celebration ultimately came a couple of holes later once Team Portnoy sealed the 5UP win for good.

Barstool Sports

@barstoolsports

Whit: Do it Dave, end the Grudge Match Dave: I’ve never wanted to do anything more in my life #DKDay

Gruden, who signed a multiyear deal with Barstool back in November 2024 and has since become a fixture across the site's content, took the loss with good humor — tipping his cap to "Team White" for being "dialed in today." Big Cat, for his part, made sure to credit the actual hero of the day rather than take a bow himself, thanking Ryan Whitney directly for a win he admitted he didn't deserve on his own game.

Big Cat

@BarstoolBigCat

Great grudge match. Grudged so hard. I’m terrible at golf but I’m a winner. Thank you to @ryanwhitney6

And because no Barstool golf outing is complete without chaos, an old clip resurfaced of Pug driving a golf cart straight across the putting green — a reminder that etiquette has never been this crew's strong suit, win or lose.

Viva La Stool

@VivaLaStool

Throwback to the time Pug drove on the green

Portnoy closed the day the way he closes most golf outings — by declaring himself done with the sport forever, at least until the next Grudge Match rolls around. "Breaking: Dave Portnoy has retired from @DraftKings Grudge Match tournaments," he posted, a joke that's become something of a tradition after every win. Given how lopsided this one got, don't expect that retirement to stick any longer than the last one did.