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.
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!"
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.
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.
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.
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.