Orange team wins DraftKings Road Trip championship

The DraftKings Road Trip has a champion, and it came down to the wire. Orange Team was trailing in the final challenge before rallying to steal the title away from Black Team, capping off a multi-stop, multi-week sponsored trek across the country.

Barstool Sports

@barstoolsports

The Orange Team comes from behind to win the final challenge! They are the 2026 #DKRoadTrip Champions

The reactions came fast. Mike Katic posted that there was "never a doubt" for the Orange squad, while Dana Beers demanded the bonus bet that comes with a title and Megan summed up the whole trip as a ride literally paid for by DraftKings. Big Cat even brought the hardware onto the podcast set, referencing a callback bit that got a redo this year.

Viva La Stool

@VivaLaStool

“Brandon you said that we didn’t do it well last time so we fixed it” -Big Cat

Winning didn't end the content pipeline — it just kept it moving. The Dana Tries series, DK's ongoing sponsored taste-test bit, rolled out a fresh round of stops this week, from fried boudin balls at a barbecue stop to a tofu tasting that got a decidedly less enthusiastic reaction on camera.

Dana Beers

@danabeers

Dana Tries Tofu #DKPartner

The road trip stops themselves kept producing chaos on their own. At one point the crew nearly lost Jersey Jerry to a boa constrictor during a reptile-exhibit challenge — comedic hyperbole, but the snake and the nerves were both very real.

Barstool Sports

@barstoolsports

Can you hold a boa constrictor for one minute? We almost lost Jersey Jerry to this #DKRoadTrip challenge

Then came the part nobody wanted: getting home. Kelly Keegs documented a genuinely miserable United ordeal trying to get back to NYC, from a delayed departure to a ground stop at LaGuardia to sitting on a boarded plane for a 7-hour delay before the captain added another 40 minutes on top of it. TJ Hitchings had his own United nightmare running parallel, stuck at O'Hare for 6 hours before finally taking off, and Big Cat fired off his own frustration at the airline in the middle of it all.

Kelly Keegs

@kellykeegs

Fuck. LaGuardia at a ground stop now. Not boarding yet.

By the time Keegs landed, it had been an 18-hour travel day — for a trip that was supposed to end with a trophy, not a red-eye horror story. She called herself "a shell" of the person who left, which tracks: winning the DK Road Trip was apparently the easy part.