Jersey Jerry still winless on The Signs going into Week 4

Barstool didn't bury the lede on this one. The plug for Week 4 went out with the losing streak right up front: still looking for the first winner of the season.

Barstool Gambling

@stoolgambling

Week 4 Signs with @Jerrythekid21 Still looking for the first winner of the season @DraftKings #DKpartner

That's the bit, and it's a good one. The Signs is a weekly DraftKings segment with its own promo code, SIGN, and the sponsor is fine with the guy reading the signs having no winners to show for it a month into the season. The same clip went out on the main Barstool account and the clip accounts within 2 hours, all with the same line about the first winner. When the company is pumping your 0-for-the-season, the slump is part of the show.

The Signs is only half of Jerry's football gambling week. He also sits on Barstool Sports Advisors with Big Cat, the show that bills itself as America's premier sports information program, where he swings just as big. On the Week 3 episode on 2026-09-25, he went after the Jets and everybody who'd been calling them watchable this year.

Barstool Gambling

@BarstoolGambling

“Yeah, maybe watchable. But in this game, not watchable. They're going to get buried.” – Jersey Jerry

0:00

That's the Jerry everyone tunes in for: full conviction, a 4GP sign-off and not a single hedge. It's also the reason the Signs drought plays the way it does. A guy who talks like that and still can't hit a winner in September is a better watch than a guy grinding out a careful 55 percent, and Barstool knows it. Fading Jerry has been a running joke in his replies for years.

The frames don't show Jerry's Week 4 picks, so we won't guess at them. All that matters is whether his first winner finally comes this week or the streak gets another week of promos out of it. If it hits, expect a victory lap that runs longer than the segment. If it doesn't, Week 5's caption pretty much writes itself.