Dave Portnoy puts Greg Olsen in awkward spot with Tony Romo bait

Greg Olsen must know his stock is soaring as Tony Romo’s is plummeting, but that doesn’t mean he wants to address it publicly.

Olsen appeared on FS1 for his weekly segment alongside Dave Portnoy and Jon Gruden on Wake Up Barstool Monday morning. And just before Olsen signed off, Portnoy offered some praise that put the NFL on Fox analyst in a bit of an awkward position.

“Greg, your stock keeps going up!” – @stoolpresidente https://t.co/BRJiK3suYA pic.twitter.com/Q4scJ0bZ5O

— Wake Up Barstool (@wakeupbarstool) January 12, 2026

“Greg, your stock keeps going up,” Portnoy commended Olsen. “There’s a guy on the other network… he looks like he’s on drugs or something when he’s calling games. Your stock is going up. So, congrats for that.”

That guy on the other network is presumably Tony Romo. And while it would have been great content if Olsen echoed Portnoy’s sentiment and bashed Romo, he opted to take the high road, only giving a slight smirk before saying goodbye and signing off. But Wake Up Barstool’s Brandon Walker and T-Bob Hebert were quick to note Portnoy put Olsen in a tough spot by bringing up Romo.

“It’s a different network!” Portnoy interjected. “He didn’t say it, I said it. I mean, come on. What was Romo talking about? Tony Romo started that game off with the most nonsensical rant I ever heard.”

Romo was doomed from the start Sunday afternoon. He opened the broadcast alongside Jim Nantz by awkwardly claiming the Jaguars could pull off an upset against Buffalo just as the 10-point underdog Carolina Panthers almost did against the Los Angeles Rams a day earlier. The problem, however, is that Jacksonville began the game as the betting favorite to win.

And from there, Romo wouldn’t recover. The $180 million lead analyst for CBS continued to confuse viewers throughout the broadcast, garnering widespread criticism from NFL fans and media. Just don’t expect Greg Olsen to add any fuel to the fire.

Romo’s stock has been dipping for years. But the accrued depreciation is reaching the point where CBS should be having some serious conversations about whether they can continue running Romo out there as their top analyst next season, especially with J.J. Watt looming.