They say everything’s bigger in Texas, especially when it comes to NFL drama. Jerry Jones has never been one to shy away from placing monster bets. Sometimes he wins hearts, sometimes he triggers a collective groan from the star-wearing faithful. Colin Cowherd summed it up perfectly: “This is a personality trait. Jerry Jones loves to save. He loves to give people jobs that need him. – He feels like the rest of the league is out, I am in, and I think that’s why the Cowboys are where the Cowboys are currently in the NFL.” But Jones’ offseason move to get George Pickens, thought to be the biggest addition to the Dallas offense, could be a cause for major concerns in the immediate future.

Dak Prescott is excited to have a new weapon to stretch the field and create mismatches with Pickens. Even the Cowboys’ star WR CeeDee Lamb shut down hierarchy talks, touting himself and Pickens as WR1s. With his explosive performances, Pickens has seen two postseason games during his tenure with the Steelers. But as far as player conduct goes, Pickens wasn’t exactly your knight in shining armor. He’s more the enigmatic receiver with a folder full of red flags. Steelers’ HC Mike Tomlin tolerates red flags up until the point of no return. But in last season’s Week 13 win against the Bengals, Pickens was flagged for ‘unsportsmanlike conduct’ twice. Even the HC had to say Pickens “has gotta grow up.” And analysts now fear history could repeat itself in Dallas.

The Athletic’s Vic Tafur shared his predictions and best bets in the NFL this year. Tafur put the Cowboys under 8.5 (-140), and among the reasons for Jerry Jones’ headaches, the trade for George PIckens was a major one. Tafur backs it up with history as he writes, “Dallas did trade for George Pickens, who on paper is a perfect fit – a deep threat to line up opposite CeeDee Lamb and take advantage of Dak Prescott’s big arm. But Mike Tomlin had reached the end of his wits with Pickens in Pittsburgh, and the last time he let a star player leave, Antonio Brown showed up with scorched feet in a hot air balloon and put the Raiders through hell.”  That ‘hell’ could now be brewing in Dallas with Pickens. And if Brown’s history in the Steel City was any indication, things aren’t looking good.

During his stint with the Steelers, even his teammates noted the only reason Tomlin was putting up with Brown’s off-field antics and drama was because of the explosive performance he was giving on the field. But there’s only so much you can ignore. As Ryan Clark remembered an instance from 2012 training, Brown had gotten into a heated argument with the then-DC Dick LeBeau. He even shouted at the defensive players gathered: “Don’t touch me. I’m the franchise.” And that’s just one instance. His 9 year stint with the Steelers was full of scrapes with teammates, coaches, and off-field antics. The same streak followed him when he got traded to the Oakland Raiders in 2019. Missed training camp sessions, arguments with the team, and even grievances with the league for his helmet. The list went on till the Raiders released him in September.

George Pickens’ stint with the Steelers was nothing different. And something similar could quickly turn the optimism sour for Jones. If Tomlin finally decided to part ways with Pickens, Dallas should have probably paused and taken a closer look at the warning lights. But a WR with red flags isn’t the only cause for concern now. Jones has made some gambles throughout the offense, and the price to be paid for that could be very high.

The run game headache for Jerry Jones

Dallas has faced its share of ups and downs, veterans retiring, young names vying for a roster spot; they’ve seen it all this offseason. But the offense’s decision to let a key piece go could come back to haunt Jerry Jones and Co. Letting Rico Dowdle walk in free agency didn’t just thin the running back room. It signaled a bet on new contributors and untested depth to keep the ground game rolling. As Vic Tafur further noted in his assessment, “We’re also concerned with the running game, as the Cowboys will regret letting Rico Dowdle walk. This season will hit the rocks during a brutal Week 12 through 15 stretch where the Cowboys play the Eagles, Chiefs, Lions, and Vikings and Jerry Jones starts openly pining for Arch Manning.” 

Dowdle’s physical style and ability to churn out tough yards in clutch moments offered much-needed balance to Dak Prescott’s passing attacks last season. Dowdle’s career-best 1,000+ yard season speaks for itself. But he’s running with the Panthers now, and without him, Dallas is banking on either a rookie learning curve or a host of backs without proven production in late-season pressure. The risk? When crunch time hits, especially against a slate of top-tier defenses like Philadelphia and Kansas City, every first down will count. Mistakes in the run game could quickly spiral out of control. As the stretch unfolds, the backfield issues could even push Jones to look for a savior in a new QB.

For a franchise so often defined by its offensive prowess, watching the attack slip just as playoff hopes are on the line would sting even more. The pressure is on for this rebuilt Cowboys offense to prove the skeptics wrong before the regret bill comes due. How will it pan out? We may see some flashes of it in training camp or the preseason.