Ex-NFL star Dwight Freeney urges Maxx Crosby to consider leaving Raiders as $8B Chicago Bears seek game-changing pass rusher

For a long time, Maxx Crosby was the last player anyone expected to question his future with the Las Vegas Raiders. He played hurt, spoke about loyalty, and made it clear he wanted to be part of the franchise’s turnaround. That is why the current situation feels different. As the offseason approaches, Crosby’s name is suddenly at the center of trade talk.The reason is simple. Winning has not followed him. Crosby has done his part year after year, but the Raiders have not taken the next step. Tensions inside the locker room have grown, and recent events around his health only added fuel to the conversation. Former players are now openly wondering if staying in Las Vegas still makes sense for him.Former NFL star Dwight Freeney shared his thoughts on Up & Adams, focusing on what Crosby is missing most in his career. “The feeling of winning; there’s no feeling like that,” Freeney said. “When you win in the playoffs, and when you go to the playoffs, win a Super Bowl, those are the moments that stay with you forever.”The Raiders last made the playoffs in 2021. Since then, Crosby has collected Pro Bowl selections and signed a massive three-year, $106.5 million extension with $91.5 million guaranteed. His effort has never been questioned. His frustration, however, is becoming harder to ignore.Crosby injured his knee during the Raiders’ 31-0 loss to the Kansas City Chiefs in Week 7 but kept playing. In Week 17, Las Vegas finally shut him down against the New York Giants, placing him on injured reserve even though he wanted to stay on the field. Head coach Pete Carroll later said Crosby could also miss the season finale. Reports followed that Crosby wanted to leave the facility after hearing the decision.The timing matters. Crosby’s contract looks huge, but it is flexible. If the Raiders move him early in the 2026 league year, the dead-cap hit is small and the cap savings are large. After March 17, trading him becomes far more difficult. He also has no guaranteed money after 2026, which puts pressure on both sides to act soon.Trade ideas are already forming. Kay Adams has openly backed the Chicago Bears. “I’m rooting for him to be a Bear,” she said. “He’s a Michigan kid. He’s going to thrive in the cold, wherever that stadium is built.”Teams like the Baltimore Ravens, Dallas Cowboys, Los Angeles Chargers, Detroit Lions, and Cincinnati Bengals could also make sense. But, nothing is decided yet.Also read: Maxx Crosby trade talk heats up after Raiders’ surprising $5M contract reveal