Tuesday, December 16, 2025

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Bears Reportedly Had Planned To Go All In On Deshaun Watson

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Fate has a funny way of intervening sometimes. Three months ago, Deshaun Watson was considered the hottest commodity in the NFL. A disgruntled quarterback feeling jilted by a poor Houston Texans ownership. Eventually, he demanded a trade, sparking interest from several teams. However, new GM Nick Caserio refused to even take calls on the subject. He was not going to mark his name in the history books as the guy who traded Watson.

In hindsight, he probably regrets that decision now. On March 16th, the first of several sexual misconduct allegations involving Watson and message therapists surfaced. Suddenly his NFL career has been put on hold as he tries to fight what looks like a pretty ugly stain on his image. To say nothing of the dangers it poses to whether he’ll be able to play again at all. How different things might’ve been if Houston had acquiesced when they had the chance.

They certainly had their fair share of suitors.

According to Tyler Dunne of Go Long, the Chicago Bears were one of the most aggressive. While their resources weren’t viewed as great, Dunne has it on good authority the team would’ve done almost anything to secure Watson. The entire organization wanted him. They were willing to give up anything that wasn’t nailed down. Yet due to Houston stalling, the allegations hit and the Bears were forced to call off the pursuit.

The guy they really wanted was Deshaun Watson,” one league source told Go Long. “Before any of this stuff popped up, you better f—— believe they explored every possibility when that kid demanded a trade. You better believe they were the first team on the line saying, ‘What do you want?’ And that was the time Houston wasn’t taking any calls on him because he didn’t have a sexual assault thing hanging over him.”

By that point, the focus shifted to Russell Wilson who’d put forth a trade option to the Seattle Seahawks. It seemed like Chicago had a real shot at him before Pete Carroll intervened. All of these unfortunate close calls ended up funnelling the Bears towards the NFL draft where they finally pulled off the blockbuster move to secure Justin Fields with the 11th overall pick.

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Deshaun Watson saga may end up a blessing in disguise

Landing the superstar would’ve been great. Don’t get misunderstand. He’s a potential Hall of Fame-caliber player in his prime. By that same token, any price to acquire him would’ve been astronomical. So much that the Bears might’ve been without 1st or 2nd round picks for at least the next two years and perhaps three. For as good as Watson is, it is difficult to build a champion without any meaningful draft currency for such an extended period of time.

Nobody can say for sure if Fields will be anything close to Deshaun Watson in terms of NFL success. Yet he certainly has the talent. If he does follow a similar path, then the Bears have set themselves up for immense long-term success. Not just because of their ability to retain much of their future high draft picks but also not inheriting that massive contract Watson would’ve brought with him.

Maybe things worked out for the best.

Only time will tell. Watson remains embroiled in his legal battle and may not even play in 2021. So even if the Bears had somehow pulled off a trade it would’ve been looking like a massive mistake right about now. Instead, Fields is preparing for a training camp battle with Andy Dalton and the future is shining with hope. Fans are excited. Soldier Field should be full come the fall. This should be fun.

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