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The Ghost of What Could Have Been: Maxx Crosby and the Chicago Bears' Lingering Regret

  • Nishadil
  • February 20, 2026
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  • 4 minutes read
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The Ghost of What Could Have Been: Maxx Crosby and the Chicago Bears' Lingering Regret

Maxx Crosby: A Constant Reminder of the Bears' Missed Opportunity

The Chicago Bears' defense has often yearned for a dominant edge rusher. Maxx Crosby embodies that longing, serving as a stark reminder of a pivotal moment where their paths diverged, leading to perpetual 'what if' scenarios for fans.

Ah, the Chicago Bears. For generations, that name has conjured images of bruising defense, bone-rattling hits, and relentless pressure on opposing quarterbacks. It’s a proud tradition, etched into the very fabric of the NFL. But let’s be honest, in recent years, that storied defensive prowess, while still showing flashes, hasn’t always been consistent, particularly when it comes to finding that truly dominant, game-wrecking edge rusher, the kind who keeps offensive coordinators awake at night.

And that, my friends, brings us to the perennial question, the kind of hypothetical that stings a little more with each passing season: what if the Bears had landed a player like Maxx Crosby? You see, for Chicago faithful, Crosby isn't just another superstar defensive end; he's a living, breathing testament to a significant 'what if' moment, a constant reminder of a potential asset they could have had, and didn't. And that, in a nutshell, is the 'bad news' we're talking about.

Think back to the 2019 NFL Draft. The Bears, having traded their first and second-round picks for Khalil Mack the previous year (a move that, to be fair, paid dividends initially), finally stepped to the podium in the third round. They picked Riley Ridley, a wide receiver, at 73rd overall. Then, in the fourth round, at pick 126, they opted for linebacker Joel Iyiegbuniwe. Both were logical selections at the time, filling perceived needs. But just a little earlier in that same fourth round, at pick 106, the then-Oakland Raiders selected a rather unheralded defensive end from Eastern Michigan: Maxx Crosby.

It's easy to say now, of course, with the benefit of hindsight as clear as a sunny Chicago day. But few outside of the Raiders' war room could have predicted the absolute monster Crosby would become. He wasn't the flashiest prospect, perhaps lacking the elite athletic measurables that often send players rocketing up draft boards. What he possessed, however, was something far more invaluable: an unrelenting motor, a ferocity that borders on obsession, and a pure, unadulterated passion for getting to the quarterback.

Fast forward to today, and Crosby is not just a good player; he's elite. He's a Pro Bowler, an All-Pro, a captain, and the undisputed emotional leader of the Raiders' defense. His sack numbers are consistently among the league's best, but it's more than just sacks. It's the relentless pressure, the batted passes, the run stops, and the sheer disruptive force he brings on every single down. He plays with an intensity that's infectious, inspiring those around him. He is, to put it mildly, everything the Bears have often craved on the edge.

Imagine, for a moment, Crosby lining up opposite a healthy Khalil Mack (in his prime Bears years), or even pairing him with a burgeoning young talent on the current roster. The possibilities, the sheer terror he would instill in opposing offenses alongside Chicago's already tough defensive core, are tantalizing. But alas, it was not to be. The Bears passed, and the Raiders scooped up a generational talent in the middle rounds, a true diamond in the rough.

So, the 'bad news' for the Bears isn't some dramatic trade gone wrong or a last-minute reversal. It's the quiet, persistent sting of a missed opportunity in the draft. It’s the realization that a player who perfectly embodies the grit and defensive dominance Chicago fans adore was available, and they simply looked elsewhere. Building an NFL roster is an incredibly complex puzzle, full of tough decisions and unforeseen outcomes. But every now and then, a player like Maxx Crosby emerges, serving as a stark, sometimes painful, reminder of what could have been.

And for Bears fans, every time Crosby makes a game-altering play for the Raiders, there’s a collective sigh, a murmur of 'if only.' It’s a bitter pill to swallow, knowing a player of his caliber, with that kind of 'Bears grit,' could have been wearing the navy and orange, rather than wreaking havoc for someone else.

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