How The Simmons Trade Proves The Chicago Bears Learned Their Lesson

Blockbuster trades for veteran players are always a dangerous proposition. You’re giving up multiple high-value assets for one guy. Granted, that guy is usually a superstar, but it narrows the margin of error for your team. The Chicago Bears have been in this position before. In 2018, they flipped two 1st round picks to the Oakland Raiders for star pass rusher Khalil Mack. While it did lead to a division title that season, the Bears were never able to capitalize on it after that. They never finished better than 8-8 in Mack’s remaining three seasons with the team. Yet here they are again, this time trading two 1st round picks for Jeffery Simmons.

Why would they try this again after what happened with Mack? To answer that, it might be wise to look at similar trades over the year. I compiled a list of every major trade involving a 1st and 2nd round pick or more for a veteran player. Quarterbacks were excluded for a reason that will become clear. Here is a list of all those that qualified.

The Chicago Bears learned their lesson.

If you look at the list, there are three instances in which the acquiring team went on to win the Super Bowl after acquiring the player. In each situation, those teams had a proven quarterback. Jim Plunkett had won a Super Bowl in 1980 for the Raiders. Tampa Bay moved to Brad Johnson a year after adding Keyshaun. The same was true of Los Angeles, which traded for Matthew Stafford two years after securing Ramsey. In way too many of those situations, the acquiring team did not have a definite franchise quarterback under center.

That includes the Chicago Bears in 2018. They had seen nothing to that point indicating Trubisky was legit. It was his second season. They rolled the dice without any evidence, and it backfired on them after he regressed in 2019 and beyond. Way too many teams have done the same thing. Indianapolis just did it last year with Jones. For once, it looks like the Bears learned their lesson. General manager Ryan Poles didn’t make any big moves until he had a clear assessment of quarterback Caleb Williams.

Now that it appears the Bears have a budding star under center, they made the swing for Simmons.

The timing makes it even better.

If you look at the prominent quarterbacks on that list before Williams, all of them were on the older side when their teams went all out. Aikman was 34 and would retire after that season. Romo was 28, Wilson was 32, Prescott was 32, and Stafford was 38. Williams is by far the youngest on the entire list at 24. This isn’t a player who is on the downside of his career. He’s in the middle of ascending. So even if the Simmons trade doesn’t pan out, he’ll still be in his prime, giving the Bears ample time to retool.

More than anything, the process was sound. The Bears didn’t jump the gun this time. They made sure to assemble a young, talented roster through their draft picks and waited to see whether their quarterback would develop. Only once they were certain he was the real deal did they allocate the assets to get a difference-maker at a position of need. This is smart football. It is refreshing to see how the organization actually learned its lesson from eight years ago.