Jay Cutler had one of the most checkered careers for a quarterback in NFL history. He ascended to Pro Bowl status by his third season in Denver. Then the Broncos hired a new head coach in Josh McDaniels who insulted him in their first meeting together. This led to his demanding a trade. He came to Chicago, set the modern team record for interceptions in a season in his first year, and then led them to the NFC championship his second.

Cutler feuded with offensive coordinators and wide receivers. He had epic comebacks and all-time clunkers. The guy was a walking enigma. One who divided the Bears fanbase like few others in history. Half the people loved him. Half hated him. The man probably had a lot of bad memories throughout his career. Yet none rivaled his two years under Marc Trestman in 2013 and 2014 in terms of sheer lunacy. When asked on Red Line Radio if that was the weirdest experience of his football life, his answer says it all.

“By far. Not even close.”

Hard to argue that.

So what exactly was it? Was Trestman just a complete buffoon? Not exactly. Cutler made it clear he didn’t hate Trestman as a person. The primary issue stemmed from the coach’s naivete. He didn’t understand the type of athletes he was dealing with in Chicago. The CFL type of football player he’d grown used to years prior was nothing like NFL players. Trestman became too focused on building a culture of self-improvement on and off the field. That was his fatal mistake.

“The locker room was in disarray. The locker room was a complete and utter shitshow. I like Marc. We got along. It’s just that he had a different philosophy. The NFL…it’s just…it’s business. You either perform or you don’t perform. You obviously have to be kind of a good human but there’s some dudes who just run crazy in the NFL. Off the field, they do whatever they want then they come in and get the job done. It is what it is.

Marc kind of wanted to create a culture that was better humans. That’s great if you’re winning. As soon as you’re not winning? It’s a problem. Guys are like, ‘I’m here to win. I’m here to get paid and I’m here to win. I don’t care about becoming a better human right now.’ So that’s where it all fell apart.

We started losing games that second year and that was it. The wheels fell off and there was no getting it back.”

In simple terms, Trestman lost track of the bottom line. Most NFL players, they’re in the business of winning. If that doesn’t happen, they get cranky fast. When certain guys get cranky, they also get rebellious. They get outspoken. This leads to divisions in the locker room and before long any semblance of team unity is gone. Trestman was completely unprepared for that and it showed during the awful disintegration of the team in 2014.

This might explain why Jay Cutler likes Matt Nagy

The latest Bears head coach has demonstrated character traits that Trestman seemed to lack. Namely, the one where he’s able to command a locker room during the tougher periods of a season. Look no further than 2020. After a 5-1 start, the Bears went into a tailspin that saw them lose six-in-a-row at one point. If that had been Trestman? Odds are the team wouldn’t have won another game the rest of the year.

Instead, Nagy managed to rally them to a three-game win streak. Just enough to go 8-8 and make the playoffs. Given the mindset of NFL players, that is difficult to do. Maybe things could’ve been different for Jay Cutler back then if Nagy had been ready to coach. It would’ve been fascinating to see how he would’ve handled the likes of Brandon Marshall and Martellus Bennett.

We’ll never know.

Cutler certainly doesn’t seem overly bitter about the experience. Even if he has good reasons to be. The quarterback was victimized for a lot of the problems that team went through. This despite evidence the fissures ran far deeper. Such is the nature of being the quarterback. It just underscores how poor the decision to hire Trestman was in the first place.