The Chicago Bears have earned skepticism.

Few people trust them to make the right decisions, particularly regarding quarterbacks. We’re talking about one of the NFL’s most historic franchises. We’re also talking about a franchise that has repeatedly committed malpractice when drafting and developing the most important position in sports.

If any other team had two high draft picks— the No. 1 and No. 9 overall selections—and a tradable asset, we’d be bullish on their future. Chicago could play it safe by taking the presumptive top draft choice USC’s Caleb Williams and trading Justin Fields. Seems obvious and it could also be the correct move, one that reenergizes a starved, football-crazy town.

But these are the Bears. Virtually every quarterback decision they have made over decades has been wrong. The most painful reminder occurred when the Pittsburgh Steelers released Mitch Trubisky last week. That transaction occurred just a day after Patrick Mahomes won his third Super Bowl for the Kansas City Chiefs.

Trubisky and Mahomes will forever be connected. In the 2017 draft, the Bears traded up to the No. 2 overall pick to take Trubisky. Later on, the Chiefs traded up for Mahomes at No. 10 overall. Those two decisions continue to haunt Chicago. That’s the most recent example of why Bears fans don’t trust their team. After all, the Bears drafted Rex Grossman and Cade McNown in the first round.

But past incompetence doesn’t mean Chicago is doomed to failure if it takes Williams. The 2022 Heisman Trophy winner is considered a generational quarterback prospect, possibly the best since Andrew Luck (2012) or Peyton Manning (1998). If Chicago general manager Ryan Poles believes that’s true, he must take Williams and hope coach Matt Eberflus and newly hired offensive coordinator Shane Waldron can nurture Williams into a star.

There’s also the possibility that Chicago could take North Carolina’s Drake Maye at No. 1 or trade down for LSU’s Jayden Daniels or Michigan’s J.J. McCarthy. 

Regardless, picking a new quarterback would likely mean shopping Fields.

Fields, 24, being in play changes a lot. Starting quarterbacks are always in demand and young quarterbacks on cheap contracts are particularly valuable. Fields is in the fourth year of his rookie contract with a fifth-year team option. It might be worth it for a QB-needy team like the Atlanta Falcons, the Pittsburgh Steelers, the Las Vegas Raiders, or the New England Patriots to take a one-year flyer on Fields.

A change of scenery might benefit Fields, who has been hindered by poor coaching and a thin supporting cast. In Atlanta, he would be surrounded by the most talented young skill positions players (Bijan Robinson, Kyle Pitts, and Drake London) he has ever had. In Pittsburgh, Fields would have a strong coaching leader in Mike Tomlin and stability.

Someone will take a chance on Field and hope for the best. This might be a win-win for him and Chicago.

However, this is also the remote possibility that Chicago will stick with Fields. Maybe the Bears will do what they did last year when they traded the No. 1 overall pick to the Carolina Panthers. We will forever wonder what the Bears would have done. Would they have taken Bryce Young or C.J. Stroud? Even if they did select Stroud, there’s no guarantee that he would have developed into the NFL Offensive Rookie of the Year.

The draft is two months away. Chicago’s quarterback decision will shape the league in 2024 and perhaps for years to come.

About Michael Grant

Born in Jamaica. Grew up in New York City. Lives in Louisville, Ky. Sports writer. Not related to Ulysses S. Grant, Anthony Grant, Amy Grant or Hugh Grant.