Monday just might be the most important day for the next 20 years of Chicago Bears football. That says a lot because the interviews that are rumored suggest a lot. Today, the Bears and Bill Polian will meet with Pittsburgh Steelers’ vice president of football and business administration, Omar Khan.

Many believe that Khan is the best option any team could hire, but he very well could be the NFL’s next great team executive. He has been a mainstay in the Steelers organization, but with some uncertainty moving forward, Khan may decide to move on to a new opportunity.

Khan has been with the Steelers for 21 years and has been an NFL executive since 1997. What I like most about Khan is, almost all he knows is success. Since the 2001 season (his first with the Steelers) his teams have made the playoffs 14 times, reached the AFC Championship game six times, played in three Super Bowls, and won championships twice. I like this because I 1000% believe being around success breeds success. There are only two other organizations that you could point to that have had this amount of success over the years, New England Patriots and the Green Bay Packers.

Some believed that when current Steelers GM Kevin Colbert steps down (expected after the draft), Khan was going to replace him. When there were rumors last season that Colbert could accept a role elsewhere, a story surfaced that Khan would be looked over and he was “not happy” with that decision. Now, with turnover apparent in Pittsburgh, it makes sense for Khan to explore other options.

Now, Khan is a numbers and accounting type of guy and is not a scout by any stretch. Most teams like their GM to be a scout first and put number crunchers in the back to work on the nerdy stuff. The Bears have notoriously been bad in controlling their cap, oftentimes going to their highest-paid players to restructure deals to open additional money. Having a strong cap man like Khan in place, the Bears could flip the structure and place all the scouts in the back with Khan out front.

What is very interesting, and why I think this could happen, is, Khan’s experience as VP of Football can allow for the Bears to move Ted Phillips to strictly a business role in the organization. George McCaskey has alluded to the idea that the GM would report directly to him, which moves Phillips out of any football-related decisions. The football buck would essentially end with Khan, and Phillips would be freed up to negotiate land contracts and making paper airplanes. The McCaskey’s also highly respect the Rooney family – probably more so than Polian – and any move that can steal a bit from the magic the Rooney’s have created would be a giant win for George.

The Bears would like to move quickly on a GM target with the Senior Bowl on February 5th. Having that role filled, and consequently, additional scouts and the rest of the front office personnel in place will be an important first step.

Because Khan is still under contract, if the Bears did elect to hire him, the Steelers would receive a 3rd round compensatory pick in either 2022 or 2023.

Will Khan be named the next GM of the Bears? I, and many other Bears fans, would approve. Strong theory one way or another, check out this betting app and place a bet on whom you think the Bears will hire.