The Chicago Bears quarterback legacy is almost as defined by their near-misses of greatness as they are their whiffs on terrible QBs. The likes of Jim Harbaugh, Cade McNown, Rex Grossman, and Mitch Trubisky were among many crushing disappointments. Yet an even greater pain comes from knowing how close the organization came to getting it right. Terry Bradshaw being a coinflip away in 1970. Having Joe Montana’s draft card ready to turn in during the 1979 draft. Failing to meet with Kurt Warner in 1997 because of a spider bite. The list is extensive. Now a new name apparently must go on it. Brett Favre.

Yes, really. This isn’t about him back in the 1991 draft or being available for trade a year later before anybody knew what he was. No, apparently the Bears’ opportunity came almost two decades later. After having just taken the Green Bay Packers to the NFC championship in 2007, Favre initially felt like it might be time to retire. He even said as much the subsequent March. However, by July he’d changed his mind and was hoping to return.

The Packers weren’t keen on that idea.

They had Aaron Rodgers waiting in the wings and were tired of Favre’s constant flirtations with retirement. So the Hall of Fame QB sent a letter to the organization asking for his unconditional release. This is where it gets interesting. Peter King of NBC Sports revealed that then-GM Ted Thompson refused to do that. Not because he wanted Favre back though. It was because he knew what would happen if he granted the request.

“When Favre was demanding his freedom from Green Bay after coming out of retirement in July 2008, then-GM Ted Thompson insisted he wouldn’t cut Favre loose. He knew Favre would likely sign with Minnesota or Chicago, and Thompson didn’t want to be hung in effigy in Wisconsin. He held firm, and Favre got traded to the Jets before eventually ending his career as a Viking.”

Everybody knew the Vikings were in play from the start. Their offensive coordinator, Darrell Bevell, had been a quarterbacks coach in Green Bay from 2000 to 2005. He had direct ties to Favre. The Bears though? That is a bit of a surprise. The idea is Favre was likely looking for any team that would give him a chance to face and beat the Packers. Chicago would make sense in this regard. They’d just gone to the Super Bowl two years prior and were 6-2 against Green Bay since 2004.

Brett Favre arrival would’ve changed so many things

By far the biggest being the fate of Jay Cutler. If Favre had come to Chicago in 2008, there is no way the Bears trade for the disgruntled Denver Broncos quarterback in 2009. That means they hang onto the 1st round picks they gave up. How interesting it would’ve been to see where they would’ve gone with those. Then the question becomes could that team have made one more run at the Super Bowl?

Brett Favre had an uneven year in 2008 with the Jets, throwing 22 touchdowns and 22 interceptions. However, a lot of that was due to an injury in his throwing shoulder. He was playing well through the first 11 games with 2,461 yards, 20 TDs, and 13 interceptions. Things changed when he tore the bicep tendon in his shoulder. This led to nine interceptions and just two TDs over the final five games. Maybe that injury doesn’t happen in Chicago.

Then the next year, Favre had one of his best seasons.

Over 4,200 yards, 33 touchdowns, and just seven interceptions. The Minnesota Vikings reached the NFC championship game. Considering the Bears went 9-7 with Kyle Orton in 2008 and were in the NFC championship themselves in 2010? It isn’t a stretch to think they could’ve made it back to the Super Bowl in that brief window before Favre finally fell apart.