The Bears would sign Glennon, according to initial reports on Thursday from Adam Schefter of ESPN and Ian Rapoport of NFL.com.
According to Schefter, the deal will be for a total of $45 million, and Rapoport reports that it includes a guaranteed $18.5 million spread over three years. “Glennon’s three-year, $45 million deal is basically a one-year, $16 million deal with team options for 2018 and ’19,” according to Albert Breer of TheMMQB.com on Friday morning.
According to Dan Wiederer of the Chicago Tribune, the action was taken the same day the Bears cut veteran quarterback Jay Cutler.

The team’s starter, 2015 No. 1 overall pick Jameis Winston, has been outstanding and reliable, while Glennon, 27, has only completed 11 passes in the previous two seasons. Glennon is now merely a backup for Winston, who is now the organization’s face.

Originally selected in the third round of the 2013 NFL draft, he was once considered the team’s future. However, he never really cemented the job in 19 games over the 2013–14 seasons, throwing for 4,025 yards, 29 touchdowns, and 15 interceptions on just 58.8% of his passes completed.

In contrast, in his two seasons as a quarterback, Winston has thrown for 8,132 yards, 50 touchdowns, and 33 interceptions. He guided the Bucs to their first winning campaign since 2010 this year.
The Buccaneers hired Sean Renfree in late January to round out the quarterback depth chart behind Winston, most likely anticipating that Glennon would leave in free agency this offseason. Glennon was disposable because Ryan Gryphon is still a member of the team.

Another major reason for his departure is that the Bears will continue to give Glennon every chance to start. But if Glennon doesn’t perform well, this will probably be his last opportunity to establish himself as more than just a backup, and he’ll probably end up as the backup for the rest of his career.
Since taking over as the team’s starting in 2009, Jay Cutler has only once led the Bears to the postseason due to his problems at the quarterback position. The Bears’ main offseason objective was to address the position, but it wasn’t apparent how they would do it—through free agency, trade, or the NFL draft.