Glennon, 27, played in 19 games for the Tampa Bay Buccaneers from 2013-14, throwing for 4,025 yards, 29 touchdowns and 15 interceptions. The 6-foot-6 quarterback has appeared in just two games since Tampa drafted Jameis Winston No. 1 overall in 2015.
Terms: Three-years, $45 million with $19 million guaranteed, per ESPN NFL Insider Adam Schefter
ESPN 150 ranking: 41
Grade: Hard to go higher than B-minus. On one hand, Glennon's immediate potential is greater than the other available free-agent quarterbacks -- minus Tony Romo. Plus, the Bucs' front office and coaching staff liked Glennon enough to offer him the league's richest backup quarterback contract. Glennon arrives in Chicago with an excellent reputation, but he hasn't started a game in two years. No one truly knows what his floor is -- unlike the experienced and thoroughly scouted Brian Hoyer, who is poised to join the San Francisco 49ers. This move requires a leap of faith from a franchise that's 9-23 over the past two seasons.
What it means: A changing of the guard in Chicago after eight mostly disappointing seasons with Jay Cutler atop the depth chart. Glennon has the opportunity to keep the Bears job beyond 2017, but Chicago must still draft a quarterback. Glennon's salary puts him in the lower tier of starters. So the Bears aren't ready to anoint him their savior, but he's the guy until further notice. It's difficult to envision a rookie unseating him in Year 1. Still, signing Glennon -- the Bears essentially bid against themselves for his services -- is general manager Ryan Pace's biggest roll of the dice to date. This could be the defining moment, positive or negative, of his tenure in Chicago.
What's the risk: How much time do you have? Again, Glennon hasn't been a starter since 2014. That's worrisome. Strictly a pocket passer, Glennon is known to have a strong arm and can push the ball downfield, but mobility is an issue. Also, Glennon isn't exactly surrounded by the best group of receivers. That will be another challenge. The Bears have to be careful not to handcuff themselves to Glennon for too long. The last thing Chicago needs is its version of Brock Osweiler. However, the Bears guaranteed Glennon far less than the Houston Texans did Osweiler ($37 million). That's a good thing, because in the event Glennon falters -- or the to-be-determined rookie develops sooner and better than expected -- the Bears have to be ready to cut the cord.