Barring any last-minute surprises, the Chicago Bears’ 2020 offseason has concluded when it comes to their signings, releases, and draft selections. General manager Ryan Pace has arguably had his busiest offseason, bringing in numerous veterans via free agency and trades while maneuvering through the 2020 NFL Draft to find the most impactful players.
But when it comes to the holdovers on the roster, who benefited from the moves and who didn’t?
Read on to see the list of winners and losers this offseason.
Winner: OLB Khalil Mack

Last season didn’t go as planned for Khalil Mack. Following an All-Pro season in 2018 where he sprinted out of the gates to torment opposing quarterbacks, Mack was relatively quiet in 2019. He still had 8.5 sacks and five forced fumbles, but he wasn’t able to change games like he had during the previous season. Perhaps it was due to the lack of production on the other side?
Enter outside linebacker Robert Quinn, one of the best pure edge rushers in the league. Quinn, who had 11.5 sacks for the Dallas Cowboys last season, signed a five-year, $70 million deal this offseason and replaces the ineffective Leonard Floyd. He immediately provides a boost on the opposite end of of the defensive line and should draw more attention than Floyd ever did, allowing Mack to return to dominating offensive tackles.
Loser: QB Mitchell Trubisky

Mitchell Trubisky is easily the biggest loser of the offseason for the Bears. Pace made it a point to find competition at the position and he did so by trading a fourth-round pick for Nick Foles. Not only did the Bears seek out a veteran, they traded draft capital to find one. Whether Trubisky wins the quarterback competition or not, it’s clearly a vote of no confidence in the former second overall pick.
What’s worse, the Bears chose not to pick up Trubisky’s fifth-year option, making him a free agent next offseason. Whether this is truly Trubisky’s final year in Chicago remains to be seen. But his back is up against the wall and he’ll need to fight hard to come out on top.
Winner: OTs Charles Leno Jr. and Bobby Massie

One of the weakest links of the 2019 Bears was the offensive line, specifically their tackles. After a Pro-Bowl (alternate) season, Charles Leno Jr. struggled with penalties last year and regressed in terms of production. Bobby Massie had a disastrous season, ultimately finishing on injured reserve. Both players have a significant amount of money still owed to them over the next couple of seasons, but questions arose as to whether the team would bring in competition to push either starter.
While the Bears did sign offensive tackle Jason Spriggs and drafted a couple of offensive linemen in the seventh round of the 2020 NFL Draft (Arlington Hambright and Lachavious Simmons, respectively), none are expected to compete for a starting spot. Barring a surprise, Leno and Massie appear to be safe to start the season.
Loser: WR Javon Wims

Javon Wims proved me wrong last year when I named him one of the losers of the offseason. He saw more playing time but struggled at times with drops and penalties. Still, he solidified his spot as the team’s WR4 in 2019. But this year, the Bears brought in more receiver competition and Wims will once again be battling for a roster spot.
The former Georgia Bulldog will be competing with players like Ted Ginn Jr., Darnell Mooney, Trevor Davis, and Riley Ridley. Can Wims produce another standout performance during training camp? Or is he the odd man out? Either way, he faces an uphill battle when the preseason begins.
Winner: S Eddie Jackson

Eddie Jackson was one of many players who regressed last year after a stellar 2018 campaign, but it wasn’t necessarily his fault. The team brought in veteran safety Ha Ha Clinton-Dix, who essentially took over the free safety spot and moved Jackson to more of a strong safety, taking him out of his preferred position. While he didn’t have a bad season, it was a far cry from his All-Pro performance.
Clinton-Dix ended up signing with the Dallas Cowboys and the Bears signed veteran safety Tashaun Gipson, who last played with the Houston Texans. Gipson will play the strong safety role, allowing Jackson to return to free safety and resume his ball hawking tendencies. Jackson also signed a lucrative contract extension back in February so he’s arguably had the best offseason of any Bears player.
Loser: CB Kevin Toliver II

When the Bears released veteran cornerback Prince Amukamara back in February, Kevin Toliver viewed as the first player in line to take over the starting spot. Since then, however, the cornerback position has filled up with competition. The team signed Artie Burns and drafted Jaylon Johnson and Kindle Vildor. They join Toliver and Tre Roberson, who was also signed earlier this offseason.
Johnson, selected in the second round, may now have in the inside track to start opposite Pro-Bowl CB Kyle Fuller, with Toliver relegated to a reserve role yet again. The competition will begin when the pads come on later this summer, but Toliver faces an uphill battle.
Winner: WR Anthony Miller

Even though Anthony Miller is spending another offseason recovering from shoulder surgery, the arrow is pointing up for the third-year receiver. The Bears released receiver Taylor Gabriel earlier this year, paving the way for Miller to become the undisputed WR2, behind Allen Robinson. The team also worked to rectify its issues at tight end by bringing in Jimmy Graham and drafting Cole Kmet, while adding speedy receivers Darnell Mooney and Ted Ginn Jr.
Those acquisitions should open up the field more for Miller, allowing him to pick up where he left off after emerging during the second half of the season. In his final seven games, Miller totaled 35 catches for 438 yards and two touchdowns. He’s a popular breakout candidate for 2020 and assuming he fully recovers from his surgery, the Bears offseason has set him up for success, no matter who the quarterback ends up being.
Loser: Nearly every tight end

The Bears tight end position has become a punchline for many fans, given lack of production in 2019 and the fact the team still has nine players on their roster. Aside from Graham, Kmet and Demetrius Harris, who was signed earlier this year, every holdover from the 2019 season is on the hot seat. Trey Burton and Dax Raymond have already been cut and more will be on the way once the preseason gets underway.
Former second-round pick Adam Shaheen is likely first on the chopping block, given his ineffectiveness and inability to stay healthy following a promising rookie year in 2017. Other players such as J.P. Holtz, Jesper Horsted, Eric Saubert, Ben Braunecker and Darion Clark will all be fighting for spots on the team, but the odds are obviously stacked against them.