During the flurry of signings at the start of free agency, an unsurprising move fell under the radar. Jay Cutler, after missing most of the 2016 season with a labrum injury in his throwing shoulder, was released by the Chicago Bears.

The reception of the news among Bears fans was much like that of Eddie Lacy’s departure from Green Bay, good riddance. The expectations were high for Cutler, who despite leaving Chicago as their all-time passing touchdowns and passing yards leader, has been looked on widely as a disappointment for his 109 interceptions in eight seasons. His 2-11 record against Green Bay in games started in the regular season and playoffs was a cause of much frustration among Bears fans.

Just north of Chicago in the land of cheese however, Cutler will be remembered as the cause of side-splitting laughter and eye-rolling when our friends below the border tried to convince us he was elite. Cutler threw 23 interceptions in 13 games against the Packers while with Chicago. As Charles Woodson once said while with the Packers, “We don’t need luck; Jay will throw us the ball.”

Here they are, ranked by importance of the game, time in that game and how awful the throw or decision was that led to that pick.

23. Derrick Martin, First Quarter, Week 3 of 2010

Every interception except this one came in a game the Packers would ultimately win, so Martin’s pick of an overthrown Cutler pass to Greg Olsen in the end zone falls mostly for this reason. The Bears would win this game 20-17, helping set the stage for a dramatic season finale in Green Bay that season.

22. Nick Collins, First Quarter, Week 1 of 2009

This may have been the moment Bears fans began to question the Jay Cutler trade. Just over ten minutes into his first game with Chicago, Cutler rolled out of the pocket and threw a dart into double coverage that was off target and straight to Collins. This drive was deep in Packer territory, spoiling Cutler’s first potential scoring drive with Chicago. As they say on SportsCenter’s Top Ten plays, more from this game later…

21. Clay Matthews, Third Quarter, Week 4 of 2014

The Bears trailed 24-17 midway through the third quarter in a game where they had the chance to sink the Packers to 1-3 with a victory. Just outside the red zone, a short pass to Josh Morgan was broken on by Tramon Williams and deflected into the air, right to a waiting Clay Matthews near the line of scrimmage. Matthews nearly returned the pick for a touchdown, but pulled up due to a lingering hamstring injury. The ensuing drive led to a Jordy Nelson touchdown, bringing the game to 31-17 as the Packers began to pull away. Was this pick Cutler’s fault? Probably not. Was it funny? Absolutely.

20. Charles Woodson, First Quarter, Week 13 of 2009

This pick is very emblematic of the Cutler era as a whole: lofty expectations that ultimately fell well short. This time it was Woodson settling beneath the under-thrown pass intended for Devin Aromashodu. Woodson returned the pass for nine yards, leading to a Packers field goal. This was the first of two for Cutler in this game.

19. Morgan Burnett, First Quarter, Week 3 of 2011

Looking to answer an early Packers score, Cutler took a shot to Roy Williams, who had a step on the underneath coverage of Tramon Williams down the sideline. The pass hung in the air too long however, and Burnett was able to close for the interception, his first of two off Cutler in that game.

18. Jerron McMillian, Fourth Quarter, Week 2 of 2012

It is really a wonder why the Bears kept Cutler in for some of these games, but alas with three minutes left and the Bears trailing 23-10 with no timeouts remaining, he was still out there slinging picks. This time, a stare-down of his intended receiver Earl Bennett resulted in the fourth and final interception of Cutler’s second such game in Green Bay. The Bears would lose by the same score of 23-10.

17. Micah Hyde, First Quarter, Week 10 of 2014

This was actually a decent throw by Cutler. He was looking for Martellus Bennett on an out route to the sideline, and delivered a high pass where seemingly only Bennett could catch it. It was not quite high enough however, and hung just long enough for Hyde to knife underneath and pick it off. The pick set Green Bay up nicely at the Bears 23 yard line, and they would score four plays later to increase their lead to 14-0.

16. Tramon Williams, Second Quarter, Week 2 of 2012

Cutler, facing a blitz on second down as he tried to lead his team back from a 10-0 hole before halftime, tried to squeeze a pass to Earl Bennett over the middle. Williams dove in front for his first of two interceptions in the game. It was also the first of four picks for Cutler, who was having nightmares of 2009 all over again.

15. Charles Woodson, Third Quarter, Week 2 of 2012

Cutler dug his trailing Bears in a deeper hole while trailing 13-3 late in the third quarter, scrambling out of the pocket to cork a heater over the middle to Earl Bennett. Woodson was all over it like a meatball pitch in the Packers’ charity softball game. This was Cutler’s second of four in the game, and Woodson’s 55th pick of his career.

14. Tramon Williams, Second Quarter, Week 1 of 2009

Only two minutes of game time after throwing his second pick with Chicago, Cutler faced third and eight and a heavy blitz from a pair of Packers rushers. Apparently not knowing the meaning of “throw the ball away,” Cutler chucked a reckless pass over the middle, which NBC cameras could not even capture the intended receiver of before it was picked by Williams, who returned the pass from his own 35 down to the three yard line of Chicago. This capped a scoreless first half for the Bears offense, with a safety by the defense saving them from a bagel.

13. Casey Hayward, Second Quarter, Week 14 of 2012

Cutler made one too many mistakes in a close game by squandering a late first-half opportunity with a horrendous throw over the middle to Hayward. The pass, intended for Devin Hester, appeared to be a case of receiver breaking one way, defender breaking another, with Cutler getting confused and throwing it right to Hayward. The then-rookie returned his sixth pick into Bears territory for a 28 yard return that led to a late first-half Packers touchdown. The Packers would go on to win 21-13.

12. Tramon Williams, Fourth Quarter, Week 2 of 2012

Now trailing 16-3 in part thanks to Cutler’s inability to hang on to the ball while conducting the Bears offense, he was once again in fourth quarter panic mode. A deep heave to Brandon Marshall in double coverage was under-thrown, tipped and caught by Williams for his second and Cutler’s third of the game. Under-thrown and double coverage are starting to become key words here…

11. Nick Collins, Fourth Quarter, Week 13 of 2009

With the Bears leading at the start of the fourth quarter 14-13, Cutler had a chance to drive the Bears down for an insurance score. Instead, on a third and five from his own 32, Cutler panicked in the face of a blitz and rushed a pass to the left side. In what was either a miscommunication, a really poor route by Knox or a combination of both, the pass fell into the waiting arms of Collins as Knox stumbled nearly five yards behind. Collins returned the pick inside the Bears’ 20 yard line, leading to a touchdown and two-point conversion that would prove to be the difference in a 21-14 Packers victory.

10. Casey Hayward, Fourth Quarter, Week 10 of 2014

Another unfortunate deflection led to the only pick-six on this long list of futility. Trailing 48-7 in another head-scratching “why was he out there?” moment, Cutler was trying to save a shred of dignity in the game by driving the Bears down for a second score with just under 11 minutes to play. His throw careened of the helmet of his lineman Kyle Long, into the hands of Hayward, who ran 82 yards for the score. Green Bay won 55-14, starting a run of seven of their final eight games en route to a first round bye in the playoffs.

9. Sam Shields, Third Quarter, Week 4 of 2014

Trailing 31-17 in what was once a close game, Cutler began to unravel. On the very next possession after an unfortunate bounce led to his first interception, Cutler threw an inexplicable pass right to Sam Shields. The receiver ran downfield, Shields kept his eyes on Cutler and was caught underneath. A good throw might have led to a score, but instead Cutler threw a bullet to Shields, who returned it 62 yards to the Bears ten yard line. A game that was once 24-17 became 38-17 in half a quarter due to errant throws from Cutler.

8. Morgan Burnett, Fourth Quarter, Week 3 of 2011

With the Packers leading 27-10 in the fourth quarter with 12 minutes left, Cutler was trying desperately to get his team back in the game. As we know, Cutler and desperation throws rarely end well for him, and although Roy Williams again had a step on Tramon Williams, the pass was behind his target and picked by Burnett. This stalled drive helped the Packers secure a 27-17 victory to improve to 3-0 in a season they would start 13-0.

7. Clay Matthews, Fourth Quarter, Week 1 of 2015

The final Green Bay interception off of Cutler during his time with the Bears was another game clincher for the Packers. Green Bay led 24-16 with Chicago driving just outside the red zone. Cutler, overlooking Clay Matthews in a zone assignment over the middle, fired a pass to Martellus Bennett that Matthews undercut. Matthews returned the pass 48 yards, 15 of which were cut off on an illegal block in the back on the return. The Packers would capitalize with an Eddie Lacy touchdown run, giving them enough distance to hold off the Bears 31-23.

6. Al Harris, Fourth Quarter, Week 1 of 2009

In what was a fitting conclusion to a miserable start of the Cutler era, a final comeback attempt with about a minute remaining was cut short by a crafty Harris. Intended receiver Johnny Knox slipped, or was knocked slightly off his route by Harris’ bump and run coverage. Harris read Knox’s route, and stepped in front of Cutler’s secondary read for a game-clinching interception that was nearly returned for a touchdown. Two of Cutler’s four interceptions from this game came within ten yards of being returned for touchdowns.

5. Charlie Peprah, Third Quarter, Week 17 of 2010

On third and 19 midway through the third quarter of a must-win contest for the Packers, Cutler presented the first of two late Christmas gifts to Packers defenders. Trying to thread the needle between double coverage to Knox in the end zone, Peprah leaped in front of the pass to save a touchdown in a low-scoring 3-0 game at the time in favor of the Bears. The turnover kept the game in reach for a Packers team fighting to make the playoffs.

4. Johnny Jolly, Second Quarter, Week 1 of 2009

The second of Cutler’s four-pick debut was possibly his most pathetic pick thrown against the Packers. If he, not Caleb Hanie, had thrown the pick-six to B.J. Raji in the NFC Championship, that would take the cake. However, this was Cutler’s only throw to a Green Bay defensive tackle, which came on an attempted third and goal screen pass to Matt Forte. Somehow, Cutler could not see the 6’3″ 320 pound (listed weight) Jolly, and threw it right to him. The Packers would win this game 21-15, most certainly as a direct result of Cutler’s turnovers. This one is ranked so highly out of the sheer impossibility of the throw.

3. Sam Shields, Fourth Quarter, Week 17 of 2013

To be fair to Cutler, this game was relatively well-played by him, and it was more due to a brilliantly blown coverage by Chris Conte that the Bears lost. Cutler even had his best career QB rating against Green Bay of 103.8 in this game. With ten seconds left after Rodgers and Randall Cobb connected for a 48 yard go-ahead score, Cutler had one last chance to win the Bears the division from 45 yards out with a Hail Mary to Brandon Marshall. Heaving a prayer across his body into double coverage, the pass came up short and was intercepted by Shields. The Packers won 33-28, clinching the division for Green Bay despite Rodgers missing nine games with a broken collar bone.

2. Sam Shields, Second Quarter, NFC Championship 2011

Just off the heels of an Aaron Rodgers interception thrown to Lance Briggs, it appeared the Bears had something going with 42 seconds, two timeouts and the ball at Green Bay’s 41 yard line. Feeling confident, Cutler took a shot in one on one coverage to Knox against rookie corner Sam Shields to the end zone. Shields high-pointed the pass and stole an important scoring opportunity from Chicago in a close 21-14 victory. Cutler eventually gave way to Caleb Hanie due to injury, who threw the infamous Raji pick-six that all but clinched a Super Bowl berth.

1. Nick Collins, Fourth Quarter, Week 17 of 2010

From the Packers 32 yard line with 20 seconds and a timeout to burn, Cutler had the Bears within striking distance of a game-tying touchdown that could have helped end the Packers’ Super Bowl run before it started in overtime. Instead, an overthrown pass intended for Devin Hester was intercepted by Nick Collins, securing a playoff berth for Green Bay in a 10-3 win that would ultimately lead to a Super Bowl XLV victory. Of all of Cutler’s ill-timed, off-target throws, this one had the greatest impact on the history of these two franchises.

To watch all of these picks in one nine minute compilation, click here.

Which Cutler pick will you always remember? Which were ranked too high/low on my list? Let me know in the comments.