From Tom Brady to Aaron Rodgers, the Bears passed over 9 of the 12 quarterbacks in the NFL playoffs

It has become an obligatory annual question for George McCaskey, with the Bears chairman asked to detail his mother's emotions regarding the state of the Bears. Virginia McCaskey will turn 97 on Sunday. And while George McCaskey didn't go so far this year as to paint his mom as "pissed off" with the team's struggles, he readily acknowledged that the citywide disappointment hit close to home.

With all the anticipation and hype that led up to the Bears' 100th season, the team's 8-8 fizzle-out was entirely unsatisfying.

"The hope was there. The Bears were back," George McCaskey said Tuesday morning. "And then to take a step back was especially disappointing. And she feels it, like all Bears fans do."

Ah, yes. That all-too-familiar feeling of deflation.

"Every year we talk about the goal being to win the Super Bowl," McCaskey said. "And in some years you feel you are better positioned to do that than others. We certainly thought that was the case in 2019. So the 8-8 record was especially disappointing in that light."

The playoffs will again go on without the Bears — for the 11th time in 13 seasons. And as if that sting weren't sharp enough, the emptiness surrounding the 2019 season will be amplified by another bit of "What might have been" lament.

This year's postseason includes nine starting quarterbacks the Bears once had a chance to draft but didn't. Yep. Seventy-five percent of the starting quarterback in this year's Super Bowl bracket could have begun their careers with the Bears if the organization had wanted them badly enough.

On that topic, here's a painful history lesson (in chronological order) of the draft-weekend decisions that took the Bears in a different direction.

Tom Brady, Patriots

A sixth-round draft pick in 2000, Tom Brady has led the Patriots to six Super Bowl titles -- and counting. (Adrian Kraus / AP)

Drafted: Sixth round (No. 199 overall) by the Patriots in 2000.

Player selected with the Bears' previous pick: K Paul Edinger (No. 174).

Other Bears selected before that in that draft: LB Brian Urlacher (No. 9), S Mike Brown (No. 39), WR Dez White (No. 69), TE Dustin Lyman (No. 87), CB Reggie Austin (No. 125), WR Frank Murphy (No. 170).

Bears incumbent starting quarterback: Cade McNown.

The knocks: Brady was thought of as a wiry quarterback with limited athleticism and average arm strength. He hadn't started his first two seasons at Michigan and even in his last two years, he continued competing for playing time with Drew Henson. Brady left college with 30 touchdown passes and 17 interceptions.

The scoop: Can you imagine if the Bears had a 2000 draft class that featured Urlacher and Brady? Can you even fathom, in retrospect, that the organization had seven chances to draft Brady and instead opted for players such as Frank Murphy? Obviously, no one in the spring of 2000 was projecting Brady to play for two decades and win six Super Bowls (and counting). And the Bears, for what it's worth, had taken their big swing at finding a franchise quarterback the previous year when they drafted Cade McNown at No. 12. But it's clear that too many teams failed to recognize or properly weight Brady's most special skills such as his competitiveness, savvy, accuracy and natural leadership ability. Interestingly, this fall in an article for The Athletic, longtime NFL writer Bob McGinn shared pre-draft notes on Brady that he compiled from five NFL executives, including Bill Rees, who at the time was the Bears director of college scouting. Rees' thumbnail on Brady: "Very accurate, good toughness, good leadership. Has a chance to be a good player in the league in time. I think he'd be a real solid backup initially and end up growing into a starter."

Drew Brees, Saints

Saints quarterback Drew Brees, throwing against the Panthers during a Dec. 29 game in Charlotte, N.C., is the all-time leader in passing yards, touchdown passes and completion percentage. (Streeter Lecka/Getty)

Drafted: Second round (No. 32) by the Chargers in 2001.

Player selected with the Bears' previous pick: WR David Terrell (No. 8).

Bears incumbent starting quarterback: Jim Miller.

The knocks: In scouting circles, Brees was most criticized for his lack of prototypical height (6 feet). Others thought his college production was inflated by the nature of Joe Tiller's spread offense at Purdue. Still, Brees received widespread praise for being a fiery competitor who shattered records at Purdue, became a Heisman Trophy finalist and led the Boilermakers to the Rose Bowl.

The lowdown: Brees was selected at the top of the second round and was the second quarterback off the board after Michael Vick was taken with the No. 1 pick. The Bears felt comfortable with their quarterback trio of Jim Miller, Shane Matthews and Cade McNown. (After Jerry Angelo became the general manager in June 2001, the team traded McNown to the Dolphins that same summer.) Brees, now in his 20th season, continues to rewrite the NFL record book. Terrell turned out to be a first-round flameout, finishing his four-season career with the Bears with 128 catches, 1,602 yards and nine touchdowns.

Aaron Rodgers, Packers

Packers quarterback Aaron Rodgers, throwing a pass against the Bears on Sept. 5 at Soldier Field, was the 24th pick in the 2005 draft. (Jose M. Osorio / Chicago Tribune)

Drafted: First round (No. 24) by the Packers in 2005.

Player selected with the Bears' previous pick: RB Cedric Benson (No. 4).

Bears incumbent starting quarterback: Rex Grossman.

The knocks: Rodgers' torturous wait in the NFL draft green room has been well-chronicled. Twenty-one teams passed him over, with the Vikings and Cowboys both making two picks while Rodgers was on the board. In some league circles, a large amount of Rodgers' college success was credited to the system of Cal coach Jeff Tedford. Rodgers was frequently compared to Joey Harrington and Kyle Boller, who also played under Tedford in college but failed to live up to expectations in the NFL.

The lowdown: Angelo was still firmly behind Grossman as his franchise quarterback, confident that the young gunslinger would return from the previous season's ACL injury to lead the Bears to new heights. Through that lens, it makes sense that the Bears wouldn't prioritize taking a quarterback in the top five of that draft, even with Angelo openly rating Rodgers ahead of Alex Smith as the top one in the class. But let's not forget: The Packers had Brett Favre as their starter when they picked Rodgers at No. 24. And it turned out to be a wise investment. In 12 years as the Packers starter, Rodgers has won six division titles, nine playoff games, two MVP awards and a Super Bowl. The other NFC North players drafted ahead of him: Benson, receivers Troy Williamson and Mike Williams and defensive end Erasmus James.

Russell Wilson, Seahawks

The Seahawks drafted quarterback Russell Wilson in the third round in 2012, arguably the best pick of the class. (Stephen Brashear / AP)

Drafted: Third round (No. 75 overall) by the Seahawks in 2012.

Player selected with the Bears' previous pick: WR Alshon Jeffery (No. 45).

Other Bears selected before that in that draft: DE Shea McClellin (No. 19).

Bears incumbent starting quarterback: Jay Cutler.

The knocks: Like Brees, Wilson's height (5-11) was deemed problematic. There were additional worries about his ability to be a traditional pocket passer in the NFL. Talent evaluators also wondered how Wilson's improvisational athleticism would translate against bigger, faster, stronger defenders.

The lowdown: Five quarterbacks came off the board before Wilson — Andrew Luck, Robert Griffin III, Ryan Tannehill, Brandon Weeden and Brock Osweiler. Two Wilsons also came off the board before Russell — running back David Wilson and safety Tavon Wilson. Needless to say, Wilson was easily the best value pick of the 2012 draft and probably tops Luke Kuechly and Harrison Smith as the top player of the class. The Bears had Cutler as their starter and had signed Jason Campbell as their backup a month before the draft. The opportunity to pick Wilson never matched up with their board.

Kirk Cousins, Vikings

Vikings quarterback Kirk Cousins throws a pass during against the Packers on Dec. 23 in Minneapolis. The Redskins selected Cousins in the fourth round in 2012. (Andy Clayton-King / AP)

Drafted: Fourth round (No. 102) by the Redskins in 2012.

Player selected with the Bears' previous pick: S Brandon Hardin.

Other Bears selected before that in that draft: McClellin, Jeffery.

Bears incumbent starting quarterback: Cutler.

The knocks: Cousins was thought to have a limited ceiling, projected by many as a career backup who excelled most as a game manager. He had ordinary athleticism. Very little on his scouting report stood out as elite.

The lowdown: Even though the Redskins pushed all their chips to the center of the table to draft Robert Griffin III at No. 2, they dipped back into the 2012 quarterback class the next night to grab Cousins in Round 4. The team wanted to add depth and stabilize the position with a young, talented quarterback they could groom. Eventually, when Griffin's career went off the rails, Cousins took over. It's worth noting that the Seahawks and Redskins hit on midround quarterbacks in 2012. With Wilson, the Seahawks found a catalyst to start a nine-season run that has seen them win 86 regular-season games while making seven playoff appearances. Four picks later, the Bears drafted Hardin, who suffered a series of injuries and never played a regular-season game.

Jimmy Garoppolo, Patriots

49ers quarterback Jimmy Garoppolo makes a throw against the Seahawks on Sunday in Seattle. He was a second-round pick by the Patriots in 2014. (Ted S. Warren/AP)

Drafted: Second round (No. 62) by the Patriots in 2014.

Player selected with the Bears' previous pick: DT Ego Ferguson (No. 51).

Other Bears selected before that in that draft: CB Kyle Fuller (No. 14).

Bears incumbent starting quarterback: Cutler.

The knocks: Coming out of the Ohio Valley Conference in the Football Championship Subdivision, there were questions as to how to translate Garoppolo's impressive statistical production, which included 5,050 passing yards, 53 touchdowns and only nine interceptions his senior year at Eastern Illinois. There also were criticisms of his deep-ball production and ability to operate from under center after playing his college career exclusively out of the shotgun.

The lowdown: Before the draft, Emery had privately expressed praise for Garoppolo's quick release, accuracy and feel for the game. But it wasn't enough to convince the Bears to use a second-round pick on the up-and-coming quarterback from Arlington Heights. In retrospect, the choice of Ferguson stings even more. Three months before the draft, the Bears had given Cutler his massive seven-year, $126 million extension. They later chose to fill their backup position with a different Jimmy, signing free agent Jimmy Clausen in June.

Patrick Mahomes, Chiefs

Chiefs quarterback Patrick Mahomes runs the ball in for a touchdown against the Bears at on Dec. 22 at Soldier Field. Mahomes was the 10th pick in the 2017 draft, eight spots after the Bears selected Mitch Trubisky. (Armando L. Sanchez / Chicago Tribune)

Drafted: First round (No. 10) by the Chiefs in 2017.

Player selected with the Bears' previous pick: QB Mitch Trubisky (No. 2).

Bears incumbent starting quarterback: Mike Glennon.

The knocks: Mahomes was criticized for improvising too frequently and becoming too much of a risk taker whose desire to hit the big play created a habit of frequently throwing the ball into coverage and hoping for the best. That, draft experts and talent evaluators warned, could prove problematic in the NFL. Mahomes' prolific stats also were seen as inflated by the pass-happy offense he played in at Texas Tech.

The lowdown: The Bears were in the market for a quarterback. Ryan Pace was intent on drafting one and had Mahomes in the top cloud on the team's draft board. Pace was enamored with Mahomes' big arm and big-play ability. But he had become even more impressed with Trubisky, believing he had better accuracy, footwork and pocket presence. The belief for Pace was that, even with Trubisky making only 13 starts at North Carolina, his skill set would eventually distinguish him as the quarterback in the class most equipped for high-level success. At the end of Trubisky's third season, however, the gap has widened significantly between him and Mahomes. Mahomes won last year's NFL MVP award and has the Chiefs again positioned for a potential deep playoff run.

Deshaun Watson, Texans

Texans quarterback Deshaun Watson warms up before a game against the Titans on Sunday. He was the 12th pick in the 2017 draft. (Eric Christian Smith/AP)

Drafted: First round (No. 12) by the Texans in 2017.

Player selected with the Bears' previous pick: Trubisky.

Bears incumbent starting quarterback: Glennon.

The knocks: Watson's 32 career interceptions at Clemson were seen as a red flag. There were additional questions about his slender frame and ability to hold up physically against NFL defenders. Some scouts were uncertain how quickly Watson would be able to handle the mountain of pre-snap responsibilities NFL quarterbacks face.

The lowdown: For reasons that have still never been divulged publicly, Pace and Bears director of player personnel Josh Lucas didn't believe Watson was on the same tier as Trubisky or Mahomes even though then-coach John Fox and quarterbacks coach Dave Ragone rated Watson as their No. 1 quarterback in the class. The Bears interviewed Watson at the combine and spent additional time with him after his pro day at Clemson. But they did not take him out to dinner or put him through a private workout as they did with the other two top quarterbacks in the class. It was a miscalculation on multiple levels, particularly with Watson's special leadership skills and performance in leading Clemson to back-to-back national championship games and the 2016 title.

Lamar Jackson, Ravens

Ravens quarterback Lamar Jackson, looking to throw against the Browns on Dec. 22, was the 32nd pick in the 2018 draft. (Joshua Gunter / TNS)

Drafted: First round (No. 32) by the Ravens in 2018.

Player selected with the Bears' previous pick: LB Roquan Smith (No. 8).

Bears incumbent starting quarterback: Trubisky.

The knocks: Jackson was polarizing as he entered the 2018 draft. His harshest critics skewered his ability as a pocket passer and questioned whether his special running prowess would leave him vulnerable to injury in the NFL. He was labeled as a bit too short and perhaps a bit too skinny to survive at the next level. His throwing accuracy was seen as erratic.

The lowdown: No one was pining for the Bears to take Jackson when the 2018 draft arrived, particularly not in the top 10. And no one anywhere projected Jackson to become an MVP front-runner by the end of his second season. Still, the Ravens deserve credit for identifying Jackson's greatest game-changing strengths and working to bring those out as often as possible. Their ability to develop the offense and the young quarterback in unison has helped make them the favorite to win this year's Super Bowl.

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