Chicago Sports What Ifs: The 5 Biggest in Bears History

Chicago Sports What Ifs: The 5 Biggest in Bears History

In the wake of Kerry Wood announcing his retirement from the Chicago Cubs, fans have engaged in a number of discussions surrounding Chicago sports. Wood certainly left a lot of fans wondering what could have been had he stayed healthy, but Wood isn't the greatest "What if" player in Chicago. In fact, there are a number of players and scenarios that have made fans ask that multi-million dollar question over the years.

In the coming days, we're going to look at the biggest "What if" players and scenarios in each Chicago team's history. Monday, we looked back at the five biggest "What if" players/scenarios in Blackhawks history. Tuesday, we crossed the United Center locker rooms to look at the biggest "What if" players/scenarios in Bulls history.

Now, let's look at the five biggest "What if" players/scenarios in the history of the Bears.

Honorable Mention: What if Doug Flutie was taller?

Maybe Skee-Lo was thinking of Flutie? He won a Heisman Trophy at Boston College in 1984, which was good enough to make him the... 285th overall selection of the 1985 NFL Draft by the Los Angeles Rams. In the 11th round. Why did he last that long in the draft after such a great college career? He was listed (generously) at 5'10" and 180 pounds.

The Bears acquired him in a trade the following year to back up Jim McMahon as they defended their Super Bowl title. When McMahon got hurt, Da Coach made a great deal of people's eyebrows dance when he started Flutie in the final game of the regular season and the playoff game against the Washington Redskins (that the Bears lost). He was then traded to the New England Patriots during the strike in 1987. After nine great years in Canada, he returned and had a few good seasons with the Buffalo Bills, San Diego Chargers and a career finale with the Pats as a 43-year-old.

But if Flutie hadn't been deemed too small to play quarterback in the NFL, would the Bears have handed him the reigns as McMahon's injury issues grew?

5. What if the Bears had a clue when it came to drafting quarterbacks?

A lot has been said about the number of starting quarterbacks the Bears used while Brett Favre was the man in Green Bay (cliff notes: they made 42 quarterback changes while Favre didn't miss a game). But looking back through the Bears' draft history is even worse than looking back through the list of starters. Erik Kramer, the one bright spot in the last 20 years, was brought in as a free agent. With all due respect to Kyle Orton and Rex Grossman, the last time the Bears drafted a bona fide NFL quarterback was when they selected Jim Harbaugh out of Michigan in 1987.

Here's some sickening perspective: on the Chicago Bears website's official active roster, 45 players were born after the team selected Harbaugh in 1987. Think about that for a moment. Jay Cutler was four years old when Harbaugh move from Ann Arbor to Chicago. What if the Bears had drafted a winner once... just once...?

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4. What if Walter Payton had played on good Bears teams his entire career?

When Emmitt Smith was inducted into the Pro Football Hall of Fame in 2010, I wrote an extensive piece describing what made Walter Payton the greatest running back in the history of the game. He didn't have a Pro Bowl player on the offensive line in front of him and didn't play on a winning team until the final few seasons of his career, but he still broke the all-time rushing record and was the best all-around threat at the position in the game. If he had played behind a dominant line, how many more yards would Sweetness accumulated in his incredible career?

3. What if Gale Sayers had been able to stay healthy?

For younger football fans, try to wrap your brain around this idea: a hybrid of Devin Hester and Matt Forte. Sayers was known as "the Kansas Comet" when the Bears made him the fourth overall pick in 1965, completing the greatest draft class for any NFL franchise in history (they also selected Dick Butkus in that draft). Sayers is still the NFL's all-time leader in average yards per kick return (30.6), and once scored six touchdowns in a game. He was the fastest player in the league, and one of the best running backs as well as the most dynamic returner in the game.

But in 1968 he suffered a horrific injury to his right knee. He returned to lead the NFL in rushing the following season despite the Bears being a last place team, but blew his left knee out in 1970. If he had stayed healthy, what kind of numbers would he have ultimately put up? Consider he had 9,435 all-purpose yards in only 68 games played (138.8 per game). Compare that to Walter Payton, who 21,803 all-purpose yards in 190 career games (114.8 per game). Sayers' has the shortest resume in the Pro Football Hall of Fame, but he was good enough to merit induction in spite of his injuries. In 1999, almost 30 years after his brief career ended, "The Sporting News" still ranked him 22nd on their list of the 100 greatest players in NFL history.

And, of course, if he hadn't been injured there wouldn't have been "Brian's Song."

2. What if Charles Martin hadn't body slammed The Punky QB in 1986?

I guess the follow-up question would be how long would Roger Goodell suspend Martin for this hit today? He was suspended for two games for ending McMahon's season. The 1986 Bears were, at least on paper, as good as the 1985 team in many ways. But this filthy hit by Martin was a game-changer and effectively ended not only the Bears' hopes of a repeat as Super Bowl champions, but impacted the rest of McMahon's career.

McMahon was a brilliant quarterback, winning 21 straight regular season starts for Chicago and finishing his career with a 67-30 record as a starting quarterback. But he proved to be fragile and, after Martin's hit, was never the same. If he had been able to stay in the game, where could those Bears have gone?

1. What if Buddy Ryan and Mike Ditka got along?

Perhaps the fact that they didn't get along was what made the teams of the early 1980s so special. But their fractured relationship ultimately ran the loved defensive coordinator out of town after the Super Bowl. One of the most striking images from that great victory was the Bears' players carrying two coaches off the field after the win. The offense carried Ditka off, while the defense carried Ryan.

Ryan never won a championship as a head coach, and Ditka didn't win another after Ryan left. While they were together, in spite of their hate for each other, they led some incredible teams that had some of the great personalities of their era in the NFL.

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