Chicago Sports What Ifs: The 30 Biggest in Chicago History

Chicago Sports What Ifs: The 30 Biggest in Chicago 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. Over the last week, we've looked back 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.

Wednesday we moved to Soldier Field and examined the biggest "What if" players/scenarios in Bears history.

Thursday, we looked at the biggest "What if" players/scenarios in White Sox history.

Friday, we looked at the biggest "What if" players/scenarios in Cubs history.

Now, with a few additions to those five lists, let's rank the top 30 in Chicago history. For more details on the 25 from the individual team lists, click over and check out those specific articles.

30. What if the White Sox hadn't traded Aaron Roward for Jim Thome?

29. What if the Cubs hadn't drafted Shawon Dunston?

28. What if the Bulls had drafted ANYONE decent between 1991-98?

27. What if Jay Williams hadn't bought a motorcycle?

26. What if the White Sox hadn't waved the white flag in 1996?

25. What if the Bulls had developed a big man in the early 2000's?

24. What if Ronnie Fields hadn't crashed?

Ronnie Fields was a 6'2" guard on the Farrugut team that broke barriers when their center, Kevin Garnett, made the leap from Chicago prep hoops straight to the NBA. But if you watched the team play, or talked to opponents and scouts at the time, Garnett wasn't the best player on his own team. Fields was.

Fields was a three-time Parade All American selection (1994–96) and a consensus First Team All American (Parade, USA Today, McDonald's) his senior year. He was also the first sophomore ever to play in the "Best of the Best" game at the Nike All-American camp in 1993. Among the players involved in the 1992 game were Allen Iverson, Garnett, and Naismith Prep Player of the Year winner (and future Chicago Bull) Ron Mercer. But everyone wanted to see Fields.

Unfortunately, on Feb. 26, 1996, after signing a letter of intent to stay home in Chicago and play college ball at DePaul, Fields suffered a broken neck in an automobile accident. He never played a game in the NBA. If he hadn't been in that accident, what could Ronnie Fields have become at the pro level? And, if he had been eligible to attend DePaul, what would that team have looked like with Fields and future NBA players Quentin Richardson and Bobby Simmons?

23. What if the Blackhawks had traded Jeremy Roenick the first time?

22. What if the Hawks had chosen Hasek over Belfour?

21. What if Charlie Gardiner hadn't passed away?

20. What if the Sox had kept Sammy Sosa?

19. What if the commissioner hadn't banned Shoeless Joe Jackson?

18. What if Pat Fitzgerald hadn't broken a leg?
17. What if Brian Musso was ruled down?

Northwestern's magical run to the 1996 Rose Bowl qualifies for the list twice. The first "What if" every Wildcat fan asks regards their current head coach, Pat Fitzgerald. The star linebacker won both the Chuck Bednarik and the Bronko Nagurski Awards for his incredible performance during the 1995 season, but he broke his leg against Iowa with only one regular season game left on the calendar and wasn't able to play in the first Rose Bowl appearance for Northwestern since 1949 (1948 season).

In the game, the 10-1 Wildcats gave USC all they could handle. But in the second quarter, a controversial no-call may have given the Trojans just enough momentum to keep Northwestern from pulling off an upset of biblical proportions. Wide receiver Brian Musso caught a third down pass and it appeared his knee touched the ground before he fumbled the ball. The refs failed to blow the whistle, and Daylon McCutcheon scooped up the fumble and sprinted 53 yards for a touchdown. The play too the wind out of Northwestern's sails and gave USC a 17-point lead.

Northwestern battled back, but ultimately lost the game 41-32. Keyshawn Johnson, then a USC receiver who would become the number one overall pick in the NFL Draft, was named the game's MVP. I was at the game with more than 100,000 others, and was heart-broken when Musso didn't get a whistle; he graduated from the same high school I was attending at the time, and one of his younger brothers was in my brother's class.

If Gary Barnett and those Wildcats had pulled off the upset, what could they have become?

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

15. What if Mark Prior had stayed healthy?

14. What if Kerry Wood had stayed healthy?

13. What if Harry Caray had stayed on the South Side?

12. What if the Cubs had paid Greg Maddux?

11. What if Benji Wilson had lived on?

If Fields was a superstar, then Ben "Benji" Wilson was on a level prep hoops players didn't reach. In 1984, he was considered the best high school player in the country as a junior, and had the entire basketball world watching his every move. But an argument outside his high school, Simeon, ended with two bullets taking Wilson's life far too soon.

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

9. What if Gale Sayers had stayed healthy?

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

7. What if the Bulls had kept Olden Polynice?

6. What if the Cubs hadn't given up on Lou Brock?

5. What if Bobby Hull hadn't left the Blackhawks for the Jets?

4. What if the 1994 MLB Season had been completed (White Sox)?

3. What if the Bulls had called "heads" in 1979?

2. What if the Blackhawks didn't trade Phil Esposito?

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


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  • How many times did the Bears pass on Joe Montana in the draft? And Tom Brady was a 6th round pick for the Patriots. So, the Bears passed on him at least 5 times. Oh, and the Bears picked Cedric Benson in the 2005 NFL draft, while the Packers later picked some Cal quarterback named Aaron Rodgers

  • What if in 1980, the Bulls hadn't traded Clark Kellogg for Ronnie Lester and his injured knee?

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