Chicago Sports What Ifs: The 5 Biggest in Cubs History

Chicago Sports What Ifs: The 5 Biggest in Cubs 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.

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.

Now, let's head to the North Side and look back at the biggest "What if" players/scenarios in the history of the Cubs. Where will Woody rank?

Honorable Mention: What if the Cubs had kept Josh Hamilton?

On Dec. 7, 2006, that winter's Rule V Draft took place. The Cubs received cash from the Reds, and selected "once-promising" but "troubled" outfield prospect Josh Hamilton out of the Tampa Bay Rays organization. Looking back at the 2007 Cubs, when Alfonso Soriano hit 33 home runs and Aramis Ramirez knocked in 101 runs while both of them missed around 30 games, the potential of that roster with Hamilton in it at least makes the mind wander.. The Cubs won the NL Central by two games (85-77), but (of course) didn't do anything in the playoffs. What if Hamilton, who hit 19 home runs in 90 games for the Reds, had taken the place of Cliff Floyd or Jacque Jones on that team?

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

The Cubs had the number one overall pick in the 1982 draft and used it on Dunston, a shortstop from Thomas Jefferson High School in Brooklyn, NY. He went on to inspire the iconic Shawon-O-Meter and was loved by the fans at Wrigley Field. In his career, he played in over 1,800 major league games.

But another high school kid could have been picked by the Cubs that year. This one, a pitcher from Hillsborough High School in Tampa, FL, exploded onto the scene a couple years later. What if the Cubs had taken Dwight Gooden instead of Dunston in 1982? We'll never know.

[Note: now-Cubs manager Dale Sveum was the 25th overall selection in that same draft.]

4. What if Mark Prior stayed healthy?

Another high draft pick that failed, Cubs fans (and most scouts) thought the Minnesota Twins did Chicago a favor by drafting local high school catcher Joe Mauer instead of college pitching god Mark Prior out of USC. The Cubs willingly selected Prior, paid him what he wanted, and ran him to the top of their rotation where he and Kerry Wood were supposed to take the Cubs to the promised land. And, in 2003, they almost did it. Today, he's throwing in the minors for the Boston Red Sox and his #22 has become a niche nostalgia jersey for 30-somethings all over Chicago.

3. What if Kerry Wood had stayed healthy?

We can argue all day about who killed Wood's arm. His high school coach pitched him in both halves of a double header. Dusty Baker kept running him out there even when he was hurting. And he ignored the pleas of coaches and idiots in the press box to correct his mechanics to avoid the issues that ultimately cut his promising career as a starter short.

But nobody can deny that, when he came up, there wasn't a guy in baseball with the stuff he had. His 20-strikeout game is legend for more reasons than drunken Cubs fans remembering "glory days," and his comeback from injury to dominate in 2003 was striking.

2. What if the Cubs had paid Greg Maddux?

Maddux won his first Cy Young Award with the Cubs, and then went to Atlanta and built arguably the most impressive resume for a non-power pitcher in history. He's a first ballot Hall of Famer, but put up the best numbers of his great career in a Braves uniform. The 1990s in Chicago became a soiled mess of a rebuilding project until Wood, Prior and Zambrano arrived on the scene. But most Cubs fans over the age of 30 will forever wonder what if the Cubs had given Maddux what he wanted.

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

Ernie Broglio won 18 games, pitched 11 complete games and five shutouts in 1963 for the St. Louis Cardinals. In just over five seasons in St. Louis, Broglio had won 70 games and had thrown 18 shutouts, peaking with 21 wins and a third place finish in the Cy Young vote in 1960.

So when the Cubs traded an underwhelming young outfielder for him in June of 1964, it shouldn't have seemed like a terrible move.

In 1963, Lou Brock had 141 hits and 122 strikeouts for the Cubs. Brock had played 327 games for the Cubs before he was traded (within just days of his 25th birthday), and had a mediocre .306 on-base percentage. Indeed, he had only stolen 50 games for the Cubs, and their veteran lineup needed someone to help the pitching staff more than a kid that looked like a project.

After the trade, Brock stole 888 bases in St. Louis and was the best base stealing threat before Rickey Henderson in big league history. He built a Hall of Fame career that included a .347 on-base percentage and over 1,400 runs scored. Broglio was damaged goods, suffering from arm issues and winning only seven of 26 decisions in pieces of three seasons with the Cubs before walking away from the game.

This remains one of the worst trades in the history of any professional sport, and is without question the greatest "What if" in Cubs history.

For more incredible stories from the history of the Cubs, check out Jimmy Greenfield's book: 100 Things Cubs Fans Should Know & Do Before They Die

We're going to bring this series to a close with the top 30 "What if" players/scenarios in Chicago history this weekend, ranking those from the five teams and adding a few that didn't involve those teams as well.

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