Chicago Cubs: What if these five things never happened in Cubs history?

Chicago Cubs: What if the team had re-signed Greg Maddux?

Few things in Chicago Cubs history have stung more than letting Greg Maddux getaway. Arguably the greatest pitcher of his generation, Maddux came up with the Cubs in 1986 and, after struggling for a couple of years, put it all together starting in 1988. For the next five years, he started 176 games for the Cubs and won 87 games with a 3.01 ERA, culminating in winning the NL Cy Young Award in 1992.

Maddux departed for the Atlanta Braves and proceeded to win three more Cy Young Awards in a row while placing in the top five four additional times. Cubs general manager Larry Himes, though he got high marks for trading for Sammy Sosa, has been blamed for letting Maddux go. What if Maddux had stayed?

We can assume that those bad mid-1990s teams would have been better, but it’s not only because of what Maddux himself would have brought to the team. As a whole, the starting pitchers had to carry a lot more of the burden with Maddux gone. After posting a collective 3.21 ERA in 1992, that number went up to 4.45 in 1993 and 4.53 in 1994. Mike Morgan and Frank Castillo saw their ERAs go up significantly from 1992 to 1993.

Maddux came back to the Cubs from 2004-2006, but he was past his prime at that point. Had Maddux had his prime Atlanta years in Chicago, he would have quickly become the greatest pitcher in team history, surpassing Fergie Jenkins. Instead, all we can do today is wonder, what if.