What if Greg Maddux had never left the Cubs to join the Braves?

The Chicago Cubs have retired the number 31 for two players. Fergie Jenkins spent ten of his nineteen years in the league on the North Side and went into the Hall of Fame as a Cub. The other is Greg Maddux, who spent ten of his twenty-three years in the league with the Cubs. He went into the Hall of Fame with a blank cap.

While it took a couple years for Maddux to get going in the league, he became one of the greatest to ever do it. His first six full years in the league progressed more and more, the team just failed to come together around him. In the winter of 1992, he decided to sign as a free agent with the dominant Atlanta Braves, kicking off what was poised to be one of the most dominant stretches in baseball history.

Thanks in part to Maddux, the Braves won their division every year with him and made it to the World Series three times, winning it all in 1995. Maddux ended his career with four Cy Young awards, eight All-Star appearances and a staggering eighteen Gold Gloves. All this (at least to a Cubs fan) begs the question: what if he’d stayed in Chicago?

What if Greg Maddux signed his second contract with the Chicago Cubs?

Needless to say, had Maddux stayed with the Cubs in the nineties, the Cubs would have been a better team. Based on Maddux’s WAR (wins above replacement) from 1993-1999, here is how much better the Cubs (hypothetically) could have been.

• 1993: Without Maddux (84-78-1, 4th in NL East), With Maddux (90-72-1, 3rd in NL East)
• 1994: Strike year, N/A
• 1995: Without Maddux (73-71, 3rd in NL Central), With Maddux (83-61, 2nd in NL Central & Wild Card Birth)
• 1996: Without Maddux (76-86, 4th in NL Central), With Maddux (83-79, 2nd in NL Central)
• 1997: Without Maddux (68-94, 5th in NL Central), With Maddux (76-86, 3rd in NL Central)
• 1998: Without Maddux (90-73, 2nd in NL Central & Wild Card Birth), With Maddux (97-66, 2nd in NL Central & Wild Card Birth)
• 1999: Without Maddux (67-95, 6th in NL Central), With Maddux (64-92, 6th in NL Central)

The Results

In conclusion, there are realistically only two years (again, hypothetically) things look to make an impact if Maddux were to stay – in 1995 and 1998. In ’95, the Cubs would have received a Wild Card spot to take on Maddux’s Braves in the Divisional Round. Likewise in ’98, the Cubs did actually and still would have faced the Braves in the same spot.

Who knows? Maybe things swing in favor of the Cubs in both of those instances. Maybe from there, Maddux wills the team into an improbable run for the World Series. We’ll never know, but it’s nice to think we could have ended our drought twenty years earlier.