Theo Epstein’s run with the Cubs is over, his legacy in Chicago secured.
Epstein resigned from his position as Cubs president this week, ending a nine-year tenure that brought the Cubs their first championship since 1908. When he joined the organization nine years ago, he set out to build a culture of sustained success — and accomplished just that, with the Cubs making five postseason trips in the past six seasons.
Epstein was the architect of the Cubs’ rebuild, drafting core hitters in Kris Bryant, Kyle Schwarber and Ian Happ, acquiring a face of the franchise in Anthony Rizzo and a future Cy Young Award winner in Jake Arrieta, and securing the best free agent signing in team history in Jon Lester — not to mention Ben Zobrist, Jason Heyward and more.
What about the moves that didn’t work out? You can argue expectations for this Cubs group were greater, but in looking back at Epstein’s tenure, it was difficult to come up with a list of sure-fire misses he made in trades and free agency.
This goes to show how successful he and his front office have been. That said, here are the five worst moves, which sounds harsh considering they're among a list with far many more good ones. Some notable exclusions:
-José Quintana: He wasn’t the same pitcher as he was with the White Sox but wasn’t bad in three-and-a-half seasons, all while being durable on a team-friendly contract. The Cubs gave up top prospects to get him, but whether they won the trade or not is a different discussion.
-Daniel Descalso: His offensive performance is well-documented, and the Cubs replaced a 2019 All-Star in Tommy La Stella with him. The deal didn’t work out, but it only cost $5 million.