We Finally Know What Former Bears President Ted Phillips Thinks Is His Biggest Mistake

Ted Phillips was team president for the Chicago Bears for over 20 years. In that time, he did some good things. He helped renovate Soldier Field in the early 2000s, overhauled Halas Hall to make it the envy of the NFL, and put the team on a path to their first new stadium in franchise history. Unfortunately, his legacy is marred by a significant dip in overall team success compared to previous eras. Between 1999 and 2022, the Bears made the playoffs five times. Their biggest highlight was losing the Super Bowl in 2006 and the NFC championship in 2010.

It isn't what Phillips wanted, and he acknowledges that. The former president has said his biggest regret was never getting the quarterback position. There were certainly missed opportunities. Aaron Rodgers slipped by in 2006, and of course, Patrick Mahomes in 2017. However, people have always wondered what he thinks his biggest mistake is. A decision that ended up sending the team in the wrong direction. Jeff Hughes of Da Bears Blog finally revealed what it is. It might not be your first guess, but it should be.

Ted Phillips will never live down the Phil Emery experiment.

The 2011 season was a disappointing one for the Bears. After starting 7-3, an injury to Jay Cutler saw the team finish 8-8. This led Ted Phillips to fire GM Jerry Angelo, which was a surprise to many. Still, maybe a fresh voice might do the team good. There were some promising options available, like Les Snead and Tom Telesco. They interviewed Jason Licht, who eventually got the Buccaneers job in 2014 and built them into Super Bowl champions. Ultimately, Phillips went with Emery, a former Bears scout he knew personally from 1998 to 2004.

Everybody knows what followed. The GM's first-ever draft pick was Shea McClellin, a major bust. After a 10-6 season, Emery fired head coach Lovie Smith, replacing him with the even older Marc Trestman despite interviewing Coach of the Year Bruce Arians. Brian Urlacher was pushed into retirement, and the team bottomed out at 5-11 by the end of 2014. The locker room was horribly fractured, and the championship window slammed shut. Truth be told, the organization still hasn't fully recovered from that fiasco.