Prior to joining the Bears, Angelo spent 14 years overseeing Tampa Bay Buccaneers' scouting department as their director of player personnel.

An expansion team established in 1976, the Buccaneers lost the 1979 NFC Championship Game to the Los Angeles Rams.

The Bears went from 5–11 in 2004, to 11–6 in 2005 (including a playoff loss to the Carolina Panthers) to a team in 2006 that went 15–4 after losing Super Bowl XLI to the Indianapolis Colts.

Further damping the Bears off-season was a prolonged contract battle with star linebacker Lance Briggs, who eventually had the franchise tag placed on him.

"[3] Rather than pursuing the league's top free agents, Angelo focused the team's resources on securing players that were already members of the team, including Lance Briggs, Alex Brown, Tommie Harris, Kyle Orton, Rex Grossman, and Devin Hester.

On July 24, 2008, the second day of the Bears Training Camp, Williams was forced to leave practice due to back spasms.

The 2008 Chicago Bears finished with a 9–7 record, and missed the playoffs after losing their season finale to the Houston Texans.

[13] He also commented on the team's need to acquire a stable quarterback, dismissing rumors that Kyle Orton was the franchise's long-term solution.

We’re fixated on that.”[15] In March 2009, Angelo, along with several other NFL teams, expressed interest in acquiring Pro Bowl quarterback Jay Cutler from the Denver Broncos.

Cutler, who had spent three years with Denver, requested to be traded after head coach Josh McDaniels considered replacing him with Matt Cassel.

Ted Phillips, the Bears president, confirmed that neither Angelo nor Lovie Smith would be dismissed for the team's disappointing finish.

The reason for his firing was due to a combination of poor drafting and questionable free agent signings, with the team stating they wanted to "close a talent gap" to stay competitive with the rival Green Bay Packers and Detroit Lions in the NFC North.