A native of New Jersey and graduate of Princeton University, Bradley coached in the American college game and Major League Soccer (MLS), managing the Chicago Fire, MetroStars, and Chivas USA over nine seasons.

Bradley was born and raised in New Jersey, playing soccer at West Essex High School and Princeton University.

[4] After two seasons with Ohio, Bradley worked as an assistant coach and scout for University of Virginia manager Bruce Arena for two years before taking the top job at his alma mater, Princeton.

After back-to-back championship seasons with DC, he became the first head coach of the Chicago Fire, an expansion team that began play in 1998.

Bradley began his tenure with the historically underachieving team headed in the right direction as the MetroStars advanced to the U.S. Open Cup final for the first time in club history in 2003 as well as earning a playoff berth.

In the knockout round, Bradley and the U.S. faced Ghana, who eliminated the Americans for the second consecutive World Cup with a 2–1 victory in extra time following a 1–1 draw.

On July 28, 2011, he was relieved of his duties by the United States Soccer Federation to be replaced by former Germany national team manager Jürgen Klinsmann.

[21] Egypt was perfect in its first six matches of qualifying for the 2014 FIFA World Cup, but fell decisively to Ghana in the third round playoffs.

[24] On November 10, 2015, Bradley was officially named as the new manager of French Ligue 2 side Le Havre AC, signing a two-year contract.

Bradley managed his final match on October 3, 2016, a league home game against Sochaux, which Le Havre won 2–1.

[31][32][33][34][35][36] On December 27, 2016, following a 1–4 defeat by West Ham United, Bradley was sacked by Swansea after only 85 days and 11 games in charge of the club,[37] the fourth shortest reign of any manager in the history of the Premier League.

Unfortunately things haven't worked out as planned and we felt we had to make the change with half the Premier League season remaining.

On November 18, 2021, 11 days after LAFC failed to qualify for the playoffs for the first time, Bradley and Los Angeles FC parted ways.

[46] On November 24, 2021, Bradley was announced as head coach and sporting director of Toronto FC, reuniting with his son Michael, who has been the club's captain since 2015.

[47] He tied 1–1 at FC Dallas on his debut the following February 26,[48] concluding his first season in second-from-bottom in the Eastern Conference; the team signed Italian international trio Domenico Criscito, Lorenzo Insigne and Federico Bernardeschi in July 2022.

[53] He was unable to prevent the team from relegation to the Norwegian First Division, but his contract was renewed, with his son Michael joining him as a volunteer coach.

Their son, Michael, was drafted by the MetroStars in the 2004 MLS SuperDraft, and played in the Eredivisie, Bundesliga, Premier League and Serie A before transferring to Toronto FC in January 2014.

[58] Bob also has a daughter named Ryan, who is married to Andy Rose, a former professional soccer player for Vancouver Whitecaps FC and current assistant coach for Seattle Sounders.