He played college football for the Georgia Bulldogs, where he earned consensus All-American honors, and was selected by the Washington Redskins in the first round of the 1999 NFL draft.

[1] Bailey was born in Fort Campbell, Kentucky[2] and grew up in Folkston, Georgia, where he was a three-sport athlete (football, basketball, track) at Charlton County High School.

He was regarded as one of college football's greatest multiple threats (offense, defense, and special teams) in his three seasons as a Bulldog.

In his final year at Georgia, he registered 52 tackles (four for losses), three interceptions, seven passes deflected, 47 catches for 744 yards (15.8 avg.

[14] He was a large presence on the Redskins defense and benefited from time spent with eventual Hall of Fame cornerback teammates Deion Sanders and Darrell Green.

After the 2003 season, Bailey's contract with the Redskins expired and he threatened to boycott training camp if the club exercised the franchise tag.

On September 12, 2004, during the NFL's opening Sunday Night Football game of the season against the Kansas City Chiefs, Bailey intercepted his first pass as a Denver Bronco.

On January 14, 2006, in a Divisional Round playoff game against the defending champion New England Patriots, he broke the record for the longest non-scoring play in NFL history at the time.

In 2006, Bailey had 10 interceptions (tied for best in the NFL with Patriots cornerback Asante Samuel) and did not give up a touchdown during the season.

Bailey, San Diego Chargers running back LaDainian Tomlinson and Miami Dolphins defensive end Jason Taylor were unanimous choices for the NFL All-Pro team.

In 2009, Bailey did not allow a touchdown in 80 passes thrown his way that year, played on 98% of the snaps and remained one of the best-tackling cornerbacks in the game.

[19] It was announced on February 22, 2011, by the Broncos vice president of football operations, John Elway, that Bailey was re-signed to a 4-year contract.

[22] On December 6, 2012, Bailey recorded the 52nd and final interception of his career, picking off Carson Palmer in a 26–13 victory on Thursday Night Football over the Oakland Raiders.

[23] During the 2012 AFC Divisional Round against the Baltimore Ravens, Bailey was beaten woefully multiple times on deep routes by Ravens wide receiver Torrey Smith, who totaled 98 yards for two touchdowns on three catches as Baltimore would go on to win in dramatic fashion 38–35 in double overtime, en route to eventually winning Super Bowl XLVII.