He attended Ann Arbor Pioneer High School where he was a star football player as a running back and a track and field athlete.
[1] In football, Bailey led Pioneer to a Michigan Class A state title as a junior with 1,100 rushing yards on the season.
[3] In 1989, Bailey was named to the Detroit Free Press 1980s Michigan football Class A All-Decade team.
[5] Bailey enrolled at Eastern Michigan for the 1989–1990 academic year, but was forced to sit out of football for one season due to the NCAA's Proposition 48 eligibility rule requiring that student-athletes maintain a specific grade point average or standardized test score while in high school.
[6] As a sophomore at DuPage, Bailey began the season as a safety and kick returner before he was moved to running back.
DuPage went 11–1 on the season after defeating Fort Scott Community College (KS) in the Midwest Bowl.
[10] Following his successful stint at DuPage, Bailey received a scholarship offer from the University of Louisville.
[18] Bailey went undrafted in the 1994 NFL draft, but was signed by the Indianapolis Colts as a rookie free agent on May 7, 1994.
[19] In his first season with the Colts, Bailey saw limited action behind wide receivers Sean Dawkins and Floyd Turner.
Bailey caught a 21-yard pass from quarterback Jim Harbaugh to tie the game in the fourth quarter before Cary Blanchard kicked the winning field goal in overtime.
[22] The Colts finished the regular season at 9–7 and earned a Wild Card spot in the 1995-96 NFL playoffs.
Trailing 20–16 with time for one last play, quarterback Jim Harbaugh threw a Hail Mary pass that was tipped by Pittsburgh strong safety Myron Bell.
As Bailey was falling to the ground, the ball ended up in his arms but was knocked free by Pittsburgh cornerback Randy Fuller.
[23][24] Bailey took over as the starting kick returner in the 1996 season, while he continued to back up Dawkins and rookie Marvin Harrison at wide receiver.
[20] Bailey's lone touchdown on the season came in the final week against the Cincinnati Bengals when he returned a fourth-quarter kickoff for 95 yards.
Following the 1998 season, Bailey was one of five players left unprotected by the Colts in the 1999 NFL expansion draft for the reactivated Cleveland Browns.
He played in the XFL's lone season, where he was part of an Enforcers team that went 5–5 before losing in the playoffs to the Los Angeles Xtreme.
[31] Bailey was signed by the Carolina Cobras of the Arena Football League (AFL) on May 30, 2001, as an offensive specialist.
[32] He joined the Cobras mid-way through their 2001 season, but still led the team in receiving with 61 receptions for 951 yards and 19 touchdowns.
They beat the Grand Rapids Rampage in the first round before losing to the Arizona Rattlers in the quarterfinals.
They beat the Georgia Force in the Quarterfinals of the 2003 AFL playoffs before losing to the Arizona Rattlers in the Semifinals.