Bailey attended Miami Southridge High School, where he lettered in football and track & field.
The tip of Bailey's left ring finger was torn off while playing against the Detroit Lions and he was placed on injured reserve for the remaining games.
On October 23, 1994, Bailey made the longest punt return in NFL history when he ran 103 yards for a touchdown in a game against the New Orleans Saints.
[4] What makes this return stand out is that every single player on the field assumed the ball was going to bounce through the end zone after the punt.
On September 12, 1995, he signed as a free agent with the Washington Redskins to take the place of the injured Muhammad Oliver.
[7] He played mainly as a special teams player, until being named the nickel back after Clayton Holmes was suspended under the NFL substance abuse policy.
The next year, he started 11 games at left cornerback and had 65 tackles, 2 interceptions, 24 passes defensed, 2 sacks and 2 forced fumbles.