Henry was a Parade All-American[1] and "Mr. Florida Football" as a running back at Frostproof Middle-Senior High School.
[5] Henry did not play much in his freshman season due to a very crowded and talented backfield, which contained future NFL running backs Jamal Lewis and Shawn Bryson.
[8] In the 1999 season, Henry continued to share the backfield with fellow running back Jamal Lewis and collected 125 carries for 790 yards and eight touchdowns.
[9] In Henry's senior season, in which he rushed 253 times for 1,314 yards and 11 touchdowns,[10] he was named first-team All-SEC by the Associated Press and the Sporting News.
[25] In Week 4, against the Chicago Bears, he scored his first receiving touchdown in the NFL on a 26-yard reception from Drew Bledsoe to win the 33–27 game in overtime.
[42] In the 2004 season, Henry was injured for the later part of the year and lost his starting job to the Bills' 2003 first round pick, Willis McGahee, in Week 8.
Henry was suspended four games during the 2005 season for violating the NFL's substance abuse policy.
[53] On Christmas Eve in 2006, Henry broke the 1,000 yard mark for the 2006 NFL season against his former team, the Buffalo Bills.
In the regular season opener against the Buffalo Bills, he had 183 scrimmage yards (139 rushing, 44 receiving) in the 15–14 victory.
[60] According to an article written by MyFOX Colorado, it was reported that Henry faced the possibility of being suspended for the remainder of the 2007 season for a positive marijuana test.
Henry appealed the suspension and his case was taken to Federal courts, allowing him to play until a decision was made.
[65] On February 21, 2008, Henry restructured his contract with the Broncos prior to his scheduled $6 million bonus to stay with the team.
"[67] On June 2, 2008, Henry was released from the Denver Broncos just one year into his five-year, $22.5 million deal.
"We did not feel his commitment to the Broncos was enough to warrant a spot on this football team," said head coach Mike Shanahan in a prepared statement.
[70] On August 31, 2008, Henry was suspended for at least one year by the NFL for violating the league's substance abuse policy.
[74] Henry has had on-going problems making his child support payments to the mothers of nine of his children.
He was arrested in Polk County, Florida, in March 2009 and charged with failing to pay $16,600 in child support.
[73] On September 30, 2008, Henry was arrested by the DEA after allegedly being involved in a multi-kilogram cocaine transaction that occurred in Centennial, Colorado.
[77] On March 31, 2009, Henry and prosecutors reached a plea agreement; a change-of-plea hearing was set for April 16 by the judge.
[78] The plea deal consisted of Henry accepting a charge of conspiracy to possess cocaine with intent to distribute.
The maximum penalties included serving ten years to life in prison, and a fines of up to $4 million.
[79] On July 15, 2009, Henry was sentenced to three years in federal prison for financing a cocaine trafficking operation.
In addition, if Henry completed a drug program while in prison, his sentence could be reduced by one year.