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On July 25, 2006, Cromartie signed a 5-year, $13.5 million contract with $7.35 million guaranteed with the Chargers.
In his first season with the Chargers, Cromartie saw action at cornerback and on special teams.
Toward the end of the season, Cromartie handled some punt and kickoff return duties.
Cromartie is credited with the longest play in NFL history, returning a missed Ryan Longwell field goal 109 yards for a touchdown on November 4, 2007.
He was a versatile player at Tallahassee's Lincoln High School. Cromartie also ran track in high school and placed 3rd in the 110-metres hurdles and as a member of the 4 x 100-metres relay team at the Class 5A County track meet. Cromartie decided to stay close to home for college and accepted an athletic scholarship offer from Florida State University, where he played for coach Bobby Bowden's Florida State Seminoles football team from 2003 to 2004.
Throughout his senior season, Cromartie recorded 12 tackles and 2 interceptions, returned 3 punts and 2 kicks for TDs, had 450 yards and 1 touchdown on 30 catches and ran the ball 13 times for 242 yards and 3 touchdowns. After flashing playmaking potential as a nickelback and kick returner his first two years, Cromartie tore the anterior cruciate ligament in his left knee in July, 2005 during voluntary workouts before his junior year and was forced to miss the entire 2005 season.This was enough to earn Cromartie 2002 USA Today defensive player of the year. He was potentially going to play at wide receiver during his junior year.In addition to football, Cromartie also joined the Florida State Seminoles track team in 2004.He was a member of the FSU track team that won the ACC Championship in 2004, where he placed 10th in the 200 meters with a time of 21.35 seconds.Despite being removed from competitive football for an entire year, Cromartie was still selected as the 19th overall pick of the first round of the 2006 NFL Draft by the Chargers based on his great potential.After not performing much at the NFL Scouting Combine, on March 16, 2006, just 8 months after surgery to repair his torn ACL, Cromartie performed at his pro day in 2006 for scouts.