In 2000 Bentley and Northwestern won a share for the Big Ten champion with Michigan and Purdue. Bentley helped lead Northwestern to their first bowl game since the 1997 Florida Citrus Bowl. They went on to face off against Nebraska in the 2000 Alamo Bowl, though they ended up losing by a score of 66–17.
Bentley was selected by the Cleveland Browns in the fourth round, with the 101st overall pick, of the 2002 NFL draft.[3] He officially signed with the team on July 16, 2002. He became a free agent after the 2004 season.[4]
Seattle Seahawks
Bentley signed a contract with Seattle Seahawks in the 2005 season. He helped lead the Seahawks to the NFC Championship Game and beat the Carolina Panthers by a score of 34–14. They would face the Pittsburgh Steelers in Super Bowl XL, though they would fall short by a score of 21–10. He became a free agent after the 2007 season.[4]
Houston Texans
Bentley signed a free agent contract with the Houston Texans on March 2, 2008.[5] He became a free agent on July 26, 2011.[4]
San Diego Chargers
On August 24, 2011, Bentley signed with the San Diego Chargers. He was released during final cuts.[6]
Jacksonville Jaguars
The Jacksonville Jaguars signed Bentley on November 22, 2011. He was released on December 5.[6]
Bentley earned his MBA from Rice University in 2015, and is currently a Cert-III level snowboard coach with Team Summit Colorado.[7] He is currently on the MGA TOUR with the ATLMGA chapter. His alias is "Smart Stick" or #KBCLOSE