Wentworth played high school football for the Whitney High School Wildcats. He earned Pioneer Valley League lineman of the year as the Wildcats finished with an 11-2 record, was named First-team All-PVC twice, first-team All-metro, first-team All-state, Whitney High School Athlete of the Year and played in the KCRA3 All-Star Classic. He also lettered in track & field as a thrower in the shot put (47-11 or 14.62m) and the discus (131-5 or 40.13m).[1]
Wentworth signed with the Minnesota Vikings on May 11, 2014, after going undrafted in the 2014 NFL draft. He was released by the Vikings on August 31 and re-signed to the team on September 2, 2014.[3] He made his NFL debut on October 26, 2014, against the Tampa Bay Buccaneers.[4] Wentworth was released by the Vikings on May 7, 2015.[5]
On May 13, 2015, it was reported that he was retiring due to blood clots in his leg. After surgery, he lost the muscle in his left leg that controlled the up function of his foot and will have to wear a brace for the rest of his life.[6]