Henderson attended Cretin-Derham Hall High School and originally signed a letter of intent to play college football at the University of Southern California,[3] but was granted release from his commitment by Coach Lane Kiffin in July 2010 and eventually committed to the University of Miami.

[6] Henderson made the All-USA team in 2009 again, and was also named Offensive Player of the Year, the first lineman to do so in the 28-year history of the award.

[10] In 2009, Henderson helped Cretin-Derham Hall to a 5A state championship and was named Minnesota Player of the Year by the Associated Press.

[1] He played for the "Howard Pulley Panthers" on the AAU circuit alongside Harrison Barnes, one of the nation's top basketball prospects.

At that point, Notre Dame, USC, Ohio State and Michigan were mentioned as leading contenders.

Henderson's former Cretin-Derham Hall teammate Michael Floyd was playing for the Notre Dame Fighting Irish.

Henderson scheduled his fifth and final official recruiting visit to the University of Miami for the 2010 Pro Bowl weekend in late January.

[15] He verbally committed to the Trojans, but did not sign his letter of intent until after USC went before the NCAA infractions committee on February 19 to respond to allegations relating to a scandal involving Heisman Trophy-winning tailback Reggie Bush.

[4] As a true freshman at Miami, Henderson played 12 games (including 9 starts) and saw most of his action at right tackle.

[32] In 2016, Henderson underwent surgery and another operation to remove all infected areas and reattach his intestines before announcing that he would return to the team.

[33] Henderson was suspended for the first four games of the 2016 NFL season for violating the league's substance abuse policy.

[35][36] Henderson admitted that he used marijuana to deal with the pain from his Crohn's disease and the two intestinal surgeries from earlier in the year.