Indeed, his multiple arrests during a five-year NFL career were among the factors prompting the league to toughen its personal conduct policy.
But to hear his teammates tell it -- even the team's owner -- the Cincinnati Bengals receiver was determined to leave behind his troubled past and move ahead toward a bright future.
Tragically, his efforts were cut short when he died from injuries in what police said was a domestic dispute with his fiancee.
Charlotte-Mecklenburg police said the 26-year-old Henry died early Thursday, less than 18 hours after he fell off of the back of a pickup truck on a curvy residential street about 8 miles northwest of downtown Charlotte.
The cause of death was not immediately released.
Henry was away from the Bengals after suffering a season-ending broken forearm in a game last month.
"We knew him in a different way than his public persona," Bengals owner Mike Brown said. "He had worked through the troubles in his life and had finally seemingly reached the point where everything was going to blossom."
Bengals receiver Andre Caldwell said: "People thought he was a bad guy, but he had a big heart."
Police provided few details about the investigation, other than that homicide detectives were assigned to the case.
Henry and his 25-year-old fiancee, Loleini Tonga, who grew up in Charlotte, were raising three children.
Neighbor Lee Hardy told WLWT-TV and The Cincinnati Enquirer that he was working in his yard when the truck left the driveway. Hardy said Henry was yelling that he needed to talk to the woman behind the wheel.
"He said, 'If you take off, I'm going to jump off the truck and kill myself,' " Hardy told the newspaper.