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 eight 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. And he was going to have the future we all wanted for him. It's painful to us. We feel it in our hearts, and we will miss him."
Bengals receiver Andre Caldwell said: "People thought he was a bad guy, but he had a big heart."
Police released few details about the investigation, other than homicide detectives were assigned to the case. Two 911 tapes released Thursday and witnesses provided some clues.
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.
The first 911 tape was from an unidentified woman who said she was following a yellow pickup truck.
"It's got a black man on it with no shirt on, and he's got his arm in a cast and black pants on," she told a dispatcher. "He's beating on the back of this truck window. ... I don't know if he's trying to break in or something. It just looks crazy. It's a girl driving it."
Just over a minute later, an unidentified man called 911 and said he saw a man "laying in the road" and "definitely unconscious."
Police spokeswoman Rosalyn Harrington wouldn't say if the woman, whom police would not identify, was present at the scene when police arrived.
Henry and his 25-year-old fiancee Loleini Tonga, who grew up in Charlotte and received a volleyball scholarship to North Carolina A&T, were raising three children. Tonga's MySpace page identifies herself as "Mrs. C. Henry" and featured a post from Tuesday talking about buying wedding rings.
"We are greatly saddened by today's tragic news about the loss of Chris Henry," NFL commissioner Roger Goodell said. "Our thoughts and prayers go out to Chris' family, including his Bengals family."
Bengals coach Marvin Lewis said: "It's a very difficult thing with his loss and a young life and one that won't ever get to reach its full potential."
Police said the domestic dispute began Wednesday at a home about a half-mile away from where Henry was found. He had jumped into the bed of the pickup as his fiancee was driving away from the residence, and at some point when she was driving "came out of the back of the vehicle," authorities said.
Two women who lived nearby said Thursday they saw Tonga and the pickup at the scene when police arrived. Cheryl Hoffman said she came out with a blanket when she saw Henry wasn't wearing a shirt.
"When I got to where he was laying on the ground out there he was very unresponsive, laying flat on the ground," Hoffman said. "He was foaming at the mouth, and I was very worried what was happening then."
When players received word Henry had died, quarterback Carson Palmer called them together in the locker room and said they should dedicate the game and rest of the season to Henry and the wife of defensive coordinator Mike Zimmer, who died unexpectedly during the season.
The Bengals will wear a helmet sticker Sunday against San Diego to remember Henry, and Goodell requested clubs observe a moment of silence before each game.
"He was doing everything right," receiver Chad Ochocinco said. Henry grew up south of New Orleans in the suburban community of Belle Chasse and soon dreamed of playing in the NFL. But after he was ejected from a game and suspended for another at West Virginia, the Bengals were the only team to bring him in for a pre-draft visit in 2005.
Selected in the third round, Henry played a vital role as a speedy, deep threat as Cincinnati reached the playoffs in his rookie season. But in the final month of the season he was arrested for marijuana possession.
It was the first of five arrests, and Henry and former Tennessee cornerback Adam "Pacman" Jones became known as the league's two most trouble-bound players. Goodell suspended both in 2007 - Jones for a full season, Henry for half of it - as part of a toughening of the league's conduct policy.
After Henry was arrested for a fifth time following that season on an assault charge, Municipal Court Judge Bernie Bouchard called Henry "a one-man crime wave." He was released by the Bengals the same day.
But Brown gave him a second chance, re-signing him before the 2008 season.
"I kind of felt like I dug myself out of the hole and started doing the right things," Henry said in an interview with The Associated Press as training camp opened this season. "People say, 'How you feeling now Chris? You doing all right?' I just tell them I'm blessed. That's why I got it."
A thigh injury slowed him early in the season, and he had 12 catches for 236 yards - his 19.7-yard average per catch leads the team - when he broke his left arm during a win over Baltimore, ending his season.
"My grandma always says you never question the man upstairs on decisions he makes," Ochocinco said. "Everyone makes mistakes, but I don't see how Chris was supposed to go already, especially when he was on the right path. Other than that, he's going to be missed."
Associated Press Writer Mitch Weiss and AP Sports Writers Joe Kay in Cincinnati and Brett Martel and Mary Foster in New Orleans contributed to this report.