But now, credited with being a mentor and a wise voice of experience in the San Francisco 49ers locker room, the 35-year-old wide receiver is making an unexpected trip back to the Super Bowl in the twilight of his career.
Moss had a touchdown for the New England in his only Super Bowl, at the end of the 2007 season, collecting on a six-yard pass from Tom Brady to put the Patriots ahead before Eli Manning led the New York Giants on a game-winning drive.
It is surprising that the Brady-Moss combination, which produced a single-season record 23 touchdown receptions for the receiver in that year, did not deliver a Super Bowl ring.
Certainly Moss's four seasons in New England did enough to put him in line for a place in the Pro Football of Fame.
"He's probably the smartest receiver I've ever coached," said Patriots coach Bill Belichick.
But now Moss has an unexpected second chance to finally slip on a Super Bowl ring, championship a little over a year after he turned his back on the game of American football.
After being surprisingly cut by the Patriots early in the 2010 season, Moss's once-stellar career faded quickly.
He had a short and unhappy spell with the Minnesota Vikings, where he started his career in 1998 and first made his name for himself, before being cut and then an equally brief time with the Tennessee Titans.
In August 2011, Moss decided to retire and he sat out an entire season before deciding, in the following March, to work out for 49ers head coach Jim Harbaugh.
Harbaugh had clearly decided that he needed some veteran input into his receiving corps but many were surprised that Moss was his choice.
"The thing about me being here is that they've done their research on me. When it comes to the worldwide sports media, I've gotten a bad rap," said Moss, who signed a one-year deal with the 49ers last March.
"But they have done their homework on me or they wouldn't have brought me in here."
Any doubts about the wisdom of Harbaugh's decision have been erased not particularly by Moss's play on the field - he had just 28 receptions for 434 yards and three touchdowns during the regular season - but by his role in the locker room.
Young receiver Michael Crabtree, who has put up a career-best 1,105 receiving yards on 85 catches this season, has particularly benefited from Moss's influence.
"Randy talks to us all the time," Crabtree said recently, "I'm in the room with Randy all day, every day. There's a lot of things we're talking about."
Moss has also impressed his team mates with his ability to help out with blocking duties.
"I was really surprised. Randy's tried his best to do everything - catching and blocking and he's been doing a great job," said running back Frank Gore.
On Sunday, in the 49ers thrilling comeback win over the Atlanta Falcons in the NFC Championship game, Moss had three receptions for 46 yards, an unspectacular performance, typical of his new role, but one which came a day after Harbaugh had said he wanted the veteran back for another year.
"I for one definitely want Randy to come back," said Harbaugh, "I hope he feels the same way".
Before he turns his thoughts to that prospect, Moss has a trip to New Orleans for the Feb. 3 Super Bowl and the chance to claim a prize that has eluded him.
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