But he will kick off a career path that very few of his fellow footballers have ever gone down before this weekend when he will be back on the front cover - this time to highlight his work as an accomplished artist.
Former defender Craddock, now 42, was already gaining notoriety for his artwork long before his retirement from football in May 2013.
And, although he admits his past footballing connections do still open some doors, his continuing success in this new environment has rarely involved actually painting anything to do with this country's national game.
But he has been persuaded by John Hendley and Paul Berry in the club's media department to do the front cover artwork for all of Wolves' home match programmes this season, starting with Saturday's Championship opening day fixture against Middlesbrough.
"They first approached me a few years ago," Craddock, who still lives in the same house in the village of Cookley, near Kidderminster, Worcestershire, which he and wife Shelley chose when he first arrived from Sunderland in 2003, told BBC Sport.
"I just didn't have the time or the ideas then. I was still playing, which made it more difficult, so I declined.
"But when they came back to me again I couldn't turn it down a second time," added Craddock, who is still a regular at matches at Molineux with the couple's three boys Joseph, Luke and Toby.
"I've had to give it a lot of thought as to what might appeal to the fans. The idea I had was kind of comic-book heroes. But also taking into account that, at Wolves, we already have our heroes on the pitch, the Billy Wrights and all the other legends of the club.
"My regular stuff can take two to three weeks to do. I couldn't do that with these as, with 23 programme covers, that would take me over a year and a half. But I've been working hard for the past four months to get them all ready in time."
Having met his own personal deadline to get all the covers done in time for the start of the new English Football League season this weekend, Craddock was forced into a rethink when he heard of the plight of his former Wolves team-mate Carl Ikeme, 31, who was diagnosed with leukaemia at the start of July.
It is a disease that has touched the Craddock family too. His youngest son Toby was also diagnosed with leukaemia in 2012 at the age of two and a half.
Craddock's original choice for the front cover for Saturday's game with Middlesbrough was former West Ham United, Manchester United, Inter Milan, Liverpool and England captain Paul Ince, who put in sterling service late in his career with both Boro and Wolves.
But Craddock also wanted to show his support to Ikeme. And the solution was simple. He just went back to his easel and knocked out another picture, in tribute to the goalkeeper.
The club will now not only use that as the front cover on Saturday but also the legendary Ince on page three - to give the fans a taster of what is to come.
Most of Craddock's professional artwork these days is non-football related.
He held his first exhibition, "Le Bellezza Della Fusione", demonstrating his own, unique style of portraiture, graffiti and photorealism, over in Leicestershire in 2015. And he is booked in to do the same at a gallery in Chester this autumn.
But the sight of a football net in his back garden in Cookley absolutely festooned with kids' footballs is a reminder that he is a football man and also a football fan at heart.
And his portraits of past and present players, whether Pele or John Terry, or simply his regular commissions for ex-Wolves players, are a reminder that he too is excited at the start of another new season - especially at Molineux, where Wolves' Chinese owners Fosun have spent big on new signings, including new club record purchase Ruben Neves.
But are Wolves in the frame to repeat the promotion Craddock and his team-mates enjoyed from the Championship under Mick McCarthy in 2009?
"Another new manager has come in," he said. "There's a lot of new players and everybody wants to impress.
"It's so physically demanding in this league, playing Saturday/Tuesday all the time. But, if we can keep the injuries down, then we're all excited about what's to come this season."
Jody Craddock was accustomed to seeing his face on the front cover of the match programme at Molineux during his 10 largely successful years as a Wolves player.