Shephard, who was actually released by Everton as a teenager, channelled his energy into a TV career instead.
One of West Ham's many famous fans
The TV celebrity first started going to matches in the famous 1985/6 season, when West Ham finished third but should have won the title.
Aged 12, Shephard was dragged along to a game by West Ham mad school mates and has never looked back.
The Hammers are getting ready to leave their beloved Boleyn Ground home of 112 years next summer when they move to the Olympic Stadium. They had to fight off bitter rivals Tottenham Hotspur for the keys to the 54,000 seater arena.
The East Londoners will be leaving so many memories behind, and one in particular sticks in Shephard's mind more than any other.
The game, and the atmosphere generated, has gone down in West Ham folklore.
'Tough to replicate Upton Park magic'
And Shephard told the club's official web TV channel it will be difficult to replace that special magic.
"I was hooked and vaguely remember being bowled over by the noise," Shephard told West Ham TV recalling his first game back in 1968.
"The noise and the energy and sound and feeling so grown because we were at the football and we were only 12. It was so exciting."
"My favourite game would be the play-off semi-final against Ipswich.
"It was the most extraordinary performance and the most magical, magical day and we won 2-0 which meant we got to the play-off final.
"I will never forget that feeling that day, you just felt invincible on top of the world because your team had done what they had to do and we'd cheered them every step of the way.
"I just didn't want that moment to end, I remember being stood there thinking I wonder if it's ever going to get any better than this and that still resonates to this day."
Shephard worrying unduly
Shephard's doubts are shared by some Hammers fans and it is only natural when the club is leaving such a massive part of their history behind.
But West Ham have already sold close to 40,000 season tickets for the Olympic Stadium with eight months still to go.
And it is the fans in the stadium which make it a special atmosphere, not the bricks, metal and mortar.