He also decisioned future world champions Don Wilson, Ted Pryor, Dale "Apollo" Cook and Bob "Thunder" Thurman.

Promoting principally out of West Palm Beach Auditorium, he was the first kickboxer to draw over $1 million in live gate receipts.

After retiring from the ring, he trained, managed and promoted over 200 state, golden gloves national and world champions; both amateur and professional.

He also ran Shepherd's Boxing & Kickboxing Center for over 25 years which became a favorite South Florida training facility for a multitude of popular champions: Don "The Dragon" Wilson, Bill “Superfoot” Wallace, Oscar De La Hoya, Zab Judah, Michael Moorer, Kassim Ouma and others.

[5][6] Early on, Shepherd scored wins over Florida cult legends Gator Garland, Bill Clarke, Harold "Nature Boy" Roth (a.k.a.

[2][7] In November 1981, Shepherd challenged PKA heavyweight world champion Demetrius "Oaktree" Edwards in an effort to embarrass the sanctioning body for having stripped his title.

However, in 1982 an improperly dieted and badly dehydrated Shepherd lost his title in Las Vegas over nationally syndicated TV to that same John Moncayo.

[12] One year later, in 1983, Shepherd moved up in weight to capture the WKA super middleweight world title from Japan's Yasuo Tabata in a close split decision.

[2] Shortly afterward, he was diagnosed with a ruptured disk in his neck that most probably occurred during his extraordinary battle against heavyweight champion Demetrius Edwards.