New York playground legend, HBCU star passes

Harold "Funny" Kitt, the former Winston-Salem State star and New York playground legend who brought Stephen A. Smith to the HBCU has passed away.

Funny Kitt's impact on Winston-Salem State basketball stretched far beyond his own playing days. He was the man who helped connect Smith to WSSU, a relationship that later became part of Smith's well-known origin story in sports media.

Smith later told Ebony that Kitt took him to Winston-Salem for a tryout with the legendary WSSU coach.

"I was introduced to Clarence ‘Big House' Gaines by a former player of his - by the name of Harold ‘Funny' Kitt," Smith said. "He took me down to Winston-Salem for a tryout with Winston-Salem State and Clarence ‘Big House' Gaines. He put me on the court with them and he said, you're on your own now."

Funny Kitt made his name on New York playgrounds before WSSU

Before he became a star at the HBCU, Funny Kitt was already a playground legend in New York.

The 6-foot-2 guard came out of the Bronx basketball world. His name carried weight on the asphalt before he ever reached Winston-Salem. He was mentioned in Pete Axthelm's 1970 classic The City Game, a book that documented the mythology of New York playground basketball.

Kitt's game was built for that world. He had flair, confidence and no fear. He played against and around some of the biggest names in the sport. His playground résumé included games involving Lew Alcindor, Wilt Chamberlain, Charlie Scott, Dean Meminger, Tiny Archibald and Pee Wee Kirkland.

The nickname "Funny" came from his unusual shot. People saw the motion and called it a funny shot. The name stuck. So did the reputation.

Kitt was not a quiet player. He was a scorer. He was a competitor. He wanted the ball. He wanted the moment.

From New York asphalt to Big House Gaines

Funny Kitt arrived at Winston-Salem State after transferring from Sheridan Junior College in Wyoming. He sat out the 1970-71 season because of transfer rules. Once eligible, he became one of the signature players of WSSU's post-Earl Monroe era under Big House Gaines.

Kitt finished his Rams career with 1,271 points in 78 games. He averaged 16.3 points per game. He led WSSU in scoring during the 1971-72 season and again in 1973-74. His senior season was his best, as he averaged more than 22 points per game and earned All-CIAA honors.

He also helped bring "Showtime" back to Winston-Salem basketball.

In January 1972, Kitt scored 27 points, grabbed 10 rebounds and added six assists in an 89-56 win over North Carolina Central. He shot 10-for-15 from the field that night. The performance gave WSSU fans a flash of the style and excitement they had come to expect under Gaines.

A fearless scorer and a one-of-one personality

Funny Kitt was not just remembered for numbers. He was remembered for presence.

Those who saw him play described a fearless scorer. He could score 30 points. He could also miss 30 shots. He would throw up 35-foot shots a decade before there was a 3-point line. Either way, he was not afraid of the next attempt.

That made him both thrilling and unpredictable. It also made him unforgettable.

Kitt's game reflected his background. He wanted pace and he liked space. He believed college basketball needed a shot clock long before that became standard. Kitt wanted the game to move. He wanted players to compete.

He was also known for loyalty. Friends remembered a hard exterior that often protected a softer side. If Funny Kitt liked you, he was all in.

A lasting HBCU basketball legacy

Kitt was inducted into the C.E. "Big House" Gaines Hall of Fame in 2007. It was a fitting honor for a player whose story stretched from the Bronx playgrounds to one of the greatest HBCU basketball programs ever built.

He later earned his bachelor's degree in Health and Physical Education from WSSU in 1975. He also earned a master's degree in education from City College of New York in 1985. His life after basketball included coaching, teaching and youth work in New York and North Carolina.

Funny Kitt's legacy is bigger than one box score. He was a bridge between worlds. New York playgrounds. CIAA basketball. Big House Gaines. Stephen A. Smith. Winston-Salem State.

He was an HBCU star with a playground legend's soul.

And his story will live wherever people still talk about players who made the game feel larger than life.

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This story was originally published May 18, 2026 at 9:25 PM.