Holes in the Tar Paper

Holes in the Tar Paper: A memoir of hits, misses, and ceilings that leak raindrops and hope

Dan “Shamrock” Calloway was a self-taught 14-year-old baseball phenom, playing in the Negro League among respected icons of the game. “One of the worst and best days of my life,” Dan writes, “was suffering a humiliating loss to an aging Satchel Paige who was pitching for a barnstorming team. After the game, Jackie Robinson came over, put his arm on my shoulder, and said, ‘Good game little man. You going to be just fine.’”

That one loss lit a fire under Calloway, and his raw talent soon caught the attention of Major League scouts. After high school graduation, he signed with the Pittsburg Pirates. An article in the Pittsburg Courier referred to Calloway as the next Willie Mays. Sadly, during spring training, Dan suffered a career-ending injury which prompted his return home to Riviera Beach Florida.

Undaunted, he continued his love for the game. In 1963, as Captain of Special Services, "Shamrock" became the first Black manager of the Army baseball team. For his winning accomplishments, he made All-USAREUR and became a German Sports Hall of Fame inductee. Returning stateside, he became caddy master at the renowned Seminole Golf Club and carried bags for entertainers, public figures, and legends Ben Hogan, Arnold Palmer, and Jack Nicklaus. He also caddied in a foursome that included the late President John F. Kennedy.

Mr. Calloway has helped mold the lives of thousands of young people throughout the country, many of whom enjoyed professional sports careers. His mentorships include NFL standouts Lamar Parrish and Otis Anderson to LPGA championship golfer and fashionista Michelle McGann and many in between. The Dan Calloway Recreational Complex, a multi-million-dollar sports and event facility, is further testament to the enormous impact he has had in the community.

In Holes in the Tar Paper, Dan Calloway’s poignant storytelling weaves together colorful tales of a rebellious early life in segregated Palm Beach County with his distinguished careers in sports, law enforcement, and community advocacy. His stories serve as thoughtful meditations on race, family, courage, and aging. In this candid, revealing memoir, readers get an intimate look into the disciplined mind of a Palm Beach County legend turned hero. He shows readers that despite humble beginnings, you can do whatever you dare to dream.