At 6’4” and 250 pounds, Willie “Chip” Holmes was known throughout Chicago’s softball community as a gentle giant, admired not just for his imposing presence but for his extraordinary talent and humble spirit. His love for softball took root in the late 1960s in the Robert Taylor Homes projects, one of the city’s most storied neighborhoods. By the age of 15, Chip was already leaving his mark on the game. His powerful swing often sent softballs crashing into the towering 16-story buildings, breaking windows and reaching as high as the sixth floor — feats that quickly earned him a reputation as a rising star. Chip began his career playing for the Demons, a team based out of Rosenblum Park at 75th and Jeffery. His natural talent and explosive power at the plate made him a standout player. In 1967, the Ironmen of the Daddy-O-Daylie league recognized his potential and brought him onto their team. That same year, at just 17 years old, Chip earned the league’s Rookie of the Year award, solidifying his place as one of Chicago’s brightest young athletes. During his decade with the Demons, Chip became one of the league’s most dangerous hitters. He racked up an impressive 8 Home Run Champion titles and 3 MVP awards, helping to lead his team to numerous victories. Despite his loyalty to the Demons, Chip was also sought after by other teams for tournament play, a testament to his remarkable skill and leadership on the field. He contributed to teams like the Flamingos and the Senators, consistently delivering clutch performances. While with the Senators, he added three more MVP awards to his growing list of accolades. One of the highlights of Chip’s career came in 1979 when he helped the Flamingos win the World Series of Softball Tournament at Lou Boudreau Stadium. In an unforgettable showing, he smashed seven home runs in just three games, an achievement that remains legendary in Chicago softball history. That same year, he earned 3 MVP awards while playing across two teams and three leagues — further proof of his unmatched power and presence in the sport. In addition to his league and tournament play, Chip was a dedicated member of the RR Donnelley company softball team, serving as team captain each season. Off the field, he was equally committed to his work, remaining at RR Donnelley until his passing in 1999. Willie “Chip” Holmes leaves behind his daughter, Candra Holmes, and a legacy as a cherished athlete, leader, and beloved figure in Chicago’s softball community.
