Richard Di Pietro, 68, a 16-year resident of Olney and previously of Silver Spring and Edgewater, MD, passed away at his home on April 3, 2021 following a 4-year battle with cancer. Born on July 8, 1952 in Hyattsville, MD to the late Enrico J. and Mary Frances Di Pietro, Richard graduated from Southern High School and attended Anne Arundel Community College, where he excelled athletically. He was the owner of Association Management, a home improvement company that specialized in roofing. Association Management would proudly serve the DMV for over 30 years, providing jobs for hundreds of individuals while regularly receiving accolades and being named as Washingtonian’s best roofing company. With a bigger-than-life personality, Richard filled every room he entered. He was an avid golfer, winning several awards including first place in the 1991 World Amateur Handicap Championship. He also enjoyed a good game of chess, playing poker and visiting Las Vegas casinos. One of his greatest pastimes was horseracing. His passion for horseracing can be traced back to the pages of Sports Illustrated where Richard can be seen on the rail at Pimlico Racetrack as legendary Secretariat won the second leg of the Triple Crown. He loved betting on horses and held the largest, single winning ticket in the history of Maryland horseracing. But that wasn’t his greatest racetrack win; it was meeting his wife, Jennifer, at the Laurel Racetrack. They were introduced by her father, Jimmy Leonard. Richard tucked a winning ticket under Jennifer’s dinner plate and that was the beginning of the romance. As much as Richard enjoyed all these interests, his greatest passion was his family and spending time with his children and grandchildren. Richard is survived by his wife of 26 years, Jennifer Di Pietro; five children, Richard A. Di Pietro, Rachel (Jay) Zelaya, Dominic R. (Samantha) Di Pietro, Richard Di Pietro II (fiancée, Renata) and Jennifer N. (Khalid) Di Pietro. He is also survived by three grandsons, Maddox, Aiden and Ragni and was looking forward to the birth of his granddaughter later this year. Friends are invited to celebrate Richard’s life with his family from 2 to 5 p.m. on Sunday, April 11 at the Kalas Funeral Home & Crematory, 2973 Solomons Island Road, Edgewater, MD. Mass will be offered at 10:30 a.m. on Monday, April 12 at St. John Neumann Catholic Church, 620 N. Bestgate Road, Annapolis, MD, with a luncheon to follow at Adam’s Grille & Taphouse in Edgewater, MD. Richard was dedicated to children excelling in life through sports. For those unable to attend the visitation, it can be viewed through the Zoom information below (Please remember to keep your microphones on mute): The Visitation of Richard DiPietro Meeting ID: 958 3945 3281 Passcode: 120769 In lieu of flowers, donations may be made to Wrestling to Beat The Streets DC