Joseph Anthony Calareso passed away peacefully on April 28, 2024, surrounded by his family with love, laughter, cannolis, and prayer. He is survived by his wife of 53 years, Stephanie, and their daughters, Christine Bleecker, Angelina Weyler, Dianna Sawyer, and JulieAnne Calareso; his sons-in-law David Bleecker, Rand Weyler, and Kevin Sawyer, as well as his beloved grandchildren: Benjamin and Joseph Bleecker; Sydney, Reagan, and Piper Weyler; and Jolene and Penelope Sawyer. He is also survived by many nieces and nephews. Joe is predeceased by his parents, John and Anna Calareso, his brother, Jimmy Calareso, his nephew, Johnny Calareso, and his son, John Stephen Calareso.
Joe grew up in Hyde Park, MA, where he attended The Roxbury Latin School and later Bowdoin College in Brunswick, ME. An athlete, scholar, and lover of practical jokes, Joe made lifelong friends at both schools, modeling for his family the value of deep, abiding friendship. He met Stephanie while working at the P. Tavilla Produce Company in Boston; despite being told not to approach the boss’s daughter, Joe persisted and the two married in 1970, enjoying a strong marriage defined by mutual love and support. Joe made Stephanie laugh every day, and spent his entire life expressing his love and unwavering devotion to her. After the death of their infant son in 1975, Joe established the John Stephen Scholarship Fund at Roxbury Latin. The Fund provides a full scholarship for young men who have exceptional potential but would otherwise lack the ability to attend Roxbury Latin; receiving the updates on these scholars was a source of joy for the entire Calareso family. Joe and Stephanie went on to have four devoted daughters, who were the light of Joe’s life. He loved nothing more than cheering them on at volleyball and soccer games, band concerts, and graduations. He loved seeing his grandchildren grow into their own talents; Grampy beamed with pride as his grandchildren excelled at football, baseball, music, art, and theater. He delighted in spending time with his grandchildren—eating ice cream, riding on the golf cart, and watching baseball together on the couch.
Joe instilled in his daughters the importance of faith; it gave him tremendous joy to see all of his children and grandchildren following God in their own lives. He was an active member of every church he attended, always involving himself in acts of community service and generosity. His heart and hands were always open wide, drawing people to him with his quick wit, intelligence, and eagerness to give. Good luck paying the bill at a restaurant with Joe; he loved seeing a table full of people eating, laughing, and enjoying life together.
Sports were a major part of Joe’s life, from his days on the baseball diamond and football field, to attending countless MLB, NFL, and NBA games. His biggest passion was baseball, and he could often be found cheering on the Red Sox and taking his daughters to nearly every Marlins home game; he enjoyed teaching them how to keep score and shouting “can o’ corn!” at every pop fly. Joe loved the competition of sports, but he also took very seriously the values of teamwork, sportsmanship, and practice. He encouraged his daughters to set goals and work hard to achieve them; he was supportive in all their endeavors and often shared life advice through the lens of sports, including his favorite: “When you get to the end zone, act like you’ve been there before.”
Joe expressed his love through humor and acts of service. He prided himself on keeping the gas tank full, preloading Dunkin’ Donuts gift cards for his kids and grandchildren, and being known as the most reliable person to call for an airport pickup. He drew people in by making them laugh, and disarmed them by being able to laugh at himself. Despite his profound intelligence, he loved to be silly, making up songs, expressions, and traditions that made his daughters laugh and roll their eyes. They have continued to teach their children some of Joe’s original vocabulary, like “budinski,” “scrubini,” and “grande salami.”
Despite having his own children, Joe was a father figure to dozens of others; his daughters have many friends who have expressed that Joe was the dad they wished they’d had. Joe loved having his daughters’ friends to the house, boiling lobsters for dinner (after racing them on the kitchen floor), flipping pancakes for breakfast, and encouraging everyone to watch his favorite movies, “Rudy” and “The Godfather.” Since Joe’s death, the family has received countless messages from people recounting their favorite memories of Joe; these memories include ways he made them laugh, ways he listened to and supported them, and how he made people feel at home.
Joe and Stephanie moved to southern Florida shortly after their marriage, and lived there until 2023 when Joe retired from a decades-long career in sales. They relocated to the Villages, where Joe discovered new passions such as water volleyball, ukelele, and U.S. and world history clubs. He loved living in the Villages and took advantage of every opportunity to make new friends, take up new hobbies, and enjoy live music and shows. He was a beloved member of multiple community groups, and will be missed by all.
A service to mourn the loss and celebrate the life of Joe will be held on Saturday, May 11, at 1 p.m., at Live Oaks Community Church Woodridge campus (12070 County Rd 103, Oxford, FL) followed by a reception at the Laurel Manor recreation center in the Villages (1985 Laurel Manor Dr, The Villages, FL).
