Judge James J. “Jim” Stapleton, of Holyoke, MA and Naples, FL, died peacefully at home on Monday, surrounded by family and friends. He was born in Holyoke on March 29, 1930, the youngest of five children of the late Edward J. and Agnes (Kidnay) Stapleton. Jim graduated from Holyoke High School, the University of Massachusetts at Amherst, and Boston University School of Law, where he obtained a Juris Doctor degree. He served as a First Lieutenant in the Judge Advocate General Corps stationed at the Headquarters of the U. S. Army in Heidelberg, Germany, and later was appointed as Prosecutor for General Courts Martial trials in Germany, England, and France. Upon honorable discharge from military service, he worked as a trial attorney with a law firm in Worcester, MA from 1957 to 1961. In 1961 Jim was hired by Ted Kennedy to assist in Ted’s first run for the U. S. Senate to fill the seat vacated by John F. Kennedy who was newly elected President. During the campaign, at Ted’s invitation, he resided at President Kennedy’s apartment in Boston. Following Senator Kennedy’s election to the Senate in 1962, Jim was appointed Executive Assistant to the Assistant Postmaster General and served as Presidential Advance Man during the Kennedy and Johnson presidencies. He later served as Executive Assistant to Senator Daniel Brewster of Maryland, and then as Assistant Chief Counsel of the Federal Highway Administration and Executive Director of the National Motor Carrier Advisory Committee. During the years he worked in Washington, Jim resided in Bowie, Maryland, where he served as a member of the Bowie City Council. In 1986 Jim was appointed as a United States Federal Judge where he served in Springfield, MA as the Chief Judge until his retirement at the beginning of 1996. In 1999, he went into private practice with his nephew, Attorney Edward Stapleton, and continued to actively consult on cases for Stapleton Law Offices into his 80’s. He was inducted into the inaugural class of the Holyoke High School Hall of Fame and was a proud member of the B & B Club. Jim loved to make people laugh. During his years in Washington, he played the leading role in many dinner theater productions, including The Solid Gold Cadillac, Cactus Flower, Lovers and Other Strangers, Prisoner of 2nd Avenue, and Never Too Late. Jim’s favorite role was as Oscar Madison in The Odd Couple. Jim, who loved God, his wife Louise, his family, the sound of laughter, and life itself, is now safely in the arms of the Lord. He will be missed as an uncle, great uncle and friend. Jim was predeceased by the love of his life, Louise R. Stapleton, to whom he was married for 68 wonderful years. He was also predeceased by his brother, Father Edward J. Stapleton, S.S.E.; sister, Lorraine M. Stapleton; brother, Attorney William F. Stapleton; sister, Frances S. Millane, sister-in-law Attorney Lillian F. Stapleton, and brother-in-law Jeremiah J. Millane. Jim is survived by several nieces, nephews, grandnieces and grandnephews. He is also survived by his sister-in-law Deborah McLaughlin of Holyoke. Jim particularly wanted to acknowledge the loving support and friendship from his two best friends and caregivers, Katie and Kristy. Also, he was grateful for his wonderful caregivers Valerie, Michelle, Manar, and Shaday. Calling hours will be held at the Barry J. Farrell funeral Home, 2049 Northampton Street, Holyoke, on Friday, January 31st from 8:30 to 10:30 AM. A Mass of Christian Burial will be held at Our Lady of the Cross Church, Holy Cross Avenue, on Friday January 31st, at 11:00. Burial with military honors will be held the following day, Saturday February 1 at 10:00am in Saint Jerome Cemetery, 1666 Northampton Street, Holyoke. In lieu of flowers, donations may be made in Jim’s memory to Food For The Poor, P.O. Box 979005, Coconut Creek, FL 33097, or to a charity of one’s choice.