James Michael Sullivan, affectionately known as “Pirate,” died of a massive heart attack on October 29, 2018 at the age of 61. It was an ironic event given he was a man with a massive heart of generosity, compassion, kindness and love. He was born in Holyoke to the late Edward J. and Phyllis F. (Moriarty) Sullivan. He attended Blessed Sacrament School and was a member of the class of 1975 at Holyoke Catholic High. He graduated from Westfield State College, then launched a stellar career in teaching and mentoring that lasted just over 30 years. He retired from the Holyoke School system in 2017, leaving a legacy of having given his students the gift of learning and life skills in critical thinking, and teachers and administration an example of how to fight and stand up for justice while never degrading the humanity of anyone with differing opinions. He was a man of service and served his country in the U.S. Navy and proudly served the teachers of Holyoke as President of the Holyoke Teachers Association. Along with all of Holyoke, the city that he loved, who mourn this loyal son, he leaves his nephew Augustin Edward Ortegas with whom he shared a love of sports, each having an uncanny mind for sports trivia; his niece Nora Celena Ortegas with whom he shared a special bond with their love of music. He loved them both as though they were his own children. He leaves his sister Joanne Sullivan Ortegas of West Springfield and his sister and brother-in-law Ellen and Norm Atwood of Gales Ferry, CT; a large extended family of aunts and cousins; and an incalculable number of friends and colleagues with many “Pirate” stories that will be told for years. All are invited to Barry J. Farrell Funeral Home, 2049 Northampton Street, on Friday from 3:00-7:00 p.m. where we can joyfully reminisce how Jim impacted our lives. There will be a funeral Mass at Blessed Sacrament Church Saturday at 10:00 a.m. meeting at Farrell’s at 9:00. If you care to, in lieu of flowers, you may make a donation to the Sisters of St. Joseph Retirement Fund, 577 Carew Street, Springfield MA 01104.