James Francis McEneaney Jr.

James Francis McEneaney, Jr. - "Jim(my)" to some, "Mac" to others, and "Grumps" to his 13 beloved grandchildren - left this world peacefully on Thursday afternoon, July 31, 2025, at Discovery Village Senior Living Community in Stuart, FL
Born June 25, 1938, in Philadelphia to the late Carmel and James Sr., Jim got an early start on romance - he and the love of his life, Agnes "Tudie" Walsh, spent their very first years of life as next-door neighbors. His family later moved to Cleveland, where he graduated from St. Ignatius High School, became the first in his family to attend college, and put himself through Baldwin-Wallace while working full time on the 3rd shift at the Firestone plant. Somewhere in between, he rekindled his connection with Tudie, and in July 1960, they married - beginning a 65-year union built on true partnership, mutual respect, and a love story equal parts devotion, banter, and adventure.
Jim began his career in computer sales at Honeywell Systems. In 1973 he shifted gears, joining Crest Communities (later Ryland Homes) and launching a wildly successful career in residential construction. His four children were often - and incorrectly - called "military brats," thanks to the family's frequent moves across Ohio and Indiana throughout the '70s and '80s. In 1981, they settled in Annapolis, MD, where Jim rose to President of Ryland Homes before retiring in 1994.
His career was as impressive as it was involved, filled with boardrooms, job sites, and more than a few legendary deals - each of which he could recount in a story long enough to require an intermission. In the spirit of efficiency (which he would appreciate in theory, if not in practice), we'll keep it short and just say he was as commanding in the boardroom as he was relaxed on the tailgate of a pickup truck, beer in hand - his version of "field management."
A pillar of the Annapolis community for over three decades, Jim served in leadership roles with the Annapolis Yacht Club, on the board of Anne Arundel Medical Center, and with the Board of Visitors at the University of Maryland's Robert H. Smith School of Business. A man of deep faith, he was also active at St. Mary's Catholic Church, where he and Tudie renewed their wedding vows in 2010. He embraced boating with the same gusto he brought to his career, creating lasting memories for his family at the Severn River home he designed himself.
In the early 2000s, he and Tudie began wintering in Florida, eventually making Hobe Sound their full-time home in 2017, where they built a "second family" of treasured friends through their neighborhood and on the golf course.
The family is profoundly grateful to Jim's sister Kathy, who moved from Oregon to be by his side in his last few years, and to his devoted caregivers, the compassionate staff at Discovery Village, and the many friends at Lost Lake whose love, laughter, and unwavering support carried him - and all of us - through.
Jim was briefly survived by his beloved wife, Tudie - his partner of 65 years and his steadfast caregiver through much of his illness. Just a month later, on September 2, 2025, she soon followed him, their love proving stronger than even time itself. It feels only fitting that they are together again, given the lifetime love story they shared.
He is survived by his sisters Toni and Kathy; children Lisa (Barry), Mark (Robyn), Trish (Rick), and Matt (Flo); his 13 grandchildren (many with partners of their own); and his great-granddaughter, Caroline, who dubbed him "Mr. Grumps." Each one of them was fiercely loved by him, even if his version of affection sometimes included unsolicited advice and a very specific way of doing things "the right way" (i.e., his way).
Joint celebrations of Jim and Tudie's lives will be held at a later date in both Hobe Sound and Annapolis. Jim was a force who left his mark on countless people. For most of his life, he had an impeccable memory and could recall every detail. Alzheimer's - a cruel and relentless disease - took that from us in the end. He faced it with the same dignity, courage, humor, and stubborn determination that defined his life. We encourage donations to Treasure Coast Hospice in his name. His memories and stories live on through all of us, and we'll keep telling them for years to come - though probably not for quite as long as he would have.