Robert Stirling Wylie III

The world lost some of its warmth and light on May 15, 2025, when Robert Stirling Wylie, III ("Rob" or "Bear" to most, and "Dad" to the lucky two) of Weston, Connecticut, wrapped up his six-year standoff with Stage IV lung cancer. It was a tie, by the way. Cancer might have taken his breath, but it never touched his spirit-the same buoyantly optimistic, kind, joyful soul we all adored and marveled at. Right up until the final round, Rob was still completely, wholly himself.
Rob was welcomed into the world in Manhattan, New York, in 1958 by his two loving parents, Robert S. Wylie, Jr. and Karen Berthelsen Wylie, and quickly made himself at home. Raised in Greenwich with his three younger siblings, his early years were a blur of cannonballs into the Long Island Sound from the family camp in Stony Brook, late-night pranks, meeting some of his oldest and dearest friends for the first time, and practicing the grin he would keep his whole life.
He studied history at Wesleyan University, rowed on the crew team, and joined Delta Tau Delta fraternity. After graduating, Rob spent a memorable summer working at a cannery in Alaska under the biggest star-laden sky he had ever seen before hitchhiking down to San Francisco. A J.D. from the University of Connecticut School of Law followed in 1984, and then-because why not-an LL.M. in Taxation from New York University School of Law in 1994.
He started in tax accounting at Arthur Andersen and then moved through United Technologies and PerkinElmer, where he became Vice President of Tax. Rob went on to become Vice President, Chief Tax Officer at Terex Corporation for sixteen years, where he managed a team of more than sixty attorneys, accountants, and tax professionals across five continents. He was proud of his work, and even more, he loved the people he did it with (even during quarter close).
And then there was Jane. He met her at her twentieth birthday party in London and instantly decided life would be better with her in it. They married in 1985 in Chalfont Saint Peter and spent the next thirty years raising their daughters Sarah and Meaghan, globe-trotting, living in Higganum, then Singapore, then Holliston, then Weston; skiing in Beaver Creek; snorkeling in Hawaii; gardening at home; helping the girls with their homework; and cheerleading them through good and bad days, college move-in days, and new job offers.
Though the location changed, some things stayed the same: Rob never stopped reading Stephen King novels or listening to the Grateful Dead too loudly and too often, and Jane never stopped teasing him about both. In 2020, Jane left this world before she should have, and Rob never stopped loving her-but he carried that love forward with grace, grit, and a deep devotion to their daughters.
After Jane passed, Rob continued to build joy into the world. He found adventure in quieter moments. He focused on becoming as healthy as possible for his family. He opened his heart again, sharing three wonderful years with his loving companion, Teri Gaberman.
We wish we had endless time with our Rob, but we still feel him here-grinning, grateful, full of light-telling us, "and in the end, the love you take, is equal to the love you make."
He is survived by his daughters, Sarah Wylie and Meaghan Wylie; his mother, Karen Wylie; his beloved siblings, Liza Thorsby (and Peter), James Wylie (and Donna), and Ian Wylie (and Pilar); and a big extended cast of nieces, nephews, in-laws, cousins, and lifelong friends. He is also survived by Pat Kelly, his late wife Jane's mother, whom he loved deeply. He is predeceased by his father, Robert, Jr., who passed away in January, and of course, by Jane.
A memorial service celebrating Rob will be held at Norfield Congregational Church, 64 Norfield Road, Weston, CT, on June 21, 2025, at 11:00 a.m. In lieu of flowers, contributions can be made in Rob's honor to The Robert S. Wylie, III "Closer to Free Fund" Campaign, supporting advances in cancer research at Yale-New Haven Smilow Cancer Hospital. To the Yale-New Haven Thoracic Oncology Team, who gave Rob not just more time but good time- thank you for more birthday parties, new seasons of Stranger Things to watch together, another Yankees game, and much laughter. We are forever grateful.