Alexander Whiteside

August 29, 1944 - May 16, 2023

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Obituary for Alexander Whiteside

Alexander Whiteside, 78, of Hillside St. passed away peacefully, surrounded by his beloved family.

He is survived by daughter Margaret Whiteside of Boston and son Alexander Whiteside Jr, of Milton, as well as sister Haidee Flinders, nephews Matthew and Andrew Flinders, and his constant companion, Gremlin.

Alex spent his childhood in Milton with his two sisters, Haidee, and Lisa (who predeceased Alex in 1999) and their parents Howard Whiteside and Elizabeth (Swift) Whiteside. Alex graduated from Harvard University with a degree in history before receiving his law degree at Fordham University and eventually earning a Masters in Law from Boston University.

After years of private practice, including working alongside his father Howard Whiteside with the firm of Putnum, Bell, and Russell, Alex entered the public sector. He was appointed by Governor William Weld to the position of Chief Counsel to the Massachusetts Department of Housing and Community Development, where he remained for 16 years. Though his contributions to State government were significant, it is to the town of Milton that Alex made his most indelible mark during his life of public service.

A Town Meeting member of long standing, Alex’s greatest contribution to the town certainly came as a member of the Milton Planning Board, of which he was an integral member and frequent chairman for over 30 years. With his mastery of the forms and peculiar linguistics of zoning law, and deep attention both to the details and coherency of legal writing, Alex almost always had a hand (more often both hands and a foot or two) in the drafting of any zoning of note. One could say that he shaped the town itself by defining the parameters on which its myriad constructions were built. Even after his tenure as Chairman of the Planning Board ended, he continued to provide time, energy, and legal knowledge to the town, using his influence as a Town Meeting member and private citizen to make vital contributions to issues ranging from the new high school to senior housing, about which he penned the recent successful ballot initiative.

A man of honesty, integrity, and indefatigability, Alex reached the apex of his political influence when most would have left town politics behind. At the time of his death, he had just finished a proposal to ameliorate the carnage and confusion wreaked by RT 28’s infamous traffic light.

With a wry wit and an unflagging loyalty to friends and loved ones, Alex will always be fondly remembered by those who knew him not only for his keen sense of justice, but the compassionate and loving nature barely concealed beneath a stoic façade. He was active until his last day, running with his dog, Gremlin, chopping brush, performing acts of household maintenance better left to professionals, never losing the strength and endurance for which he was so widely admired.

Visiting hours at Dolan Funeral Home, 460 Granite Avenue, EAST MILTON SQUARE, Thursday June 1st from 2-4 PM. Family and friends invited. Burial will be private.

A memorial service will be held at St Michael’s Episcopal Church, 112 Randolph Avenue, Milton, MA 02186 at a later date.

Services

1 Jun

Visiting Hours

02:00 PM - 04:00 PM

Dolan Funeral Homes and Cremation Services - EAST MILTON SQUARE 460 Granite Avenue Milton, MA 02186 Get Directions »
by Obituary Assistant

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Condolences

  • March 08, 2024

    After my wife and I left Whitinsville to take up residence in DC, OUR contact with Alex, centered around Memorial Day and remembering his Whitinsville relatives. His loyalty to his industrious Whitin family ancestors was remarkable. Alex devotion to his mother Betty, and his Aunt Priscilla, in their aging years was admirable. May he rest in peace.

  • June 25, 2023

    Alex was a formidable bridge player: I always wanted to be his partner for we never lost. I think his wry wit confused our opponents who, often in fits of laughter, would renege or forget their bid. My deepest sympathy extends to his two children Zack and Mollie, both of whom I have known and followed their continued successes over the years. Phil Clendenning

  • June 06, 2023

    We met Alex at our antique shop quite a few years ago. When he was in Wareham, he always stopped after doing his dump run. He became a frequent visitor and a good friend. He was always with his dog Yaz, until Yaz passed, and then he came in alone. He bought one of our old cars and we enjoyed seeing him driving it. Alex was an interesting, soft spoken, gentle individual. He became a good friend to all of us. Everyone at Marion Antiques will miss him. Frank, Diane, Peter, and Abby

  • June 02, 2023

    I had tremendous admiration for Alex and his innumerable contributions to Milton and to our neighborhood. He will always be missed. My deepest condolences to his family. Claudia Clifford

  • May 29, 2023

    I am already missing our frequent lunches at La Scala in Randolph. Alex was a steadfast friend with a quirky sense of humor that I loved. Mary and I send our condolences to his family. Ted Wendell

  • May 26, 2023

    Alex was welcoming, knowledgeable and kind when we moved into the neighborhood, Alex was a huge asset in our community and we will feel his loss. We send his son and family our best wishes. If there is anything you need, please know we are here. the McGrath family

  • May 25, 2023

    What I most frequently hear Miltonians say of Alex's passing is that it is "a great loss." Both in and out of office, Alex was outstanding, steadfast and selfless in his many contributions to Milton and the state of Massachusetts. He wanted the town to follow the law and to do what was right. He devoted endless hours to help pursue those aims and contributed the highest level of legal knowledge and expertise. He also mentored others to encourage good citizenship, which is always sorely needed. Carol Stocker

  • May 23, 2023

    Alex was a force of nature, who truly loved Milton, the character of the town and most importantly the people, hard to believe he is gone. RIP Alex thank you for a life well lived

  • May 22, 2023

    Alex was a dedicated citizen and public servant to the Town of Milton. His contributions are many. I had great respect for Alex and was fortunate to get to know him years ago while working on neighborhood advocacy issues in Milton. His expert opinions and thoughtful strategizing were something to count on. I just had a nice conversation with him outside the last town meeting. I was surprised to get word of his sudden passing. Alex will be missed.

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