R.I.P. Winfield M. Kelly, Jr., AKA Mr. Prince George’s

For many years, Winfield M. Kelly, Jr. was a newsmaker, a homegrown success story in then majority-white blue collar Prince George’s County, Md. abutting the District of Columbia. He was a county commissioner, then a county council chairman, county executive, Maryland secretary of state, CEO of the county’s healthcare system, and a self-made businessman who modestly began bringing food trucks (known as “Winnie wagons”) to construction sites throughout the county during its building boom years in the 1960s.  He was one of 14 children growing up in the streetcar suburb of Mount Rainier whose father drove a beer and soda truck for a living.

As a Washington Post reporter, I covered him. He died May 23 at the age of 87. The Washington Post paid him no mind. There was no obituary, not even a brief. Disappointed? Yes. Surprised? No. Nor would Winnie be. He was used to his county being slighted by the Washington elite.

As Winnie’s personal and political fortunes rose in what some referred to as Washington’s “ugly step-sister,” he refused to surrender to the snide barbs from the more affluent residents of DC and Montgomery County.  He bridled at the use in headlines of “P.G,”  noting that Prince William County, Va., for instance, was never referred to as “P.W.”   He tried to rename Montgomery County, home to the rich and famous, as “Monkey County,” but it never took.

A Democrat, he became known as “Mr. Prince George’s,” a title he wore proudly. As county executive from 1974 to 1978, he had working for him a stable of hard-charging young aides who included John Lally, my dial-a-quote source, and Wayne Curry, who would become the county’s first Black county executive as white flight led to a Black majority population.

Winnie’s goal as county executive was to elevate the county’s image and economic status by encouraging construction of more upscale residential and commercial developments. He called this his “New Quality” program, shortened to “the New Q.” But there were headwinds, which included a white backlash against court-ordered integration, leading to the creation of white “seg academies,” similar to those established in the South. Ironically, as the county became majority Black, and white families moved further out, the “seg” schools also became largely Black, perhaps out of economic necessity.

There was also a growing anti-tax movement that had famously begun with California’s Proposition 13, which migrated to Prince Georges” as TRIM, a property tax cap that inhibited county spending and programs. In 1978, Winnie ran for re-election, and lost.

The winning candidate was Lawrence J. Hogan, a former FBI agent and congressman who, as a member of the House Judiciary Committee, was the first Republican to support the impeachment of Richard M. Nixon.  Decades later, his son Larry Hogan, Jr., would serve two terms as governor and be widely portrayed as a moderate Republican critic of President Donald J. Trump.

My assignment during the 1978 campaign was to profile Hogan, while Winnie was assigned to David Maraniss, my friend and colleague who went on to become a Pulitzer Prize-winning author and associate editor of The Post.  Our approaches were quite different.  I used my investigative skills to do a deep dive into Hogan’s career; David wrote a prose poem about Winnie.  Our pieces were not, shall we say, aligned, and I had to do a rewrite to tone down Hogan’s rougher edges, or so it seemed to me. When my profile appeared, Hogan was greatly relieved and, thereafter, always and promptly answered my calls. I will say, now, I liked the guy.  When he and his wife moved from Prince George’s to Frederick County, I wrote about their new home for the paper.

Winnie, meanwhile, remained in the county, while serving as Secretary of State under the colorful Maryland Gov. William Donald Schaefer, and for 18 years as CEO helming Dimensions Healthcare, the nonprofit that ran the county’s large hospital system. He also enlarged his commercial ties and business interests, owning car dealerships and serving on many boards.

Then, in 2001, Mr. Prince George’s did the unthinkable.  At 65, he left the county. He and wife Barbara moved from a 7,300-square foot house on 2.5 acres in the gated Woodmore subdivision he’d helped to create to a 4,006-square foot contemporary home on 9.22 fenced acres 11 miles west of Prince George’s, near the tiny hamlet of Dayton in Howard County.

Most of his seven children had preceded him to Howard, where the family owned Win Kelly Chevrolet.  “He was one of the last dogs to die, so to speak,” Gerard T. McDonough, a former county council member and Woodmore resident who had also moved out of the county, told me. “Poignant, I guess, is the right word.”

Not quite three years later, I covered Winnie’s “retirement” from Dimensions, with more than 300 well wishers crowding a ballroom in Greenbelt, in Prince George’s. It was a class reunion, I wrote, “at which  the members were mostly older white men and women of a generation that has largely yielded political power in the county to younger, African American leaders.”  Joked Kelly, “I’m looking for work. I’m out of a job.” In a video prepared for the event, Christopher Kelly, one of his sons, said, “Just two dollars a day will keep him off the street. Dial 1-888-HIRE-DAD.”

By chance, I learned about Winnie’s passing from a former Post colleague who messaged me. She in turn had learned about it from a mailing list. She, too, had written about him, and there were clips. “I didn’t see anything in the Post…Winnie was very prominent for decades in Maryland and is certainly worthy of an obit.”   At a funeral mass on June 6, his son Ryan, 31, spoke briefly. For his father, he said, “It was never about ‘myself.’ It was always, ‘I’m here. What can I do to help?'”  U.S. Rep. Steny Hoyer (D-Md.), 84, like Winnie a graduate of a Prince George’s public high school, spoke longer about his “dear friend and good American.”  Watching the mass on YouTube, I counted only some 50 in attendance, plus perhaps eight family members seated in the front row.

Years after leaving office, in 1999, Winnie published a vanity book about himself, his company, family and career. It was called “Filled with Wonder: The Life of Winfield M. Kelly, Jr.”  I once had an inscribed copy. I no longer do. Recently, on Amazon, I found one “Used, Very Good” copy for $59.95, and another “collectible” copy “like new…in Near Fine condition” of the “Oversized Oblong Hardback with Dust Jacket” inscribed by Kelly to his “Long Time Friend,” Pete, with “Best Personal Regards… 9-8-2000. ” The  listed price was $13.45, plus $4.50 for shipping.

Rest in peace, Winfield M. Kelly, Jr.   At least you are remembered here.





  1. Craig Herndon on July 3, 2023 at 2:16 pm

    A gentleman and fun to be with.

  2. Emily Levenson on July 3, 2023 at 7:16 pm

    As the saying goes”they just don’t make them like that anymore”. You’re a good friend to remember him with such a lovely piece. Sorry for your loss of a friend

  3. Tom O'Reilly on July 5, 2023 at 6:10 pm

    Thank you for your very kind thoughts, Gene. All that you said of him is absolutely true.
    I was quite surprised to read of his passing today in Maryland Matters. Win was a very decent and very talented man. Whatever he undertook he gave 100%.
    We will keep him in our prayers for the repose of his immortal soul. May he rest in peace.

    • Anne MacKinnon-Welsh on July 8, 2023 at 5:24 pm

      When I was a 10th grader at Parkdale HS, Rob White (Francis White’s son) invited me to sit in his 12th grade government class to hear Winnie Kelly speak. A few minutes into his remarks, he stopped and pointed me out as a Democratic campaign volunteer and apologized for not knowing my name. After I said my name, he promised he’d never forget it. He never did. He had a way of making everyday people feel special throughout his accomplished life. Thank you for recognizing one of Prince George’s most treasured leaders.

  4. Diane Mothershead Montgomery on March 9, 2024 at 10:12 pm

    Winnie, rest in peace. You were a kind, thoughtful friend. You did so much for our county.

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