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Carlester Smith, the Annapolis ‘Walking Man,’ has died at age 63

Carlester Smith, known to a generation of Annapolis residents as “The Walking Man” from years of waving at passersby and flashing a bright smile as he picked up trash on daily speedwalks, died Monday at age 63.

For years, Smith, who went by many nicknames, was a staple along West Street. With trash bags tucked into his pants, he cleaned parking lots and washed windows, earning himself some money.

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While he often didn’t make conversation, he smiled and yelled at cars and pedestrians as he waved plastic bags. A few years ago, he stopped walking after suffering a few falls and was taken into the full-time care of his sister Rosemary Graves. He lived with her for his final years in Glen Burnie.

That is where “Uncle Lessie,” as his family called him, died peacefully on Monday, said Janell Johnson, Smith’s niece.

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As news of his death spread, condolences poured in from the greater Annapolis community, including Mayor Gavin Buckley and members of the City Council. A Facebook page dedicated to Smith with more than 13,000 followers was flooded with photos, memories and well-wishes.

“One of the things that we knew for certain about him, and just our community, is that he was loved,” Johnson said.

Smith was born in May 1957 in Arnold to his parents Charles and Evelyn Smith, one of eight children.

After a fire displaced them, the family moved to Annapolis. The story goes that Charles Smith met with Annapolis Mayor Roger “Pip” Moyer, who helped them secure a new home in Obery Court where Carlester Smith was raised, Johnson said.

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Alderwoman Rhonda Pindell Charles, D-Ward 3, recalled growing up with Smith’s family in the Parole community, including attending Parole Elementary School together.

“Carlester’s passing is a terrible loss to our community. In these times of divisiveness — nationally and locally, Carlester was literally a walking example of how we should appreciate each other — a daily reminder of who we should be and how we should contribute to the positive quality of life for everyone,” Pindell Charles said.

Smith attended school until the sixth grade and was then placed in a vocational institute before he worked for years as a janitor at what was then the Parole Holiday Inn, according to a 2005 article in The Capital.

As a youngster, Smith participated in the Maryland Special Olympics, competing in track events and bowling. His parents’ home was filled with medals, trophies and certificates from his athletic achievements, his niece said. He also played basketball at the Stanton Center and was an honorary member of the Tommy-Tom Marching band, who he would march with during city parades, she said.

After his parents died in the mid-1980s, Smith, who was developmentally disabled, was cared for by his sister Roberta Smith. When she died about a decade ago, Smith went to live with his sister Rosemary Graves.

Looking back, Johnson was amazed by her family coming together to make sure Smith’s needs were always met.

“There was never a discussion of, ‘OK, who is going to take Lessie?’ When I think back to the way that they all adjusted their personal lives without an argument, without thought, to make sure that their brother was safe, it takes my breath away,” Johnson said. “In 40 years, he never knew void, or want or abandonment. He was loved and protected, and they went above and beyond to make sure of that.”

When new hotel managers fired Smith, he began to speedwalk up and down West Street, arms swinging, always grinning. Bill Malley, co-owner of Pinkey’s West Street Liquors, recalled first seeing Smith when the store owner moved to the area in 1983 and thinking, “Who is this guy?”

As he got to know Smith, Malley found him kind and generous, always willing to help.

“He was just the sweetest guy. He would always ask how you’re doing and if you needed anything done, anything he can do for you,” Malley said. “He never asked for anything for himself.”

For more than two decades, Smith went about his daily power-walks uninterrupted. But that changed in 2005 when Smith was stopped by a state trooper not familiar with the Annapolis walking man. Smith was pinned to the ground in the altercation that followed and was later transferred to a nearby hospital. Charges were dropped following a community outcry.

As the years went on, the scant facts of Smith’s personal life mixed with legend, egged on perhaps by the nature of word-of-mouth storytelling and further distorted by books, like “Weird Maryland,” a travel guide full of quirky — though potentially dubious — tidbits about the state’s history. The book showed a picture of Smith, though it does not include his real name, and claimed he was a millionaire who had donated a fortune to charity and was struck by a car, leaving him “deaf and disoriented.”

None of that is true, his family said.

“The only treasure he had was an internal innocence that was protected by his family and the entire community of Annapolis,” Johnson said. “To me, that’s as priceless as it gets.”

Governor Larry Hogan gave Carlester Smith a Governor's Citation.
Governor Larry Hogan gave Carlester Smith a Governor's Citation. (Paul W. Gillespie/Capital Gazette)

Last summer, Smith was honored with a citation from Gov. Larry Hogan’s office for his “legendary reputation as a fast-walking, arm-waving, always smiling beloved Annapolis icon who has been devoted to keeping the streets clean.”

Buckley said the city is planning to hold a citywide clean-up in his honor when it’s safe to do so.

“We are sad to hear the news about Carlester’s passing, but we are grateful for the legacy of kindness he has left our city,” he said.

In July, Annapolis artist Comacell Brown and others painted a mural of Smith on the side of Pinkey’s West Street Liquors, where he bought sodas after cleaning the parking lot.

“I have seen Carlester my whole life, and as I grew up, I protected him and told others about his story,” Brown said at the time.

Smith is preceded in death by his parents Charles and Evelyn Smith, sister Roberta Smith, and brother, Michael Smith.

He is survived by his siblings, Rosemary Graves, Robert Smith, Charles Samuel Smith, Brenda Williams and Rhonda Gross; his nieces Janell Johnson and Rosie Godard-Grant, and many nieces and nephews.

Private funeral services have not yet been scheduled as Smith’s family is still processing his loss, though a public tribute or memorial service to celebrate his life may be forthcoming, his niece said.

“To the Annapolis community, thank you for loving him as your own son,” Johnson wrote in a Facebook post. “We never really had to worry about him much, not with so many incredible guardian angels. What an amazing place to be from!”

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