Murals capture not only the scenes of Annapolis, but its backstories

A tour of Annapolis murals is great for the art, but even better when you know how to decode what’s behind the paint

Published 5/24/2023 5:30 a.m. EDT

“Proclaiming the Annapolis City Charter: 1708″ is the largest of the three paintings by Lee Boynton in City Council Chambers.

When Annapolis artist Jeff Huntington led 50 volunteers to create a massive portrait of Breonna Taylor, a 26-year-old woman shot and killed by police in her Louisville apartment during a botched drug raid in 2020, it made national news.

Painted over several days on the pavement of Chambers Park’s playground, the 7,000-square-foot mural is a tribute to the slain medical worker and the Black Lives Matter social movement that her death helped propel that summer.

It’s not hard to find, but a face the size of several playgrounds is best seen from the air, and it was a drone shot by Associated Press photographer Julio Cortez that was seen around the world.

From the ground, however, it’s hard to take it all in.

And then, wandering around this playground you come upon the eyes. They say something.

“No more.”

The eyes of Breonna Taylor are one of the features that have an impact on a human scale. The playground-sized portrait of the Louisville, Kentucky, victim of police violence is best seen from the air. But at ground level, elements have an impact.

Murals are part of what makes modern Annapolis such a charming city. You can spend hours admiring artists’ skill at weaving colors and shapes on a heroic scale.

Ah, but then there are the backstories. Behind the paint, you’ll find intrigue, shifting values and even one mural that influenced an election.

There are a thousand words behind every mural. Here are just a few of them.

Celebrating a tricentennial

In the early 1990s, Annapolis was ready to celebrate its tricentennial. What better way than to commission a mural of the moment?

Better yet, it’s a tricentennial, so why not three moments?

Then-Alderwoman Ellen Moyer convinced Mayor Dean Johnson and the rest of the City Council to hire Lee Boynton, one of the most successful Annapolis painters of his era. The city paid him $40,000 in 1994 to do the job.

The anniversary marked Gov. Francis Nicholson’s move of the state capital from St. Mary’s City to Annapolis in 1695, but Boynton’s central, largest painting was about something else: “Proclaiming the Annapolis City Charter: 1708.″ That’s when Gov. John Seymour presented the city with its royal charter allowing for local government.

That’s where the intrigue started.

Enslaved people feature in Lee Boyton's 1995 painting of the charter of Annapolis. About one-third- of colonists listed Black people as among their possessions at the time.

Some people loved it. So much so, that the city whipped up a 35-by-15-foot reproduction. It toured the area for years to public acclaim.

Critics though, led by historian Jean Russo, criticized the simplified, idyllic story portrayed in the paintings — despite Boyton’s year of research.

Yes, Annapolis got a charter. But 1708 also was the year that Seymour had planter Richard Clarke hanged for burning down the original state house in protest of the power shift from country to city. Enslaved men and women in the paintings look like they were having a great time. Plus, everyone looks like they just had a bath.

Mayor Josh Cohen set up a commission in 2013 to study the murals and had them shipped off with other paintings to the Maryland Hall for the Creative Arts during a renovation of the Council Chambers. But when the room reopened, dedicated to the city’s only Black mayor — Boynton’s murals were nowhere to be seen.

Moyer, who had gone on to serve two terms as mayor but was now out of office and involved with the Annapolis Art in Public Places Commission, pointed out that as custodian of the art works, the commission controlled their placement under city law. Cohen and the council relented, and back the murals came.

Today, they remain a backdrop to council deliberations. You can see them at City Hall, 160 Duke of Gloucester St., whenever the building is open.

A detail from “Proclaiming the Annapolis City Charter: 1708,″ the largest of the three paintings in City Council Chambers.

Great Wall of Eastport

Cindy Fletcher Holden grew up in Severna Park and made a living for years painting names on powerboats and sailboats. When fiberglass started to replace wood, though, demand for her craft began to decline.

So, she turned to murals as a sideline. Eventually, she would paint more than 20 murals around Annapolis, and decorate Starbucks locations during its expansion along the East Coast with unique details of local history and culture.

But her 1999 Eastport history mural may be her only work to vanish and be reborn.

Cindy Fletcher Holden's 2019 mural on Second Street celebrated the 150th anniversary of Eastport, and evoked an early neighborhood mural destroyed when the wall where it was painted fell down.

Hopkins Furniture on Main Street was in slow decline, and the company warehouse on Fourth Street in the Eastport neighborhood was fast becoming an eyesore.

Moyer, the alderwoman from Eastport at the time, approached Holden about painting a mural on it. The artist went to work on the 1,530-square-foot cinder block wall and painted some 30 boats designed, built, or famous in Eastport.

A champagne christening was held from the back of a pickup truck when it was completed, and the mural became a beloved landmark featuring a wide vista of the Severn River with Greenbury Point in the distance.

Then the wall fell down. The ruins were cleared away and eventually replaced with townhouses.

A section of Cindy Holden Fletcher's Eastport anniversary mural depicts sailboats against an orange sunset.

In 2019, Eastport celebrated its 150th anniversary and asked Holden to create a mural to mark the occasion — and evoke her original piece of community art.

The work, located behind a stretch of parking spots at the Spa Creek end of Second Street, can be hard to see in full. But on the rare occasion when there are no cars, it is a sweeping vista of what has gone into the neighborhood.

You can pick out boats, docks, the names of manufacturers long past, and that same, sweeping water vista.

Holden also recreated the style on a commercial building on Chinquapin Round Road at Margaret Avenue, the first of several murals in a multiblock area of businesses known as the Annapolis Design District.

Artists' signatures are something to look for during a tour of Annapolis murals.

Influencing votes

Huntington and Holden vie for the title of most prolific Annapolis muralist.

In addition to organizing and leading the Breonna Taylor mural, Huntington had created many other works around town, either by himself, with his wife and partner, Julia Gibb, or with his street art youth program, Future History Now.

He may also be the only artist to influence an Annapolis mayoral election.

“Agony and Ecstasy Live Together in Perfect Harmony” is a 20-by-50-foot mural in Annapolis that combines the peaceful expression of a golden Buddha with an injured nurse in agony from a 1925 silent film about the Russian Revolution. It also influenced an election for mayor in Annapolis.

Huntington’s spray paint creations play with perception, layering images and patterns, sometimes in opposition, to arrive at an emotion. When he started work in Annapolis, his style was not what you’d expect in a city where boat paintings dominate the art scene.

None is more provocative than his 2015 work, “Agony and Ecstasy Live Together in Perfect Harmony” above the restaurant Tsunami on West Street. The 20-by-50-foot mural combines the peaceful expression of a golden Buddha with a nurse in agony from a 1925 silent film about the Russian Revolution.

But the building is part of the Annapolis Historic District, and city preservation watchdogs said the mural didn’t have proper permits for such substantive changes to its historic character. City lawyers took the owners to court.

One of the owners was Gavin Buckley, soon to launch a sometimes irreverent campaign for mayor against incumbent Mike Pantelides. Buckley used the mural as a metaphor for what he characterized as Pantelides’ failure to move the city forward, a lack of balance between preservation and innovation. The Pantelides administration told him to just get a permit.

A judge sided with the city, saying municipal powers to approve building alterations were routine stuff and not an infringement of free speech. Buckley and his partners eventually applied for a permit, which was granted retroactively.

Buckley had the last laugh, winning in 2017 and again in 2021.

Jeff Huntington, who with his partner and wife Julia Gibb along with a youth street art group called Future History Now is responsible for a wide selection of Annapolis works, signs his art with @JAHRU.

What about George?

Why is there a mini Mount Rushmore in 2-D just off West Street? The portraits of Thomas Jefferson, Theodore Roosevelt and Abraham Lincoln mark the entrance to a neighborhood called — what else — Presidents Hill.

Portraits of Thomas Jefferson, Theodore Roosevelt and Abraham Lincoln are at the entrance to President's Hill on Madison Place.

And yes, all three spent time in the city. Maybe George Washington, who of course resigned his commission as commander-in-chief here in 1783, just didn’t fit?

Here’s a quick guide to some of the other faces gracing Annapolis murals.

Who’s that woman looking down from the back of a West Street parking lot next to Stan and Joe’s Saloon? It’s Eva Cassidy.

The Maryland singer frequently performed in Annapolis until her death from cancer at age 33 in 1996. Some of her songs were released in March with new, orchestral arrangements. The lot is occasionally cleared of cars and converted to the Eva Cassidy Songbird Lot for concerts and events.

Eva Cassidy, the late Maryland singer who frequently performed in Annapolis until her death from cancer at age 33 in 1996, remains a powerful figure for many.

So it’s not a surprise that she graces a parking lot on the first block of West Street, a part of town with plenty of music.

If you drive along Forest Drive, you’ll notice a unique mural. It’s the city’s only permanent — sort of — mural not attached to a building. It depicts a beloved Annapolis rapper named Tre Da Kid.

The portrait of Tre Da Kid, painted by Jeff Huntington, is located on Forest Drive near the spot where the Annapolis singer was killed in a drive-by shooting.

Edward Montre Seay grew up in Annapolis. He graduated from Annapolis High School while dreaming of making it big as a rapper under the name Trey Da Kid. Shortly after winning a national rap contest in 2019, he was killed in a drive-by shooting that police believe targeted another man in the car with him.

The mural near that spot has been repainted twice, most recently after someone defaced it by gluing an election campaign to his face.

Twentieth-century entertainer Pearl Bailey appeared in Annapolis during the hey-day of the city's once segregated Black neighborhood, The Old Fourth Ward. The mural marks the spot where the neighborhood once stood.

Why is there a mural of the late actress, singer and author Pearl Bailey in Annapolis? Located on the side of the Whitmore parking garage next to the People’s Park on Calvert Street, it marks a part of the city’s once-segregated neighborhood known as the Old Fourth Ward.

Bailey earned $20 a week performing at the Washington Hotel in the 1940s.

If there’s anything odd about a liquor store named Pinky’s, no one is saying anything about it in Annapolis. It’s a bright pink building at the corner of West Street and Linden Avenue — near the Thai restaurant that sells Carlson’s doughnuts. Or is it Carlson’s that sells Thai food?

On the side of Pinky’s is the face of Carlester Smith, a beloved figure in the community who was known to walk West Street vigorously swinging his arms and waving plastic trash bags while earning money cleaning up parking lots.

His family announced that he died in 2021, just after the mural by artist Comacell Brown was dedicated.

Known as The Walking Man during his lifetime in Annapolis, the late Carlester Smith is memorialized in a mural at Pinky's Liquors.

The Best Place

When Steuart Pittman was first elected county executive in 2018, he tweaked the Anne Arundel slogan adopted by his predecessor from “The Best Place to Live, Work and Start a Business” to “The Best Place for All.”

Slogans come and go with the change of administrations, but Pittman took it one step further.

"Best Place for All" on the side of the Arundel Center at 44 Calvert St. in Annapolis is a play on the county slogan chosen by County Executive Steuart Pittman.

The administration sponsored a contest to design and paint a mural for the unadorned side of the Arundel Center at 44 Calvert St. The theme: “Best Place for All.”

Rather than pick an artist, the county decided that two would be better — settling on Fletcher, who is white, and Brown, who is Black.

Fletcher and Brown split the $60,000 commission and collaborated over several weeks, spending hours on a lift together.

The original design was Fletcher’s, a landscape of familiar images — water, boats and birds. Brown introduced the people, some he knew and some he saw as a symbol of those who live in the county. The finished painting also included a self-portrait of the artists.

No one has said what might happen when the next county executive wants a different slogan.

"The Best Place for All" on the side of the Arundel Center at 44 Calvert St. in Annapolis includes a self-portrait of the artists, Cindy Fletcher Holden and Comacell Brown.

There are plenty of other murals worth touring.

There is the painting of the late Supreme Court Justices Thurgood Marshall and Ruth Bader Ginsburg by Gibb and Future History Now. It’s outside the county courthouse.

There is “The Waterman,” a vision in blue designed by Joe Karr. Located on Prince George’s Street, it’s a nod to the Burtis House. That 19th-century waterman’s home will be moved to serve as the center of the proposed Chesapeake National Recreation Area.

You can try any one of a number of tours of Annapolis murals. Two good places to start are at the city website and at Visit Annapolis.

Just remember to ask about their backstories.

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