The Legacy of Legacy Day

Bill Leary • August 1, 2023


On the evening of August 16, 2014, nearly 1,500 partygoers gathered in Chestertown to inaugurate Legacy Day.

 

They cheered the floats, classic cars, and community groups that paraded on High Street; danced to the music of Quiet Fire (including Kent County native Jasper Hackett) and the recorded oldies played by DJ Stansbury; savored the soul food offered by vendors; and caught up with old friends.

 

They also came to honor entrepreneur and civic leader Charlie Graves, whose Uptown Club had showcased such giants of jazz and rhythm and blues as Louis Armstrong, Otis Redding, Ray Charles, Fats Domino, and Sam Cooke. Several attendees commented that Legacy Day 2014 was the most diverse gathering they could remember in Kent County. Then-Mayor Chris Cerino said, “We need to do this every year.”

 

Legacy Day 2023 marks the 10th anniversary of our annual celebration of the history and culture of Kent County’s African American citizens. In recognition of this milestone, Legacy Day 2023 is taking a retrospective look at the celebrations of the past decade that have expanded from a Saturday night dance party to a weekend of partying and education. We also recall the historic contributions of the African American community in music, business, education, religion, sports, and the military. 

 

The first Legacy Day was proposed by a community history committee in the Historical Society of Kent County (Airlee Ringgold Johnson, Jeanette Sherbondy, George Shivers, and Bill Leary) to figure out how to direct attention to the largely ignored history and culture of the African American citizens of Kent County.

 

As Legacy Day’s scope of activities has expanded in the past decade, the original goals and expectations have stayed constant. Legacy Day should increase the awareness and appreciation by Kent County’s Black and White citizens of their shared history and culture, and provide a good time with good music and good food. All activities should be free and open to all. And even if the August heat becomes uncomfortable, it should never rain on Legacy Day!                                                                                                                     

Legacy Day 2015 continued to explore the important role of music in African American life by recognizing local music venues and Kent County musicians from the 1960s and 1970s. The venues included four beer gardens in the 300 block of Cannon Street that offered rhythm and blues via the jukebox. In addition to the Uptown Club, the Concrete Club near Great Oak, also owned by Charlie Graves, and the Rank Poison Inn in Butlertown, later renamed the Blue Moon Tavern, featured live music. The best remembered local musician was saxophonist and singer Randolph “Jazz” Johnson; others were the Highlanders, the Rotations, the New Breed, and Black Soul. 

 

Legacy Day 2016 paid tribute to Black business owners of the 19th and 20th centuries. Successful 19th century entrepreneurs included restaurateurs Samuel and William Perkins, Levi Rogers, siblings Kitty and Thomas Toomey, and Henry and Louisa Harris; butcher and grocer James Jones; and real estate operator Thomas Cuff. In the mid-20th century, commercial activity flourished on Calvert and Cannon streets. Calvert Street was home to the Uptown Club, the Munson family store, and the Kenneth Walley funeral home. Cannon Street included three barbershops, two beauty parlors, four beer gardens, and the first Black electrician’s store.

 

Legacy Day 2017 honored 32 African American educators who taught or served as principals in segregated Kent County schools and later, in most cases, in integrated schools. A consistent theme of their recollections was that despite many discriminatory aspects of segregated schools, Black students received a quality education before the long-delayed integration of Kent County schools in 1967. They attributed that success to well-prepared and committed teachers, strong leadership that enforced high academic standards and discipline, and strong support from the African American community.

 

Legacy Day 2018 honored the Black and White students who participated in the tumultuous early years of integration in Kent County schools. Gradual integration between 1963 and 1967 was the work of more than 100 “pioneers,” Black students who volunteered, or were volunteered by their parents, to attend formerly all-White schools before full integration in 1967. These pioneers included Robert “Bobby” Brown, Michelle Towson, Herbert Warren, Vanessa Isaacs Ringgold, and Ellsworth Tolliver, whose experiences ranged from the good to the bad to the downright ugly.

 

Legacy Day 2019 honored African American churches of Kent County by documenting the history of the 24 early churches, all of which were founded at least 125 years ago and belonged to a branch of the Methodist church. Given the widespread poverty and discrimination that African Americans had to contend with, the construction and preservation of 24 churches (roughly one for every 275 Black residents) represent a remarkable testament to the faith and resourcefulness of their congregations. This achievement also emphasizes the essential role of the Black church as a community institution that not only fulfills spiritual needs but also helps to advance the social, educational, and political aspirations of its members.

 

In response to the covid-19 pandemic, Legacy Day 2020 went virtual with several online events, including a genealogy workshop hosted by the National Museum of African American History and Culture, a spirited discussion of Black student life at Washington College, and a video previewing our tribute to outstanding African American athletes and coaches postponed until 2021.

 

Legacy Day 2021 featured some of the most successful basketball and football teams at Garnet and Kent County high schools, the community baseball teams that flourished in small towns from the 1920s to the 1970s, and the church league basketball teams of the 1970s and 1980s. We honored 44 athletes and four coaches.

 

Legacy Day 2022 saluted more than 1,700 African American men and women from Kent County who served in the United States Army, Navy, Air Force, Marines, and Coast Guard. This record of service began during the American Revolution and continues to the present. During the Civil War, more than 44% of eligible Black men in Kent County, free and enslaved, fought to emancipate themselves, their families, and their brethren, and to preserve the Union. Local African Americans enlisted in significant numbers to fight in every major war of the 20th century. Legacy Day 2022 was a modest effort to say, “Thank you for your service.” 

 

Legacy Day 2023 plans to honor the dozens of volunteers and donors who have produced an annual festival that documents and celebrates aspects of the history and culture of African Americans in Kent County. The Honorees’ Reception will include a special tribute to Airlee Ringgold Johnson, who has provided the indispensable leadership, inspiration, community links, and driving force that have made Legacy Day a success. Visit the Sumner Hall website for a schedule of the free events August 18-20.

 

 

Bill Leary, a retired historian and archivist, is on the board of directors of Sumner Hall. He has worked on Legacy Day exhibits since 2014, shortly after retiring to Chestertown.

 

Common Sense for the Eastern Shore

By CSES Staff October 24, 2025
 Sparking alarm among housing advocates, social workers, and residents, Salisbury Mayor Randy Taylor has announced plans to gut Salisbury’s nationally recognized Housing First program, signaling a break from years of bipartisan progress on homelessness. Created in 2017 under then-Mayor Jacob Day, the initiative was designed around a simple but powerful principle: that stable, permanent housing must come first before residents can address problems with employment, health, or recovery. The program was designed to provide supportive housing for Salisbury’s most vulnerable residents — a model backed by decades of national data showing it reduces homelessness, saves taxpayer dollars, and lowers strain on emergency services. But under Taylor’s leadership, that vision appears to be ending. In a letter to residents, the City of Salisbury announced that the Housing First program will be shut down in 2027, in effect dismantling one of the city’s long-term programs to prevent homelessness. Taylor says he plans to “rebrand” the program as a temporary “gateway to supportive housing,” shifting focus away from permanent stability and toward short-term turnover. “We’re trying to help more people with the same amount of dollars,” Taylor said. Critics call that reasoning deeply flawed, and dangerous. Former Mayor Jacob Day, who helped launch the initiative, says that Housing First was always intended to be permanent supportive housing, not a revolving door. National studies show that when cities replace permanent housing programs with short-term placements, people end up right back on the streets, and that costs taxpayers more in emergency medical care, policing, and crisis intervention. Local advocates warn that Taylor’s move will undo years of progress. “This isn’t just a policy shift, it’s a step backward,” one social service worker said. “Housing First works because it’s humane and cost-effective. This administration is turning it into a revolving door to nowhere.” Even some community partners who agree the program needs better oversight say that Taylor is missing the point. Anthony Dickerson, Executive Director of Salisbury’s Christian Shelter, said the city should be reforming and strengthening its approach, not abandoning its foundation. Under Taylor’s proposal, participants could be limited to one or two years in housing before being pushed out, whether or not they’re ready. Advocates fear this change could push vulnerable residents back into instability, undoing the progress the city was once praised for. While Taylor touts his plan as a way to “help more people,” critics say it reflects a troubling pattern in his administration: cutting programs that work. For years, Salisbury’s Housing First initiative has symbolized compassion and evidence-based leadership and has stood as a rare example of a small city tackling homelessness with dignity and results. Now, as Taylor moves to end it, residents and advocates are asking a simple question: Why would a mayor tear down one of Salisbury’s most successful programs for helping people rebuild their lives?
By John Christie October 24, 2025
On the first Monday of October, the Supreme Court began a new term, Term 2025 as it is officially called. The day also marked John Roberts’ 20 years as Chief Justice of what history will clearly record as the Roberts Court. Twenty years is a long time but at this point, Roberts is only the fourth longest serving Chief Justice in our history. John Marshall, the fourth and longest, served for 34 years, 152 days (1801–35). Roger Brooke Taney, served for 28 years, 198 days (1836–64). Melville Fuller, served 21 years, 269 days (1888 to 1910). John Roberts was originally nominated by George W. Bush to fill the seat held by the retiring Sandra Day O’Connor but, upon the unexpected death of William Rehnquist, Bush instead nominated Roberts to serve as Chief Justice. His nomination was greeted by enthusiasm and high hopes in many quarters. He was young, articulate, personable, and highly qualified, having had an impressive academic record, experience in the Reagan administration and the private bar, and service on the federal D.C. Court of Appeals for two years. His “balls and strikes” comment at his confirmation hearing struck many as suggesting judicial independence. He sounded as well very much like an institutionalist, having said at an early interview that “it would be good to have a commitment on the part of the Court to act as a Court.” Whatever else might be said 20 years later about the tenure of John Roberts as Chief Judge, the Supreme Court is no doubt much less popular and much more divisive today than it was on September 29, 2005, when he was sworn in as the 17th Chief Justice by Justice John Paul Stevens, then the Court’s most senior associate justice, and witnessed by his sponsor, George W. Bush. Gallup’s polling data shows popular support for the Court now at the lowest levels since they started measuring it. In July 2025, a Gallup poll found that, for the first time in the past quarter-century, fewer than 40% of Americans approved of the Supreme Court’s performance. According to Gallup, one major reason that approval of the Supreme Court has been lower is that its ratings have become increasingly split along party lines — the current 65-point gap in Republican (79%) and Democratic (14%) approval of the court is the largest ever. The legal scholar Rogers Smith wrote in The Annals of the American Academy of Political and Social Science in June, “Roberts’s tenure as Chief Justice has led to the opposite of what he has said he seeks to achieve. The American public now respects the Court less than ever and sees it as more political than ever.” These results signify more than simply a popularity poll because a Court without broad public support is a Court that will not have the same public respect upon which their most important decisions have historically depended. And, whatever the reasons for this development, it has happened on John Roberts’s watch. There is no better example of the current divisiveness on the Court than the remarkable string of “emergency” rulings on the Court’s so-called shadow docket since January 20. The extent of ideological and partisan differences has been sharp and extreme. The conservative majority’s votes have frequently been unexplained, leaving lower court judges to have to puzzle the decision’s meaning and leaving the public to suspect partisan influences. And the results of these shadow docket rulings have had enormous, sometimes catastrophic, consequences: Removing noncitizens to countries to which they had no ties or faced inhumane conditions Disqualifying transgender service members Firing probationary federal workers and independent agency heads Ending entire governmental departments and agencies without congressional approval Allowing the impounding of foreign aid funds appropriated by Congress Releasing reams of personal data to the Department of Government Efficiency Allowing immigration raids in California based on racial and ethnic profiling John Roberts has written many Supreme Court opinions in his 20 years as Chief Justice. At the 20-year mark, the most important, to the nation and to his legacy, will likely be his opinion in the Trump immunity case, which changed the balance of power among the branches of government, tipping heavily in the direction of presidential power. Trump v. United States (2024). In her dissent from his majority opinion in that case, Justice Sonia Sotomayor, joined by Justices Elena Kagan and Ketanji Brown Jackson, warned about the consequences of such a broad expansion of presidential power. “The Court effectively creates a law-free zone around the president,” upsetting the status quo that had existed since the nation’s founding and giving blanket permission for wrongdoing. “Let the president violate the law, let him exploit the trappings of his office for personal gain, let him use his official power for evil ends. In every use of official power, the president is now a king above the law.” Roberts claimed in his majority opinion that the “tone of chilling doom” in Sotomayor’s dissent was “wholly disproportionate” to what the ruling meant. However, Sotomayor’s words have proved prescient: the breadth of power that Trump and his administration have asserted in the months since he was sworn in for his second term has made plain how boundlessly they now interpret the reach of the presidency in the wake of the Roberts opinion. Despite the early “balls and strikes” comment, the assessment of John Roberts’ long term judicial record suggests something different as seen by several distinguished legal commentators from significantly different perspectives. As summarized by Lincoln Caplan, a senior research scholar at Yale Law School, in a new retrospective article on Robert’s 20-year tenure, “From his arrival on the Court until now, his leadership, votes, and opinions have mainly helped move the law and the nation far to the right. An analysis prepared by the political scientists Lee Epstein, Andrew Martin, and Kevin Quinn found that in major cases, the Roberts Court’s record is the most conservative of any Supreme Court in roughly a century.” “What Trump Means for John Roberts's Legacy,” Harvard Magazine , October 8, 2025. Steve Vladeck, Georgetown Law Center professor and a regularly incisive Court commentator, characterized the 20-year Roberts’ Court as follows: “The ensuing 20 years has featured a Court deciding quite a lot more than necessary — inserting itself into hot-button social issues earlier than necessary (if it was necessary at all); moving an array of previously settled statutory and constitutional understandings sharply to the right; and, over the past decade especially, running roughshod over all kinds of procedural norms that previously served to moderate many of the justices’ more extreme impulses.” “The Roberts Court Turns Twenty,” One First , September 29, 2025. In another remarkable new article by a widely respected conservative originalist, similar concerns about the present Court have very recently been expressed. Caleb Nelson, who teaches at the University of Virginia and is a former law clerk to Justice Clarence Thomas, has written that the text of the Constitution and the historical evidence surrounding it in fact grant Congress broad authority to shape the executive branch, including by putting limits on the president’s power to fire people. “Must Administrative Officers Serve at the President’s Pleasure?” Democracy Project, NYU LAW , September 29, 2025. When the First Congress confronted similar ambiguities in the meaning of the Constitution, asserts Nelson, “more than one member warned against interpreting the Constitution in the expectation that all presidents would have the sterling character of George Washington.” Nelson continues, “The current Supreme Court may likewise see itself as interpreting the Constitution for the ages, and perhaps some of the Justices take comfort in the idea that future presidents will not all have the character of Donald Trump. But the future is not guaranteed; a president bent on vengeful, destructive, and lawless behavior can do lasting damage to our norms and institutions.” John Christie was for many years a senior partner in a large Washington, D.C. law firm. He specialized in anti-trust litigation and developed a keen interest in the U.S. Supreme Court about which he lectures and writes. 
By Jan Plotczyk October 24, 2025
If you’ve ever wondered just how slavishly loyal Rep. Andrew P. Harris (R-MD01) is to President Donald Trump, you can now put a number on it! Just consult the Republican National Platform Ratings. When you do, you will find that Rep. Harris has a very high overall score: 90.38%. He is the most aligned with the Trump/GOP platform among Maryland’s congressional representatives. No surprise there. Among all U.S. senators and representatives (using 2024 votes), Harris is 43rd most aligned. One might expect more from the chair of the right-wing Freedom Caucus. Harris scores at 90.38% aligned overall. His ratings by topic range from 82.98% to 100%. The topics refer to chapters in the platform: Defeat inflation and quickly bring down all prices. Seal the border and stop the migrant invasion. Build the greatest economy in history. Bring back the American Dream and make it affordable again for families, young people, and everyone. Protect American workers and farmers from unfair trade. Protect our Constitution and seniors. Cultivate great K-12 schools leading to great jobs and great lives for young people. Bring common sense to our government and renew the pillars of American civilization. Government of, by, and for the people. Return to peace through strength. Here are all Harris’s scores:
By CSES Staff October 24, 2025
Several thousand people turned out on Oct. 18 in communities across the Eastern Shore to participate in the national “No Kings Day” protests, joining thousands of simultaneous events nationwide opposing the policies of President Trump’s administration. Demonstrations were held in Salisbury, Ocean City, Easton, Cambridge, Chestertown, and Centreville. These gatherings were part of a broader coalition effort that organizers say reflects frustration with the administration’s direction and a demand for renewed accountability and democracy. Participants across the Shore held signs and expressed concerns about immigration enforcement, executive power, and transparency in government. In jurisdictions that lean Republican and supported Trump in 2024, the rallies underscore a growing discrepancy between voting patterns and present activism. For example, in Queen Anne’s County — where the Trump vote was strong — residents joined the demonstration with statements of surprise at the turnout. Despite the scale of national mobilization, local organizers emphasized that the protest is rooted in community values of fairness, participation, and civic voice. One organizer on the Shore described the event as a reminder that “when people choose to show up, they remind their communities what democracy looks like.” Authorities reported no major disruptions during the Shore events, and police in some areas confirmed the rallies proceeded peacefully. For many in the region, the demonstrations mark an opening moment for more active civic engagement on the Shore, one that observers say could reshape local politics in counties historically seen as less partisan.
By CSES Staff October 24, 2025
The Maryland Democratic Party has launched a statewide initiative, Contest Every Seat, that aims to recruit candidates to run for public office across all levels of government ahead of the 2026 elections. Party officials say the goal is to ensure voters in every district across Maryland have a choice on the ballot. The program will include outreach, training sessions, and support for prospective candidates considering campaigns for local, county, and state positions. “The effort is designed to encourage Marylanders who want to make change in their communities to step up and take action,” the party announced. Interested individuals can visit mddems.org/run for information about the application process and training opportunities. The Maryland Democratic Party said similar initiatives in past election cycles helped increase candidate recruitment in local and rural areas, including the Eastern Shore.
By CSES Staff October 24, 2025
With the federal government now shut down for more than three weeks, Maryland is losing hundreds of thousands of dollars in revenue daily, a reflection of the state’s deep economic ties to the federal workforce. According to the Maryland Comptroller, approximately 230,000 Marylanders work directly for the federal government, with an additional 200,000 employed by federal contractors. The state’s economy, long intertwined with the operations of nearby federal agencies, is feeling the strain as paychecks stall and agencies close. Comptroller Brooke Lierman estimates Maryland is losing about $700,000 in state revenue each day — roughly one percent of the state’s average daily revenue of $100 million. “That is a small piece of our overall state budget,” Lierman said, “but as long as all our federal workers are paid what they are owed, that money will get back to us.” Federal employees generally receive back pay after shutdowns end, but recent statements from President Trump suggesting that furloughed workers may not be repaid have created uncertainty. More than 150 members of Congress, including Maryland’s entire Democratic delegation, signed a letter this week urging the Trump administration to guarantee back pay under the 2019 Government Employee Fair Treatment Act, which requires compensation for federal employees affected by a shutdown, and which Trump himself signed into law. Rep. Sarah Elfreth (D-MD03) said Congress is prepared to defend those protections. “Denying that pay would be illegal, and we will use every tool we have — both in Congress and in the courts — to ensure federal employees are made whole,” she said. During the 35-day federal shutdown in 2019, Maryland lost more than $13 million daily in economic activity and over $550,000 daily in tax revenue, according to state data. This latest shutdown comes amid broader federal workforce reductions under the U.S. Department of Government Efficiency, which announced layoffs earlier this year. A federal judge temporarily halted further cuts on Oct. 15 following a legal challenge. The effects extend beyond government offices. Universities such as Johns Hopkins and the University of Maryland Baltimore Washington Medical Center report disruptions to federally funded research projects and grant cycles. Gov. Wes Moore has directed state agencies to provide emergency support to furloughed federal workers, including housing and utility assistance. On Oct. 17, Moore announced the Maryland Transit Administration will offer free MARC and commuter bus rides to federal employees who show valid government ID. “This is what Maryland does in times of crisis, we band together and help each other out,” Moore said. “But no state can fill the gap created by the federal government. The longer this shutdown lasts, the more pain we will feel.” There is no indication of when negotiations in Washington to end the shutdown will resume.
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