McDaniels' graduation date will come 50 years and a month after Marshall, then the chief counsel for the NAACP, won his historic fight to desegregate Douglass and every other public school in America. Marshall argued that integrated schools would offer more academic opportunities for blacks and more social possibilities for both blacks and whites.
But a half-century later, Douglass is just two white students shy of being as segregated as it was when Marshall walked the halls of the original school, which closed in 1954 when the students moved to the current site on Gwynns Falls Parkway.
Instead of improving after Brown vs. Board of Education, the U.S. Supreme Court ruling that outlawed segregation, Douglass got worse. But over the past 10 years, the West Baltimore school has slowly begun to better itself, thanks largely to a state intervention tool called reconstitution, and new school leadership.
Dropout rates have fallen to single digits. The graduation rate doubled last year to 56.6 percent, the highest in many years.
Charles McDaniels, who lost both of his parents when he was 8 years old, will graduate from Douglass with honors and go on to Coppin State University in the fall.
"There are a lot of teachers [at Douglass] who really care about the futures of the students that they have in their hands," the 17-year-old said. "And they really strive to give the best education possible."
Blow to tradition
Still, today's Douglass High scarcely resembles the proud place that older alumni fondly remember.
Test scores are low. The building needs repairs. Alumni complain that many of today's students seem not to recognize the community jewel Douglass was. Or worse, they don't care.
"The school was so classy, we called it 'the public private school,'" said Rose Hillery Jones, who graduated from segregated Douglass in 1947. "Today, children are profane. When I have occasion to drive by there, all of the worst language that you can hear comes out of their mouths."
Five decades after Brown, many pre-Brown alumni say desegregation was a blow to the tradition of excellence at Douglass - the school that issued diplomas to many of the city's most famous black citizens, including Marshall, NAACP leader Kweisi Mfume, jazz great Cab Calloway, former Rep. Parren J. Mitchell and Clarence H. Du Burns, the city's first black mayor.
"Desegregation destroyed us," said the Rev. Vernon Dobson, a 1941 Douglass graduate and pastor of Union Baptist Church in West Baltimore, which has a century-old tradition of civil rights activism.
Integration skimmed off the school's best students and staff and many of those left behind were trapped in poverty.
"We sent our best and brightest to [Baltimore Polytechnic Institute], and City and Western. We sent them to say, 'Blacks can learn just as well as the others,'" said Richard Holley, class of 1953 and chairman of the Douglass High School Alumni Association. "And we sent our teachers right along with them. We replaced [racial] segregation with intellectual segregation. And so we have this two-tracked system now."
During a recent discussion in Sharon Blake's American Government class, a group of sophomores, juniors and seniors debated the merits of the Brown decision, and could come to no clear conclusion.
"Why do some people say that nothing's changed?" asked sophomore Alex Stackhouse, 16. "I see change. The white government allows us to shop in the same stores, walk the same streets and sit in class together."
"But then, you can look around in this classroom and see all black people," argued senior Derrian Smith, 17.
"That's 'cause white people don't want to sit in here with us," complained junior Brandon Gillis, 16.
Even Blake, a city schoolteacher for 30 years, laments the dearth of resources for her students - many who come to her already far behind. She would have liked, she said, to have downloaded audio versions of Thurgood Marshall's desegregation speeches during this lesson, and have her government students hear the force in his words, the conviction in his voice. But her classroom, like most at Douglass High, lacks Internet access - something Blake says is probably a staple at schools in Baltimore's wealthier, whiter counties.
Older alumni remember living in Leave it to Beaver-like neighborhoods, with two parents at home, daily chores done happily, nightly family dinners, flower boxes, scrubbed porch steps and widespread respect.
"Many of the students at Douglass came from families that were considered the upper echelon of Baltimore City," said city school board member Camay Murphy, the daughter of Cab Calloway. "Many of the children were children of professional people. There were very high standards that were kept and maintained."
Even a few years after desegregation, Douglass continued to thrive, alumni remember, though the success would prove fleeting.
"We were not a ghetto," said Douglass Principal Isabelle Grant, who graduated in 1963 from the school she now leads. "We considered ourselves as poor people, not ghetto people."
In Douglass' neighborhood, middle-class blacks moved out and drugs moved in. The family structure crumbled as the welfare system grew, and fewer fathers were in the home.
According to the 2000 Census, households in the communities surrounding Douglass High are overwhelmingly poor - bringing in close to $10,000 less on average than those in the rest of the city. Also, nearly 60 percent of those households are headed by women.
There are more people in the school's surrounding neighborhoods who aren't working than are. And according to the Maryland Alcohol and Drug Abuse Administration, Douglass High sits in a zip code that "shows a higher need in the areas of HIV cases, arrests, and admissions [to drug and alcohol treatment centers]."
Directly across the street from Douglass, the Mondawmin Mall shopping center has sneaker shops, jewelry stores, hair salons and fast food. It also houses a parole office, two rehab centers and a WIC office.
"Living in the inner city, like the neighborhoods that's around this school, it's a lot of drug traffic, and parents that's on drugs," said Douglass senior and peer mediator Carolynn Washington, 18. "And you carry that baggage with you to school every day."
Even some of Douglass' high achievers are no strangers to societal baggage.
Take Shoska Manson, this year's class valedictorian, who has been raised by a friend of her adoptive mother's, because her adoptive mother died of AIDS when Shoska was small.
Shoska, 17, has found her birth mother but hasn't been able to bond with her.
"I've tried, but I don't think she wants to," said Shoska of her efforts to reach out to her mother, adding, "I've never really had a home home. So school is something that I had to do for myself."
The father of her friend Charles McDaniels died of liver disease days before Charles' 10th birthday. A week later, Charles' mother died of breast and bone cancer.
"You don't get over it," said McDaniels, who lives with an aunt in Bolton Hill. "You deal with it. It's something that motivates you to keep on going. When I wake up in the morning and look in the mirror, I say to myself, 'I can't let everybody down.'"
That kind of self-determination is reminiscent of the pre-integration Douglass - the "glory days," as alumni call them - and offers a glimpse of hope for Douglass' future.
" ... Our aim was always to be better. In the whole world, we had to be better," said Barbara Shaffey Leak, of the class of 1943. "Our motto was 'Pride, Dignity and Excellence.' And we believed that with every fiber of our being. And we acted it out every day."
Desegregation might have taken a toll on that kind of drive. But many Douglass alumni say they believe Thurgood Marshall's intentions have proved fruitful.
"The finest education I ever received was at Douglass High School," said Sydney Cousin, superintendent of schools in Howard County. "And other people will tell you this same thing."
But he credits his success to his teachers at Douglass and the high standards he was required to meet. Miss Buchanan, Cousin's Latin teacher, even gave homework over the summer, he remembers; Cousin still can recite the Pledge of Allegiance in flawless Latin.
"At the time you thought they were the strictest teachers in the world, but I learned to read with comprehension sophisticated literature, and how to write effectively, and to appreciate books and writings of all types," Cousin said.
The vestiges of de jure segregation lingered even after Thurgood Marshall's 1954 victory, forcing Cousin and his classmates to continuously count their post-Brown blessings.
"In Mr. Payne's chemistry classroom - I remember it like it was yesterday - I was in the 11th grade and we got new chemistry textbooks," Cousin said. "It was such a big deal. In all our old books, you could see over the years where the books came from. It was always some white school. Mr. Payne was so excited about it, it almost brought tears to his eyes. It made us afraid to use the textbooks."
Disagreeing with many older alumni, some experts say the worn and dated textbooks, poorly trained teachers and inadequate facilities that were indicative of a segregated school system did more to harm black students than the dissolution caused by court-ordered integration.
Just days away from becoming what he hopes is another on the long list of successful Douglass alumni, Charles McDaniels said he is grateful for what Thurgood Marshall accomplished.
"Being desegregated gives people a chance," Charles said. "And I think, with students like us, you're going to see that [pre-Brown pride and excellence] again. Sometimes it takes the next generation to see what the previous generation missed. We can see where they were and where we want to go."