[14] In the 1960s, among students citywide, truancy increased and socializing gained priority, whereby other high schools often issued diplomas once their requirements were met via Roosevelt's evening and summer classes.

[14] Although heroin lowered gang violence,[14] New York City teetered on bankruptcy in 1975,[19] and the 1977 blackout incited massive looting, triggering a domino effect of rapid urban decay,[20] including soaring crime rates and white flight.

[40] Throughout the 1920s, upscale apartments, highly coveted, rapidly went up along the Grand Concourse, and were promptly rented mostly by affluent doctors, lawyers, and businessmen.

[42][43] By 1922, Theodore Roosevelt High School had over 1460 commercial students,[38] who were focusing on accounting or secretarial skills in programs ranging from one to four years.

[44] And yet the borough's Democratic Party's boss, Edward J Flynn, had close ties with Franklin D Roosevelt—previously New York state's governor and a cousin of Theodore Roosevelt—who became US president in 1933.

[44][45] Reachable locally by trolleys,[42] Orchard Beach, unlike the carnival atmosphere in Brooklyn at Coney Island, had elegant bathhouses, and was called by a community leader "The Riviera of the Bronx".

[46] Covering two city blocks square, Theodore Roosevelt High School's building was among America's largest and best equipped with science laboratories, sewing and music rooms, automotive and woodworking shops.

[47][48] The Bronx was home, then, mostly to American whites, whereas Irish were the predominant minority group, while both Italians and Jews were increasing, and blacks were scarce.

[49] Having fled famine in the 19th century and commonly worked in America laying railroads,[41] the Irish, the earliest immigrants, dominating the area, frequently harassed Jews,[49] whose families, however, were usually fervent about education.

[41][52] In 1930, holding a master's degree in education from Columbia University, Sarah L Delany, stymied in securing a job in her area of expertise, at last maneuvered to be hired before the school's administration had met her.

[12][53] On her first day of work, Delany was a shocking sight and awkward presence—a black woman teaching at a "white high school"—but, already hired through bureaucratic formality, was too difficulty to release.

[14] Focused on adolescence as a period to integrate youth, especially from immigrant populations, into society via high school,[36] American educators emphasized voluntary participation in extracurricular activities.

[56] In 1938, while still a Theodore Roosevelt High School student, June Allyson joined the Broadway chorus line Sing Out the News.

[2] On October 8, 1940, vowing to keep America out the war, Wendell Willkie, the Republican Party's presidential candidate for that year's election, gave a speech at Theodore Roosevelt High School,[10] and died that day in 1944.

[60] For many adults, including some who taught at Roosevelt, the 1945 death of President FDR—in the White House a dozen years while leading America through the Great Depression and World War II—severed a sense of continuity with the past.

[61] In 1947, opposing communism, the Catholic War Veterans of New York accused the city's Board of Education of aiding subversives by letting the communist group American Youth for Democracy hold meetings in Roosevelt's building, which was similarly used by diverse organizations.

[63] A Sporting News article of June 10, 1959, named him the American League player most likely to break Babe Ruth's record, 60 home runs in a season.

[64] Roosevelt students of the late 1960s included Ace Frehley, later the lead guitarist of Kiss, and Chazz Palminteri,[32] later the actor whose 1988 play A Bronx Tale was partly his own childhood memoir, based in Belmont.

[66] Palminteri, too, had attended Clinton, but, disliking its being all male, transferred to Roosevelt, where this poor student, who got girls to do his homework, graduated in 1973 at age 21.

[67] Although later actor Jimmie Walker's diploma was from Clinton, he met its requirements in 1965 by attending night classes at Roosevelt,[15] whose summer sessions, too, taught students of other high schools.

[68] After similar moves to New York, emigrant blacks from the American South and from the Caribbean increasingly emerged from poverty, a progress that slowed in the 1960s and halted by about 1970, however, amid rising stagflation and US government's focus on the Vietnam War.

[23] Many Bronx neighborhoods, resembling rubble by 1979, went aflame, while apartment buildings were abandoned or else sold to lesser landlords amid severe, rapid urban decay.

[70] From 1970 to 1980, New York City's population fell from nearly eight to a little over seven million via white flight, while crime, ranging from vandalism to murder, soared, and then, nearly midway through the 1980s, the crack epidemic struck[18][22] Bronx high schools were reputed as the city's worst,[25] while Theodore Roosevelt High School signified the degeneration.

[28] In 1989, a pilot program at Evander Childs High School found metal detectors at student entrances effective, especially as to guns.

[87] In September 1997, Baxter had begun "moral and efficacy" seminars where freshmen were shown videos and discussed issues of school attendance and right versus wrong.

[82] Roosevelt also began a "Saturday Institute" where some 500 middle-school students and their parents attended workshops and tutoring to help prepare for high school.

In 1998, the same English teacher, Frank Brown, simultaneously the soccer coach, led the Roosevelt team against Martin Luther King High School in the championship game.

[90] During it, Roosevelt learned and immediately alerted the governing bureau that two of King's star players were ineligible, having played in Nigeria too many high-school seasons.

[94] Finding "crossover value" in SEAL activities, Baxter commented, "To prepare to be academically successful, kids need to develop their bodies and minds".

[98] In the summer of 1999, Chancellor Crew approved the appointment of Roosevelt's principal Thelma Baxter to a new position, the superintendent of School District 5,[99] located in central Harlem.