When he was six years old, Rodwell's mother, Marion Kastman, fearing that the child care set up could cause her to lose custody of her son, arranged for his admission to the Christian Scientist affiliated Chicago Junior School (later called the Fox River Country Day School[7]) for "problem" boys, in Elgin, Illinois.

He later said, “This is what I lived for, literally.” When Rodwell was 14, he was charged and convicted by the Chicago police for juvenile delinquency when he was caught walking home after having sex with a man in his thirties.

[13] In 1962, Rodwell had a romantic relationship with Harvey Milk, who went on later to become one of the first openly gay politicians elected to high office.

After Rodwell's arrest and incarceration when picked up cruising in Washington Square Park, Milk ended their romantic involvement.

[4] Rodwell conceived of the first yearly gay rights protest, the Annual Reminder picketing of Independence Hall held from 1965 to 1969;[20] Homophile Youth Movement rallies in 1967, and was present at the Stonewall Riots in 1969.

[26] On April 18, 1965, Rodwell led picketing at the United Nations Plaza in New York to protest Cuban detention and placement into workcamps of gays, along with Wicker, Allen Ginsberg, Peter Orlovsky and about 25 others.

[28][29] On April 21, 1966, Rodwell, along with Mattachine President Dick Leitsch and John Timmons engaged in a demonstration then called a "Sip-In" at Julius, a bar in Greenwich Village, to protest the New York State Liquor Authority rule against the congregation of gays in establishments that served alcohol.

As the police began to bring arrestees from the bar to a paddy wagon, Rodwell led a chant, "Gay Power!"

They continued their organizing and leafletting throughout the nights of rioting, distributing 5,000 copies of their "Get the Mafia and Cops Out of Gay Bars" flyer throughout New York City.

[34] In November 1969, Rodwell proposed the first gay pride parade to be held in New York City by way of a resolution at the Eastern Regional Conference of Homophile Organizations meeting in Philadelphia, along with his partner Fred Sargeant (HYMN vice chairman), Ellen Broidy and Linda Rhodes.

[35] That the Annual Reminder, in order to be more relevant, reach a greater number of people, and encompass the ideas and ideals of the larger struggle in which we are engaged-that of our fundamental human rights-be moved both in time and location.

[36][37][38][39]Rodwell is believed to have created the term heterosexism in January 1971 when he wrote: After a few years of this kind of 'liberated' existence such people become oblivious and completely unseeing of straight predjudice [sic?]

[46][47] The SNM is the first U.S. national monument dedicated to LGBTQ rights and history,[48] and the wall's unveiling was timed to take place during the 50th anniversary of the Stonewall riots.