In the early 1950s, the Nationalist Party began a series of revolutionary actions, including the 1950 Jayuya Uprising against American presence on the island.

As part of this initiative, Pedro Albizu Campos ordered Lebrón to organize attacks in the United States, focusing on locations that were "the most strategic to the enemy."

During the following years, Lebrón continued her involvement in pro-independence activities, including the protesting the existence of a United States Navy base at Vieques.

[6] When Lebrón completed the sixth grade she attended the Segunda Unidad Rural, a middle school located in Bartolo, an adjacent barrio.

[8] Lebrón had uncommonly good looks and when she was a teenager won first place in the annual "Queen of the Flowers of May" beauty contest held in Lares.

However, her posture changed after March 21, 1937, when a group of militants from the Puerto Rican Nationalist Party were killed during a peaceful protest which became known as the Ponce massacre.

When she was twenty-one years old she gave birth to her first daughter Gladys, who was left in Rafaela Luciano's custody after Lebrón was separated from her husband and moved to New York City.

The Senate, controlled by the Partido Popular Democrático (PPD) and presided by Luis Muñoz Marín, approved the bill that day.

[31] Under this new law it would be a crime to print, publish, sell, or exhibit any material intended to paralyze or destroy the insular government; or to organize any society, group or assembly of people with a similar destructive intent.

According to Dr. Leopoldo Figueroa, the only non-PPD member of the Puerto Rico House of Representatives, the law was repressive and was in violation of the First Amendment of the US Constitution which guarantees Freedom of Speech.

Following the sentence, Lebrón quickly joined the "Committee for Oscar Collazo's defense", participating in numerous public manifestations which eventually led to a presidential commutation.

[33] On July 25, 1952, the official name of Puerto Rico was changed to Estado Libre Associado (commonwealth of the United States) as a constitution was promulgated by Luis Muñoz Marín, the islands' first elected governor.

[34] Albizu Campos had been corresponding with 34-year-old Lebrón from prison and chose a group of nationalists who included Rafael Cancel Miranda, Irvin Flores and Andres Figueroa Cordero to attack locations in Washington, D.C.

[34] Lebrón intended to call attention to Puerto Rico's independence cause, particularly among the Latin American countries participating in the conference.

After completing the first 15 years of the sentence, Lebrón's social worker told her that she could ask for parole, but she did not display interest in the proposal, never signing the required documentation.

[50] Due to this lack of interest, she was mandated to attend a meeting before a penitentiary committee, where she presented a written deposition expressing her position about the parole proposal, as well as other subjects including terrorism, politics, and the United States' use of the atomic bomb.

[51] Following this, the other inmates reacted with skepticism over her intentions to refuse the offer, which made her distance herself from them, and focus her attention in studying, as well as writing poetry.

In 1979 President Jimmy Carter commuted the sentences of Lolita Lebrón, Irvin Flores, and Rafael Cancel Miranda after they had served 25 years in prison.

[54] In 1979, Lolita Lebrón, Irvin Flores, Rafael Cancel Miranda and Oscar Collazo were recognized as the embodiment of the directive of their teacher Albizu Campos to exercise valor and sacrifice before representatives of fifty-one countries at the International Conference in Support of Independence for Puerto Rico, held in Mexico City.

[citation needed] On May 22, 2000, she erroneously filed charges of verbal assault against Nívea Hernández, the mother of then-Puerto Rico Senator Kenneth McClintock who subsequently served as Minority Leader, and later President, of the Senate of Puerto Rico and now serves as Secretary of State, after a discussion ensued between her and an unidentified woman at a pharmacy in San Juan.

According to the local newspaper El Vocero, her audience applauded when Lebrón said at the end of her deposition "I had the honor of leading the act against the U.S. Congress on March 1, 1954, when we demanded freedom for Puerto Rico and we told the world that we are an invaded nation, occupied and abused by the United States of America.

[66] Multiple public figures, who support independence or free association for Puerto Rico, immediately lamented Lebrón's death, praising her activism.

Mexican artist Octavio Ocampo created a poster of Lebrón, which was exhibited at the Galería de la Raza in San Francisco, California.

The artist was interested in learning about political prisoners being held in the United States, and Lebrón stood out to her as a potential subject for a poster regarding the formation of a community.

[69] Furthermore, as a resident of San Francisco’s Mission District, a region whose Latino population featured only a small percent of Puerto Ricans, Lucero’s decision to depict Lebrón was unexpected, and perhaps reflected the “internal colony” thesis.

[70] One of the most often discussed elements of the work is that Lebrón, typically regarded as a white woman by Puerto Ricans, is rendered in burnt sienna to highlight her brown skin.

In contrast to Lucero’s suffering Lebrón, or the media’s description of her as a terrorist, with headlines such as “When terror wore lipstick,”[73] Dimas represents a portrayal of Lolita Lebrón that scholars regard as “heroic,” showing her in three-quarter profile with her eyes defiantly raised and staring ahead in determination, repeated four times in the same color palette on the poster, and declaring her as a “Puerto Rican Freedom Fighter”.

The author criticizes her grandmother as a distant, gun-toting, larger-than-life figure who cast a veil of pain and secrecy over her family so vast that Ms. Vilar is still untangling herself from it.

[citation needed] Lebrón's granddaughter, Vilar, may have had a slight change of heart after Hurricane Maria devastated Puerto Rico.

Vilar appealed for donations of seeds (farmers had lost everything), and received "so many we didn't know what to do with them" so she started the "Resilience Fund" with Tara Rodriguez Besosa.