According to one historian, "it would be a mistake to identify the Bowery Boys as a specific group at a specific time . . .there were several gangs who referred to themselves as the Bowery Boys at various times under different leaders during the antebellum years." Mike Walsh was largely considered the leader of the one of the first incarnations of the Bowery Boys. Walsh acted as a political figure to the Bowery Boys and even became an elected official. He reached the peak of his popularity in 1843, when he created the political clubhouse he called the "Spartan Association", which consisted of factory workers and unskilled laborers. Walsh felt that political leaders were treating the poor unfairly and wanted to make a difference by becoming a leader himself. Walsh was sentenced to jail twice, but the Bowery Boys became so powerful that they were able to bail him out during his second trip to jail. The front page of The Subterranean on April 4th read, "We consider the present infamous persecution of Mike Walsh a blow aimed at the honest laboring portion of this community". Due to the threat of violence in the streets, Walsh was let out midway through his sentence. Walsh was considered by many to be the "champion of the poor man's rights". Walsh was eventually taken to Tammany Hall and was nominated for a seat in the state legislature, and even earned the support of poet Walt Whitman. Walsh eventually died in 1859 and his obituary in an edition of The Subterranean read that the leader of the Bowery Boys was an "original talent, rough, full of passionate impulses... but he lacked balance, caution-the ship often seemed devoid of both ballast and rudder". The obituary was thought to be written by Whitman. During the New York Draft Riots of 1863, the Bowery Boys reached the height of their power taking part in the looting of much of New York City while fighting with rival gangs, the New York Police, and the Union Army. By the end of the decade, however, the gang had split into various factions as the Bowery Boys gradually disappeared.
The Bowery Boys were known to frequent theaters in New York City. Richard Butsch from The Making Of American Audience's said that, "they brought the street into the theater, rather than shaping the theater into an arena of the public sphere". The Bowery Theater, in particular, was a favorite among the Bowery Boys. The Bowery Theatre was built in 1826 and soon became a theater for the working man. Walt Whitman described the theater as "packed from ceiling to pit with its audience, mainly of alert, well-dressed, full-blooded young and middle aged men, the best average of American-born mechanics". Plays even began to appear in theaters frequented by the Bowery Boys with shows about Bowery Boys themselves. Particularly, a character named Moses who many Bowery Boys deemed as "the real thing". It was not uncommon for men to drink, smoke, and meet with prostitutes in the theater. The Bowery Boys dominated the theater in the early 19th century and theater was considered to be a "male club".
The interior of the Bowery Theatre