After his accident, Lucchese spent more time with members of the 107th Street gang. Members of the gang stole wallets, burglarized stores, and engaged in other illegal activities. The 107th Street gang operated under the protection of Bronx–East Harlem family boss
Gaetano "Tom" Reina. By the age of eighteen, Lucchese had started a window washing company in East Harlem; anyone refusing to use his window washing services would have their windows broken. The officer nicknamed Lucchese "Three Finger Brown", an alias that Lucchese always disliked. of auto theft and sentenced on March 27, 1922 to three years and nine months in prison. Lucchese served thirteen months at
Sing Sing Correctional Facility before he was paroled. It would be Lucchese's only conviction. Lucchese was released from prison in 1923, three years into
prohibition. His old friends Charlie Luciano,
Frank Costello, and
Meyer Lansky had become partners with Jewish gangster
Arnold "the Brain" Rothstein selling
bootleg alcohol. In August 1927, Lucchese was arrested under the alias of "Thomas Arra" and charged with receiving stolen goods. On July 18, 1928, Lucchese was arrested along with his brother-in-law, Joseph "Joe Palisades" Rosato, for the murder of Louis Cerasuolo; the charges were later dropped. Lucchese was arrested on three other occasions in his lifetime: in 1930 for murder, in 1931 as part of an investigation, and in 1935 for vagrancy, but in all three cases he was released and all charges were dropped. ==Castellammarese War==