In 1920, Lucchese was arrested in Riverhead, Long Island, on auto theft charges. During his booking, a police officer compared Lucchese's deformed hand with that of Mordecai "Three Finger" Brown, a popular Major League Baseball pitcher. The officer nicknamed Lucchese "Three Finger Brown", an alias that Lucchese always disliked. In January 1921, Lucchese was convicted 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.