Failla was one of the most respected and feared racketeers in New York from from the early 1960s until 1995. Through his control of the Trade Waste Association of Greater New York and Teamsters Union Local 813, Failla was able to squeeze New York businesses out of hundreds of millions of dollars over several decades. He earned the nickname "Jimmy Brown" for his fondness of wearing chocolate brown business suits when out in public. He has a close physical resemblance to American publisher and pornographer Larry Flynt. Failla had a close partnership with the Genovese crime family and it was rumored that the Genovese leadership wanted to install Failla as boss along with fellow captain Daniel "Danny" Marino after a failed assassination attempt on then Gambino boss John Gotti.
Avoiding prosecution for many years, Failla lived modestly and direct a large crew in loansharking, illegal gambling, and extortion. He had a reputation as being one of the most closed-mouthed of all mobsters, as well as one of the all-time top earners in La Cosa Nostra. Although present for hundreds of hours at bugged meetings at Gambino boss Paul Castellano's residence, Failla barely spoke ten words on all the tapes combined. A resident of Ocean Breeze, Staten Island, Failla's nickname "Jimmy Brown" derived from his fondness for brown clothes.
In 1987, Failla was acquitted on federal racketeering charges. In 1989, Failla participated in the murder of Gambino mobster Thomas Spinelli. A member of Failla's crew, Spinelli had recently appeared before a grand jury. Sammy Gravano ordered Spinelli's murder to prevent any further testimony. In December 1990, when Gotti went to jail awaiting trial, he allegedly appointed Failla as acting boss of the family. After Gotti's conviction, Failla served on a three-man panel that ran the family.
In 1994, Failla pleaded guilty to conspiracy to commit murder in the Spinnelli death and was sentenced to seven years in prison. In 1999, James Failla died in federal prison.