With the leadership of the Detroit Outfit over or fast approaching the age of 70, Jackie "the Kid" Giacalone has emerged as the the heir apparent to the kingdom that is now run by Giacomo Tocco. The kid is the nephew of Anthony Giacalone and the son of Vito Giacalone. Jackie's rise in the Detroit Outfit has been duly noted by various law enforcement agencies, yet he remains an almost invisible underworld figure. Ignored by the media and unrecognized by casual mob watchers, the first sign of his stature within the Outfit occured when Jackie established Farm Fresh Produce Wholesalers in March of 1982. Farm Fresh moved into a building located at the corner of Adelaide and Riopelle streets in Eastern Market. The office actually served as the meeting place for members of the Giacalone Group Enterprise "headed up by Billy Jack, uncle Tony, Jackie and Anthony Giacalone, Jr., "the son of Tony Jack," and their associates to discuss gambling related activities".
The Farm Fresh office became the site of one of the most aggressive wiretapping operations pulled off by the FBI up to that time. Federal agents began investigating the activities conducted at the office shortly after receiving a tip from two unidentified sources that gambling activities were being discussed within the confines of the seemingly legitimate business. Agents not only applied for a warrant to enter the premises and plant a bug but also took the extraordinary step of bugging the entire block of Riopelle and Adelaide streets in an effort to collect incriminating conversations that may have taken place during walk talks held by Vito Giacalone and his minions. The operation which lasted from August to December of 1982 resulted in the indictment of Vito, Jackie, Anthony Giacalone, Michael Santo Polizzi and 9 others on charges of running Operating an illegal gambling business and violation of RICO statutes.
Jackie settled his legal problems with a guilty plea in exchange for a 2 year prison sentence. Giacalone who began serving his sentence on October 2, 1987 was seemingly a minor player in the whole scheme but his true position would later be revealed upon his return to gambling activities as an active and vocal leader in the crew headed up by his father and uncle. Following his release from prison late in 1989, Jackie began expanding his influence and reputation not only among the Partners but nationally as well. The Kid would join with legendary Detroit bookmaker Henry Allen Hilf in establishing a nationwide bookmaking operation that operated in Michigan, Miami, Pittsburgh, New York, Las Vegas and the Ohio Valley. The ring which reportedly made as much as $250,000 a week was broken up in 1991 and Jackie once again pled guilty and received 30 months in prison for his role. Jackie once again emerged from prison and continued his involvement in syndicate activities this time providing himself with a layer of insulation by using long time family friend Frank Bommarito to pass on his requests and orders.
Jackie was named in testimony given by John Pree "a turncoat associate of the Giacalone Group Enterprise," in connection with a string of firebombings, beatings and extortion attempts which according to Pree were all committed on the orders of Jackie the kid. Pree also accused Giacalone of arranging the theft of a shipment of Christmas trees and a skip loader which would be sold and the proceeds split among the perpetrators of the crimes. With the information provided by John Pree, prosecutors and FBI agents began looking at a possible RICO case against the kid but Jackie managed to escape unscathed when John Pree suddenly quit talking and asked that his plea agreement with authorities be cancelled even though he would have to serve a total of 27 years in prison before he would be allowed to apply for parole. As a result Jackie the kid continues his climb through the ranks of the Partnership now operating in the role of boss of the Detroit gambling fraternity while ranking as a lieutenant for Jack Tocco and the Detroit Partnership.
Upon longtime boss Giacomo Tocco's death in 2014, Giacalone rose to the position of boss.