James (Jimmy) Kaulentis, Chicago Mercantile Exchange guru, was allegedly very close to the infamous (and now late) Spilotoro brothers, Michael and Tony. Through this connection, Kaulentis met Outfit Capo Joe Lombardo, who is now serving a life sentence because of convictions in the landmark federal criminal case dubbed “Family Secrets.” However, one other Outfit bigwig who “inherited” Jimmy Kaulentis is underboss emeritus Joe “The Builder” Andriacchi. Of course, where there is illicit income for Andriacchi, there is a portion for Outfit boss John DiFronzo.
Primarily through Andriacchi, Kaulentis allegedly funded Outfit bookmaking operations beginning approximately in the late 1990s, by initially giving then Outfit Lieutenant Michael Magnafichi a generous six-figure loan that would not have to be repaid. It is heavily rumored that Kaulentis allegedly financed a number of Andriacchi’s land development projects as well.
When I learned about Kaulentis’ alleged generosity with gangsters, I wondered how one could be willing to use his or her money in such a wasteful and shameful way. However, after I learned more about Kaulentis I realized the answer. According to reliable sources, Kaulentis allegedly targeted several young traders at the Chicago Mercantile Exchange over about a 10-year period. Allegedly, Kaulentis would make contact with his intended victims through trusted co-conspirators, claiming to be in a position of power, capable of buying off potential witnesses who would otherwise cooperate with federal authorities in bringing charges of insider trading infractions against the intended target. It would be the victim’s money that Kaulentis would allegedly use to pay off the supposed witnesses. There is no telling how much illicit cash Kaulentis could have brought in for the Chicago Outfit via his alleged scheme.