He was married to an Italian-American housewife and drove a burgundy 1962 Ford Thunderbird on a desolate street at night in his home city of Newton. He left behind a wife and no children. In 1966 Stephen Flemmi, acting as an informant told FBI agent H. Paul Rico that Rocco was robbing illegal card and dice games. There had been two dice games and three high-stakes card games that were held up by DiSiglio within three weeks. The most recent brazen robbery was on April 9, 1966 when five men burst in on a dice game that was happening at an address on the corner of Morton and Blue Hill Avenue in Mattapan, Boston with Bernard Zinna and Richard DiVincent, armed with sawed-off shotguns. They were robbing lucrative card games that he controlled in his territory of Newton and Lowell, Massachusetts overseen by Gennaro Anguilo, gambling czar for the Patriarca crime family which at the time was headed by Raymond Patriarca. They robbed the players of an estimated $4,500. None of the individuals bothered to wear ski masks during and all appeared to be of Italian ethnic extraction. DiSiglio was the "inside man" who saw to it that the door was unlocked for Zinna and DeVincent to come in unannounced and surprise the card players. One of them made a comment to the card players, "Larry told you not to run." Flemmi advised the Federal Bureau of Investigation (FBI) that this was a reference to Ilario Zannino who oversaw a lucrative illegal barboot game that ran on Sundays in the neighborhood. One of the card players at this game had been relieved of $10,000 and he had just borrowed the money from a Jewish loan shark named "Richfield" in the North End, Boston so he could act as a loan shark at the high-stakes card game for unfortunate players. Patriarca crime family underboss and acting boss Gennaro Anguilo of the Angiulo Brothers quickly became infuriated with DiSiglio's maverick actions and robbing the patrons of his gambling operations. In 1968, Patriarca crime family capo Gennaro Anguilo and two others were arrested and charged with first degree homicide but later acquitted. In August 1967, after H. Paul Rico testified before a Suffolk county grand jury about his conversations with Joseph Barboza concerning the murder of DiSiglio, the Boston SAC sent an urgent teletype to J. Edgar Hoover at 1:03 a.m.