On Thursday, he was handed his punishment.
From the beginning of Family Secrets, Anthony Doyle tried to cultivate sympathy by making himself out as a poor Chicago kid who began his public service career pushing Streets and Sanitation trash carts to help his family and from there worked his way up to a beat cop.
Doyle even changed his last name from the Italian Passafume so he would fit into an historically Irish police force.
But the jury that convicted Doyle never bought his well staged version of the American dream and on Thursday neither did U.S. District Judge James Zagel.
The 64-year-old Doyle had proposed being cut loose on probation but Zagel wouldn't have it.
Before sentencing Doyle to 12 years, Judge Zagel said, "It's a fact of life that you can be a stellar police officer one day and a criminal the next."
"I would have been much happier if Mr. Doyle had been released today, but I'm grateful that Judge Zagel took into consideration that Anthony Doyle was an exemplary police officer," said Ralph Meczyk, Doyle attorney.
Doyle - whose nickname 'Twan' either refers to a slang version of Anthony or a Chinese donut popular in the 26th Street neighborhoods where Doyle ran - is the last of five mob bosses and associates convicted of racketeering in the landmark Family Secrets trial.
In court on Thursday afternoon, assistant U.S. Attorney T. Markus Funk said, "The reality is that this man is a disgrace."
Even while he was a Chicago cop, Doyle made regular visits to a Michigan prison where he fed police information to convicted Outfit hit man Frank Calabrese Sr.
The beefy Doyle moonlighted as an enforcer, mob "street tax" collector and even though he surrounded himself by cold-blooded killers, he was not held legally responsible for any of the 18 mob murders described in the indictment.
Doyle apologized in court on Thursday for his "lapse in judgment" and for the pain he caused his family and friends.
Doyle faired better than his four counterparts who were sentenced to life in prison.
There is still one more Family Secrets mobster to be sentenced, the star witness in the case, Nick Calabrese. He was involved in more killings than any of those charged. But because he opted to work for the government, Nick Calabrese was able to cut a deal with the government and avoid prosecution.