Tonight's I-Team report: why the life of a tough attorney who defended mobsters would end this way.
In the end, Rick Halprin's life was dominated by debts and pain. On Tuesday morning, when Cook County Sheriff's deputies showed up at Halprin's Hyde Park apartment with an eviction notice, both of those got the best of him.
He was found dead with a single gunshot wound to the head. Authorities consider it a suicide.
Rick Halprin had deep roots in Chicago's legal landscape for forty years, since attending John Marshall Law School.
He handled big cases and was always a compelling and strong advocate for clients, whether they were gangsters or gang bangers.
In federal court, Mr. Halprin was on the short list of go-to attorneys for criminal customers facing deep trouble.
"He was very caring about his clients, he was very honest with his clients, he would not solemn amazing promises to get into a case," said Joe "the Shark" Lopez, a lawyer and friend of Halprin.
Halprin was a protégé of the famed criminal defense attorney Frank Oliver and always ready with a toasty quip for the cameras.
Halprin's close friend Tom Durkin tonight says he was one of the best lawyers he ever met, but that the ex-marine lived in constant pain from a serious wound during the Vietnam War that left him with metal rods in his back.
Recently his pain had become unmanageable.
It was against that backdrop Tuesday morning that sheriff's deputies came to his sixth floor apartment with an eviction notice, and an undercurrent of financial ruin.
He had a half million dollars in federal and state tax liens the past few years, with a $200,000 IRS lien coming just last December.
"He would live the day to its fullest every single day. He was kind of the guy, you know, 'to hell with tomorrow, live for today' kind of guy," said Lopez.
According to friends, Mr. Halprin had significant debts following several divorces, had recently stopped practicing law and gave up his license, and was told by doctors that his back injuries could no longer be safely treated.
Tuesday morning was the bottoming out for a man who spent many years at the top of his game.