After he finished law school, Halprin landed a job with fellow attorney and neighbor Jerry Feldman. Feldman had a general practice, but Halprin's desire to practice criminal law soon got the best of him—he was ready to swim with the real sharks.
Approximately a year after he graduated from law school, Halprin was given the opportunity to work for now-retired Chicago trial lawyer Frank Oliver. Though Halprin basically started out as Oliver's right-hand man, he was exposed to all the ins and outs of criminal law, and the foundation of his career was built. "I wanted to grow as a criminal defense lawyer, and Frank provided that opportunity for me," said Halprin. Today, Halprin runs his own criminal defense practice, which he started in 1970.
Halprin's criminal-defense mentor, Oliver, represented several mob-related cases during his years as a lawyer, which may have directed Halprin to one of his most famous clients: Lombardo, one of the most notorious mobsters and a high-ranking member of the Chicago Outfit (the city's organized crime family). Halprin has been Lombardo's attorney for approximately six years.
But Lombardo's trouble dates back much further than that. The U.S. government has been on Lombardo's tail for quite some time. Lombardo has been wrapped up in a series of conspiracy cases, some he served time for and some he did not, since at least the 1960s. "In all mob cases, it's guilt by association. It's the whole concept," said Halprin. "All of us know what happens in conspiracy cases; you get swept up in that dragnet. But they're here to stay, so there's no sense talking about it."
Currently, Halprin is representing Lombardo in a case that has been stretching on for more than a month now. Besides the fact that the indictment goes back 43 years, this is not your typical mob case. The case, coined the "Family Secrets" trial, is speculated to be the "biggest mob trial in years." Experts are estimating that the trial will go on for about four months.
The case names three defendants who are also some of the believed top bosses in the mafia: James Marcello, 65; Frank Calabrese, Sr., 69; and Lombardo, 78. Other defendants include Paul Schiro, 70 and Anthony Doyle, 62. The defendants are charged with taking part in a racketeering conspiracy that included gambling, loan sharking, and extortion.
The case also attempts to tie 18 unsolved mob murders to the Chicago Outfit. One of these cases includes the deaths of the Spilotro brothers. One of Lombardo's friends and the Outfit's man in Las Vegas, Anthony "Tony the Ant" Spilotro, and his brother Michael were beaten to death and buried in an Indiana cornfield in 1986. This murder was made famous in the 1995 movie Casino when it was reenacted. Joe Pesci played the character "Nicky Santoro," which was based on Spilotro.
Halprin and his client have openly stated that Lombardo never ordered the killing of anyone, nor did he carry out any of the acts. Halprin explained that though Lombardo may have been linked to the mafia, it does not mean that he actually carried out any incriminating acts in this case.
Many critics disagree. But Halprin has grown accustomed to the lack of public support for his accused clients. "There's always someone who is inclined to say something, and basically, if I'm inclined to talk to them, I always say the same thing, which is: 'My job is to keep the cops out of your library.' And, 'I listen to what you're saying, but go through a red light one night after two drinks and hurt somebody, and then you'll be screaming about the Nazi cops who asked you whether or not you had some drinks,'" he said. "I long ago stopped taking exception to that."
Halprin's opinion of getting into the legal profession these days is that it's very difficult to find a job. "And if you want to be a criminal defense lawyer, it's extremely difficult," he said. Since many public defender jobs are dwindling, which is where many criminal defense lawyers get their feet in the door, it can be tough, but Halprin advises young lawyers to "try to survive."
"What happens traditionally in our office is people come here as law clerks, and they are willing to invest time in developing their own practice because they know that they are going to pick up business here," said Halprin.
Nevertheless, he encouraged law students to keep learning all throughout their careers. "The cases you lose are the ones you learn the most from, and the ones you win, you tend to take credit for because you were brilliant, as opposed to the facts were great and you did the right thing."