Attorneys for former Chicago Alderman Ambrosio Medrano are scheduled to give their opening statement in federal court Tuesday morning but this isn’t the former alderman’s first time facing bribery charges and it might not be his last.

Medrano already did prison time in the late 1990s for taking a bribe while an alderman. Now, he’s on trial for trying to pay a bribe to a public official in California.

Prosecutors say Medrano thought the bribe would win him a contract mailing out prescription medications for the Los Angeles county government. The problem for Medrano is that he was communicating not with a dirty bagman but with an FBI mole; and the public official didn’t actually exist, he was a fiction created by the FBI. Prosecutors say they have emails, recorded conversations, and the testimony of the informant to prove their case.

Medrano’s attorneys are expected to make their first pitch to the jury Tuesday morning. The former Alderman is also facing public corruption charges in a third case that is tentatively scheduled for an October trial.