A Harvard alum and magna cum laude graduate, Gerard became the college's third youngest professor at the age of 31. He went on to serve as prosecutor for the state of New York for 3 years, after which he made partner at his father-in-law's criminal defense firm. While Gerard was being considered for a seat on the federal bench, his teenage son, Timothy, fell in with a bad crowd and, suffering emotional abuse from his mother, got addicted to medications prescribed to him by his psychiatrist. Gerard separated from his wife and filed for custody, but since his wife came from an influential family, he was not able to. He eventually went so far as to kidnap Timothy to keep him away from his mother, for which he was disbarred and sentenced to 7-10 years at Federal Correctional Institution, Cumberland. Timothy hung himself a year later. Gerard continued doing legal work behind bars, serving as shadow counsel to politicians, CEOs, and high-profile criminals, including Reddington, who apparently consulted with Gerard before he turned himself in to the FBI against Gerard's strong objections.
Gerard locates the vault where Peter Kotsiopulos is keeping his embezzled money.
When Red puts together a team to exonerate Liz, he calls in Gerard as part of that team. Gerard helps them plan on how to kidnap Peter Kotsiopulos. Once they have the Director, Red demands Laurel Hitchin exonerate Liz in exchange for Red not taking the Director to the Hague and sends in Gerard to discuss the terms of the deal with Laurel. Eventually Gerard manages to negotiate a deal where Liz is exonerated publically for all but the Tom Connolly murder as Liz killed him in front of witnesses and it wasn't in self-defense. Instead, Laurel offers a plea of involuntary manslaughter with 3 years probation. Gerard privately talks to Red and convinces him to take the deal as it will keep Liz safe and out of prison and is better than Gerard expected them to get. Gerard later presents the deal to Liz who reluctantly signs it as she will no longer able to be an FBI agent though she can remain on the task force in a similar capacity to Red. Thanks to Gerard's deal, Liz is later able to walk free.
Red believes Gerard poisoned him and is destroying his organization. He was the only person who didn't come to the dinner, but sent a bottle of wine instead. However, upon testing the wine turns out not to be poisoned. The culprit seems to have been Dembe, who gave Reddington some whiskey.
Gerard is kidnapped by a bounty hunter, Philomena, who works for Mr. Kaplan. When he refuses to turn against Reddington, Kaplan leaves him bound to a lamppost, and he is arrested by the police.
Gerard negotiates a deal with Ressler whereby he will be released in exchange for not revealing Ressler's connection to Reddington and the Task Force.