Bobby Donnell

His father, Stephen Donnell, was a janitor in a corporate law firm. Bobby's relationship with his father is mentioned throughout the early seasons of the show to imply, in various ways, the reason why he is opposed to the firm's expansion. Seeing the way the "blue chip" lawyers treated his father was a motivation to be a lawyer. Bobby was raised in a Roman Catholic household and remained a devoted, if often conflicted, Catholic throughout the series. His parish priest would be a lifelong friend and counselor for him, especially in the days following the death of his mother, something that affected Bobby deeply. Donnell obtained his J.D. from Suffolk University. Growing up, Bobby also met and befriended Jimmy Berlutti.

Throughout the series, Bobby is conflicted between what he perceives as his duty as a defense attorney and the reality that many of his clients escape justice on either legal technicalities or official errors and even misconduct, which testifies to his prowess as a defense attorney but haunts him as a human being. On more than one occasion, including in chambers with an equally disillusioned judge, Bobby has vented against the corruption of a legal system he once admired.

Bobby was secretly involved with his colleague Lindsay, but ended this affair in order to be with DA Helen Gamble, with whom he had had a love/hate relationship. This soon fizzled out, however, and he eventually got back together with Lindsay, with whom he later married and had a son. He also briefly dated Ally McBeal, who appeared in a crossover episode from the show named for her-even though The Practice and Ally McBeal appeared on different networks, both shows were produced by David E. Kelly and both were set in Boston. Bobby also got a surprise when Judge Roberta Kittelson admitted to him privately that she had erotic dreams about him, but Bobby's reborn love for Lindsay precluded him from pursuing an intimate relationship with the attractive judge.

Around the time Lindsay became pregnant, a psychopathic pseudo-serial killer named William Hinks began threatening her. Bobby arranged for one of his former clients to intimidate Hinks in the hopes of scaring him away from Lindsay, but instead, the client ended up cutting off Hinks's head and placing it in the freezer, an apparent homage to Hinks's brutal reign of criminal terror. Upon discovery of the crime, Bobby was arrested as a co-conspirator in the murder.

Bobby and Lindsay's child was named Bobby, Jr.; he was last mentioned by Lindsay, who said she would retain custody of him after they divorced. The marriage was threatened almost from the outset by the inner conflicts Bobby and Lindsay suffer as a result of their professions as defense attorneys, their often psychotic clients, and their inability to communicate to each other those conflicts and the doubts they provoke in themselves.