The first case of helping someone was winning $15,000 by betting on horse races, knowing the outcome, then giving it to his blind friend Marissa so she can buy a guide dog.
Ultimately he stops the robbery by talking to the robber and after accepting his destiny, plans to send him a winning lottery ticket to help his financial troubles.
As rampant traffic jams prevent him from getting to the airport to stop a plane destined to crash, Gary tries to save a 6-year-old girl (Mae Whitman) hit by a car by getting her the necessary attention at the hospital.
A woman plans to abandon her baby and take her own life, so Gary attempts to reunite her with her parents, which fails and he starts running out of time to help her.
Gary stops the attack and Kurt is arrested, but Tommy out of fear hides in his treehouse with a gun and nearly shoots Bryce.
They arrive as the jury is about to declare a guilty verdict and while the judge initially refuses to even hear from Gus, after seeing how scared he is of Prosky, he listens to Gary.
While the judge refuses to allow Gus to testify, he declares a mistrial instead and asks the courts to arrange for Gary to never be called for jury duty again.
Gary has an out-of-body experience where he communicates with Rachel's spirit who convinces him to drop the paper and rely on faith as she apparently dies.
[1][2] Gary finds out that a greedy businessman wants to purchase McGinty's and an orphanage in order to demolish them and build a parking lot.
Gary and Chuck become involved with a night basketball program at a local church for inner city youth, where they meet a young nun named Sister Mary.
After learning that a leader of a white supremacist's movement, Darryl Foster, will be assassinated during a march, Gary begins to debate whether he should save his life or let him die.
Unfortunately, he finds out that he needs to convince a famous quarterback for the Chicago Bears, Joe Damski, to stop playing in order to avoid a serious injury.
After she hides in the backseat of his van, Gary must deal with Princess Sibella, who is believed to be missing after she runs away from her privileged and rigid lifestyle.This is an homage to the 1953 film, Roman Holiday, starring Audrey Hepburn.
Gary has to keep a soon-to-retire Detective Crumb from being arrested due to a blackmail investigation after he becomes the target of a ruthless District Attorney out to prove police corruption.
Gary foils the attempt and tries to warn Rachel, an Assistant State's Attorney, because the man is a recently released convict and she was the one who prosecuted him.
Gary reads in the paper that a pylon at a construction site drops and knocks over a nearby building, killing thousands.
Gary tries to prevent the disaster from happening only to get knocked out when he gets hit in the head and wakes up two days before the 1871 Great Chicago Fire.
[1][2] During a blackout which covers all of Chicago, Marissa attempts to save two trapped teenagers, while Patrick, a new bartender at McGinty's, helps Gary out.
He is assigned an attractive-but-surly agent, Toni Brigatti, to watch over him around the clock, which puts off Erica, whom he just got the courage to ask out and makes it difficult for Gary to fulfill his duties with the Paper.
Gary gets in the middle of a feud between a former Untouchable, Capone’s last living major gang member, who was just released from prison, and a retired T-Man who helped put him away.
Marissa's old friend, Julius, aka C-Roc, is in town for a CD signing and Gary has to prevent him from being killed at a concert.
When Gary refuses to prevent the next day's bad news, he winds up being forced to confront his own fate when he reads his obituary in the paper.
Federal Agent Brigatti, who recently transferred to the Chicago detective squad, takes on the case and attempts to track down Crumb's potential killer.
While Gary is able to prevent a robbery attempt by dangerous criminals, he is unable to convince the local sheriff that the convicts are hiding out in his little town.
It turns out that the sheriff, Joe, is an envious old high-school classmate of Gary's who decides to throw him in jail for causing a ruckus.
Real Life Filming Location: Navy Pier[70] Gary saves Detective Armstrong's wife from drowning at a gym.
Chuck comes for a visit and offers to take Gary to a Cubs game where a promising rookie, Pedro Mendoza, is going to play.
Gary and Detective Toni Brigatti have to pretend they are a couple for an extended amount of time in effort to catch a jewel thief, while also searching for the gas leak that will cause a ship to explode on Lake Michigan.
Gary joins an amateur acting troupe where he finds former detective Crumb participating and later learns that the theatre will be burned down by an arsonist.
Gary ends up pretending to be engaged to her while she dodges an INS agent and looks for the man she loves, Nigel, while her brother plans their wedding.