A young Irish woman loses her chance at a million dollar lottery when Gary swipes her dollar that she was going to buy the winning ticket with. To repay her he ends up caught up in a wild scheme that has them pretending to be engaged while Kate looks for a man she loves.

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Gary travels back in time to 1929, and is the proprietor of a speakeasy at the location where McGinty's is currently located. He must try to prevent the St. Valentine's Day Massacre.

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Gary finds out why he was chosen to receive the paper.

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Gary must keep rescuing an accountant who is determined to become a bounty hunter.

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When Chuck returns to Chicago to get married, Gary recognizes Chuck's bride as Amber, a jewel thief. She is now calling herself Jade. Gary confides in Marissa who tells him that he must inform Chuck. Gary confronts Jade, who tells him that she truly loves Chuck and that she is really Jade. He decides not to tell Chuck what he knows. The next morning's paper says that a large diamond will be stolen from an auction. Gary and Marissa throw a private rehearsal dinner for Chuck and Jade to keep Jade there while the theft is suppossed to happen. Jade hires two female strippers to handcuff both Gary and Chuck. She then leaves and steals the diamond. When she returns to her apartment Gary confronts her. Jade tells Gary that she had to steal the diamond because it was once a national treasure of her country. Gary doesn't believe her story. He takes the diamond from her and puts it into the curator's mailbox with a letter warning them to tighten security.

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Gary loses his sight while he is trying to prevent three teens from being blown up by an old cannon ball. While at the hospital, Gary meets a yong kid named Nate Calvin, whose mother is ill. The next day, without being able to see, Gary must save Nate Calvin, who is trapped in an abandoned building.

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While at the theater, Gary runs into his old friend, ex-Chicago police detective Marion Crumb, who joined the Shakespearean troupe after the play's director, Bonnie Rousseau, convinced him to pursue his natural born acting talents. While pooling the cast's money to put on the production, Bonnie recruits Gary to replace one of the leads who has had an accident. As Gary throws himself into his new role, the production is threatened -- first by a producer claiming to have rights to the theater and then by an arsonist. As Gary and Marion work together to put out all the fires, damaging evidence arises against Bonnie that reveals she's a scam artist. With hours left before show time, it's up to Gary to stop Bonnie from deserting her devoted troupe -- or else it's curtains for everyone.

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While stealing cars for a chop shop, Jose (Joey) encounters Gary, who is brought in by police to ID the teenager in a criminal lineup. When Gary realizes that Joey is Miguel's little brother, he denies knowing him in order to protect his friend. Although Joey promises Gary that he will go straight, his accomplice pressures him into pulling another job, a heist in which the owner of the car is shot and Gary is taken hostage. While trying to convince Joey to give up his life of crime, Gary is wounded by gunfire and left to ponder whether or not he should have acknowledged Joey's involvement the first time around before people were seriously hurt.

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The former recipient of the New York paper decides to relinquish his duties by turning over the next day's news to his friend Clams, but the paper suddenly stops coming after Clams meets with a mysterious man asking questions about his satisfaction with his special subscription. When Gary is involved in a similar meeting, Clams warns him that he too could lose his paper if he makes any wrong decisions. Desperate to get his own paper back, Clams steals Gary's edition so he can convince the powers-that-be to give him another chance. But even as he tries to make amends, Clams continues to abuse the paper and winds up putting the life of a down on-his-luck computer genius in jeopardy. When Gary reads that Clams and the computer wiz will perish in a dangerous explosion, he must race to save their lives before it's too late.

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After saving a playmate of Nikki's and then preventing her from being injured in a school bus accident, Gary meets the tough-talking 13-year-old and learns that she also knew about the accidents before they almost happened. While most would consider Nikki's clairvoyance to be a gift, she is racked with guilt because she was unable to save her own parents from dying in a car crash three years earlier -- an event Gary also failed to stop.

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While out in the snow, Gary encounters two men, Earl Camby, a reformed criminal who now devotes his life to helping those less fortunate than himself, and Cliff Mourning, a sleazy motel operator. As Gary tries to save Earl's life when a building collapses on him, he reads that Cliff is going to succumb to a heart attack. Torn between leaving Earl alone to die while he saves an ungrateful human being, Gary contemplates a decision that could ultimately tie the two men's lives together.

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Although Crumb cautions Gary that Rose may appear sweet and innocent but is probably trouble, Gary ignores his warning, even when evidence surfaces that she has a criminal record. When he believes her explanation that an old boyfriend is after her, Gary agrees to loan Rose $25,000 to get rid of him and is stunned when she suddenly runs off with his money.

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When Gary ignores Marissa's repeated requests to help her manage the workload at McGinty's, the paper plays a dangerous trick on him: he reads that his friend will be struck and killed by a car. Gary finds himself in a daily replay of the same 24 hours, � la the film Groundhog Day, when, unable to save her the first time around, he awakens to find history repeating itself -- twice. Failing to prevent the accident a second time, Gary is given one more chance to learn from his mistakes so he can save Marissa's life.

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With Gary as her guide, Rebecca becomes renowned for her accurate forecasts, until the paper shows up at his doorstep one morning without a trace of the next day's weather. Searching for a way to save his budding relationship, Gary reads a story in the paper about a group of construction workers who are killed when a gale force wind knocks over a Christmas tree they're trying to put up. Racing to the television studio, Gary attempts to get Rebecca to warn the workers about the potential disaster. Meanwhile, Gary's old friend Uncle Phil (guest star Fyvush Finkel, reprising the role) winds up in a series of jobs and disasters that Gary must prevent.

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When Gary's own investigation leads him to one of Scanlon's informants, he learns that at the time of Scanlon's death, the reporter was about to break a story on a murder-for-hire ring. With the help of Sun Times photographer Miguel Diaz, Gary obtains a printout of Scanlon's notes for his story that identifies six murders that were made to look like accidents. Meanwhile, Detective Brigatti uncovers some evidence of her own, which proves Gary's innocence and implicates someone with whom she works closely in the department. When Brigatti is subsequently taken hostage and about to be murdered, Gary must save her before the real killer sets him up a second time.

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When Frank Scanlon, a Chicago Sun Times columnist famous for his exposes, meets Gary during one of his daily saves, Gary piques the interest of the reporter, who believes that the rescues are more than coincidental. Intent on investigating Gary further, Scanlon demands that Sun Times cameraman Miguel Diaz hand over the confidential file he's been collecting on Gary. Meanwhile, when Gary reads in the paper that Scanlon is about to be murdered, he rushes to save him but the paper lists the wrong time of death - leading Gary to be found at the scene by police and subsequently arrested. Mounting circumstantial evidence even has Detective Toni Brigatti convinced of Gary's guilt. After escaping his arraignment, with Marissa's help, Gary becomes a fugitive desperate to find Scanlon's murderer.

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While struggling to find a way to tell his boss that he's leaving McGinty's for good, Patrick thoroughly frustrates Gary by following him around all day and triggering a host of potential disasters. When Patrick's actions culminate in an explosion at a Halloween rave party, Gary instructs him not to move a muscle - a directive that backfires when Patrick attempts to help and winds up in a life-threatening situation.

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While covering the opening of a local pickle factory, Miguel winds up in the middle of one of Gary's saves, when he falls head first into a barrel of kosher dills. After Miguel's pickled puss winds up in all the papers, he loses his job and must take a position at a museum, where he's forced to photograph uncooperative school children. When Gary reads that one of the kids at the museum will be injured, he races to prevent the tragedy - only to cost Miguel another job. To make matters worse, while at the museum, Miguel inadvertently takes a photo of Bruce Bryce a vicious criminal thought to be dead. When he realizes he has evidence that could potentially get him his newspaper job back, Miguel heads over to the Sun Times with the film. But Bryce tracks him down and threatens him with bodily harm if he doesn't hand over the photos. With Miguel's life in jeopardy, Gary must figure out how to save him before his days as an inquiring photographer are over.

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As Brigatti carries out her plan to entice the thief with an expensive diamond pendant, her relationship with Gary grows more personal since they are forced to spend several days and nights together. When it appears that the case has been solved, Gary reads that the diamond will turn out to be a fake -- putting Brigatti's career in jeopardy. Armed with tomorrow's news, only Gary can save Brigatti's job by finding the true thief and returning the diamond to its owner.

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After Gary reads that Pedro Mendoza, a rookie pitcher for the Chicago Cubs, is going to pitch a no-hitter. Chuck convinces him to attend the game. But when Chuck inadvertently changes the course of the day's events by taking a cab meant for the ballplayer, the story is replaced by an item about the pitcher being injured while on his way to Wrigley Field. After preventing Pedro's impending accident, Gary races to protect a restaurant owner from being seriously injured by a loan shark. When it turns out that the man is Pedro's brother, Gary and Chuck find themselves in the middle of another potential tragedy. They read that the brother will be killed and the ballplayer's arm will be broken by the menacing thugs. With only a few hours left, the duo must try to save the day so Pedro can pitch the game and still make the history books.

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Gary meets a man, Sam Cooper, that also receives tomorrow's paper (the New York Daily). However, unlike Gary, Sam hires others to complete the rescues and uses the paper's knowledge to make money.

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