Jack is babysitting Zack while the Vassers are out on the town. They are playing and Zack lets it slip about dad's big bag of money in the closet. Of course, cop Jack thinks the worst and takes one of the bills as evidence.
Katie and Dan come home and she tells him that she wants to go back to work as a television news reporter. Dan is about to take out the recycling when he wormholes back to 1999. He wakes up in the back of a guy's SUV and the guy freaks out and pulls over to throw Vasser out, but the car is being tailed by some Asian gangsters who riddle the car with bullets as Vasser and the guy take off. The gangsters find Vasser's press credentials from the San Francisco Register.
The guy has been shot in the gut so Vasser rushes him to the hospital. The cops and the district attorney's office show up and shuffle Vasser out of the room. The guy is the key witness in a court case against the gangsters who are importing heroin.
Back to the present day, Katie gets a job offer from her old partner on the news team and she says she has to talk it over with Dan and that she'll get back to him.
In 1999, Dan is wondering why he hasn't gone Back to the Future and Livia shows up to help him figure out that he needs to protect his 1999 self from the gangsters since they know he's a reporter and they must now think that the witness guy must have told Vasser everything. Livia and Dan go to his 1999 apartment and find the place empty but trashed. The gangsters have turned the place upside down. They clean the place up and get out just ask 1999 Vasser and Katie and her old news partner show up.
Jack gets a visit from the feds in 2007. The bill he took from Dan has been flagged as being one of the serial numbers from the Dylan McClane heist back in 1974. The feds want to know where it came from and how it's in such good shape after all these years. Jack brushes them off and promises to get back to them once he's completed his investigation.
1999, Livia has a borrowed car, so she and Dan hide out and watch as Katie and her news team partner leave 1999 Dan's place. They are going to stake out Vasser's place until the witness has a chance to testify in court in the morning, but 1999 Vasser isn't going to make it easy on them by staying home. He's got a poker game to get to. 2007 Vasser and Livia tail him to the game, but the gangsters are also on his tail.
1999, Vasser leaves the poker game, but he's drunk and the gangsters are about to kill him when 2007 Vasser tries to stop him. They get into a fight, luckily the alley is dark so 1999 Dan can't see that's it's 2007 Dan trying to kick his ass. 1999 Dan gets knocked out and 2007 Dan and Livia throw him in the car and take off
Back in present day, Katie has an interview with her old partner who's now in charge of the newsroom at their old television station. He offers her a job and she accepts it.
In the past, Livia and Dan put 1999 Vasser to bed. Dan realizes that he's not supposed to be asleep. He was just supposed to go home to get his bankroll and return to the game where he would eventually be pulled out by Katie – thus beginning their relationship. So 2007 Vasser has to pose as 1999 Vasser and get back in the poker game, but he doesn't have any money and the bankroll he was supposed to come home to get was stolen by the gangsters who trashed his place earlier that evening.
Livia, who seems to be able to control when and where she goes in time, goes back to Dan's 2007 house and gets the money out of the closet and it's a good thing too, because Cop Jack shows up and drags Katie into the closet to show her the money Dan has hidden there, but it's gone. Katie flips out on him and he gets angry and leaves.
In 1999, Dan is desperately trying to find $10,000 to buy in at the poker game and he thinks the only way to get it is to steal it back from the gangsters. He's about to go after them in their car outside his apartment when they get a call and take off. Vasser tails them to the hospital where the witness is being transferred. The gangsters try to take the witness out, but Vasser stops them and they get arrested and the cops find the money before Dan can get it. Just then, Livia shows up with the high jack money just in time and Dan goes and plays poker and drinks shots. Katie's new partner is in the game too and he sees Dan spiraling out of control and calls Katie to come rescue him. She drags 2007 Dan back to his 1999 apartment and 2007 slips away and she finds him asleep in his bed. He wakes up while she's watching him and they share a moment. Outside 2007 Vasser thanks Livia for showing up with the money and literally saving his life. He's talking about his life with Katie and Zack and that is touching.
The feds put the screws to Jack, who's done with his brother and his ex-girlfriend. They want to know where the money came from and Jack tells them that he got it from his brother.