In 2000, a few days before New Year's Eve, he met Shannon O'Donnell, who visited their bookstore. She wanted to wait for a tow truck because her car broke down and she found it too cold to wait outside. He joked that she might be a corporate hitman because of his father's resistance to the Millennium Gate project. When O'Donnell noticed that the rest of the stores were closed, Jason told her that they would never gave up, meaning he and his father would not sell their store to the people behind the Millennium Gate project.
Jason explained to Shannon what the Millennium Gate project was and listened as his father told Shannon why he was against it. When she noticed the fliers they wanted to distribute, Shannon offered to help if he would hire her. Jason joked that she would not be pleased, licking stamps for the next two days, whereupon she told him that they could use her computer. But Jason told her that his father did not believed in computers, and that they did not even own one.
When Henry told that her that he was not looking to hire someone, she once more asked Henry if he could hire her as she was on her way out. Jason saw his father hesitating and asked him to hire her, at which Henry told her that he could use some help.
The next day Jason watched his father explaining his resistance to Marci Collins of 3 Action News and telling Gerald Moss that the Millennium Gate was not Portage Creek's future but that of the people behind the Millennium Gate project. Afterward, his father triumphantly told him that they only had to stand firm until New Year's Eve. When Jason told his father that he had to go to school with the kids of the people who opposed Henry, he told him that the school would the first place that would be torn down. When Jason told his father that they said a better school would be built, his father questioned his loyalty.
Jason found Shannon's computer, which contained some neat games (according to him), and was playing Matrix of Doom when Shannon walked in. When Jason apologized for using her computer without permission, Shannon told him it was no problem and he offered her an cup of coffee. When asked were his father was, he replied that he went to Bloomington to get supplies; Henry Janeway was boycotted by the local stores, and that he was in charge of the store now. Jason asked Shannon if she had any children; she told him she never got around to it. When asked where his mother was, Jason told her that he never knew her; she died when he was very young. He thought that the Millennium Gate could be very cool and did not share all his father's ideas about it, and he listened to Shannon when she told him about the first landing on the moon. When Shannon asked if he had any heroes, he replied that according to his father, they were not living in a heroic age. He considered his father a kind of a hero. He found him pretty cool despite the fact that he sometimes was a pain in the ass. Their conversation was interrupted by the telephone; it was the first call in three days, but it turned out to be that the caller had the wrong number.
Henry Janeway returned with supplies around eleven o'clock, when Jason noticed the newspaper with a article about his father: "Local Business Owner Topples Gate". He was unpacking the supplies and storing them when he heard Shannon and his father starting arguing about the Millennium Gate project. When he returned, his father was helping Shannon packing her belongings and he told Jason that she was leaving. Jason was surprised about this; he thought she was staying with them, but his father insisted that Shannon leave. When Shannon had left the bookstore, an angry Jason took his coat and left also. Although his father shouted his name while crossing the street, Jason did not return to the store.
Later that evening, he hurried to the bar where Shannon had just finished her conversation with Gerald Moss and asked her if she would talk to his father. He refused to leave the store and a crowd had already gathered around it; even the police were there. When Jason told her his father would listen to her she told him that he would not. Jason asked her what Moss meant by "I will see you in Ohio" and what was wrong with Portage Creek. Jason thought she liked them, which she did, but she could not explain why she was leaving - it simply had not worked out between her and Henry Janeway. Jason watched her leaving the bar after she told him she was sorry.
Just before midnight, Jason was standing in front of the bookstore behind the police line when Shannon O'Donnell arrived. After looking at each other she walked up to the store and entered. Several minutes later, at 11:59, he watched Shannon and his father leaving the store, his father turning the open sign to closed, and he applauded together with the rest of the crowd and walked up to them. (VOY: "11:59")