1997

He was a crazy old man who believed that God talks to him "when he's in town". Rebadow was beat up by Kenny Wangler, and believed that he never had spoken to God, and in fact was hearing his own powers of reason.

1998

Rebadow's new cellmate, Agamemnon Busmalis, began to dig a tunnel in their cell, and Rebadow helped him. They were discovered by Mark Mack. Mack had his friend, Officer Metzger, switch their cells, and Mack was killed when the tunnel collapsed on him.

1999

Rebadow met his son and grandson for the first time shortly after being diagnosed with diabetes.

2000

After Busmalis escaped, Rebadow was approached by Enrique Morales. Morales forced Rebadow to kill Raul Hernandez, and after the murder Rebadow became obsessed with murder. When Busmalis was caught, Rebadow tried to kill him. He was stopped, and spent some time in the hole. When he returned, he apologized to Busmalis, then collapsed due to a brain tumor. Rebadow survived the operation and returned to Emerald City, and he and Busmalis remained friends.

2001

Rebadow was Busmalis's best man at his wedding.

2002

Rebadow learned that his grandson has entered the final stages of leukemia, and he began an obsessive search for a cure. He asked Officer Dave Brass to purchase a lottery ticket for him. When they won, Brass claimed the money and left his job, as well as a broke Rebadow, far behind. Rebadow's grandson finally died, and he was allowed to go to the funeral. Then Brass returned with the intention of giving Rebadow his money to save his grandson.

2003

A grieving Rebadow began working in the library with intentions of helping out the new librarian in any way he can. Rebadow and the nice librarian lady, Stella Cotta, discussed their mutual passions for reading. Rebadow tried to get inmates to read a book, but not even Busmalis would help him out. Rebadow found himself becoming atracted to Stella. He spoke to Miguel Alvarez, who was distressed that his girlfriend wouldn't come and visit him. Rebadow also spoke to Norma Clark, who was distressed that Busmalis wouldn't even talk to her. Rebadow tried to talk some sense into Busmalis, but it was no use. Rebadow, however, learned that librarian Stella had breast cancer and became incredibly depressed. Stella learned of Rebadow's grandson (the dead one) and confronted him about it. He refused to talk about it, and Pablo tried to force Rebadow to listen. Stella got Pablo to leave. Rebadow still refused to talk to Stella. While Rebadow was going through Unit B delivering books, Pablo Rosa confronted him about his rude behavior toward Stella the librarian. Rebadow returned to the library and spoke to her. She accepted his forgiveness, but decided that she did not want a relationship with him. Rebadow was impatiently waiting for news of how Stella's surgery had gone. As he was delivering books in Unit B, he saw Pablo (Stella's project) stab an inmate in the neck. That night at count, McManus informed Rebadow that the surgery was a success.