In Never Gonna Give You Up, when there was a school play at Degrassi, Terri gets the lead role and Jimmy gave her great tips in rehearsal, while Rick gave some pretty bad tips. During the play, Terri takes Rick's tips and embarrasses herself in front of the entire school. Afterwards, Terri says she should have listened to Jimmy. This leads Rick to believe that Terri has more of a crush on Jimmy than himself. Rick retaliates by hurting Terri often and later apologizing, because of his 'fears of her leaving him for Jimmy', who was still single at the time. After dumping Rick, Jimmy tells Terri that he has her back just in case if Rick doesn't leave her alone.
In Don't Dream It's Over, Jimmy and his friends are shocked that Terri took Rick back and was inviting him on their road trip. However, while getting into a heated argument with Paige and Terri trying to comfort him, Rick, in the heat of the moment, pushed Terri to the ground which put her into a coma. Because of this incident, Terri transferred to another school.
In Mercy Street, Rick comes back to Degrassi which upsets Jimmy and his friends. Emma comes up and asks who is Rick. They explain that Rick is Terri's ex, he used to beat her, put her in a coma which had her transfer schools, and that he is in Emma's class. Emma and Paige then start a ribbon campaign to get Rick out of Degrassi, however the campaign turns into bullying.
In Time Stands Still (1), Spinner and Jimmy are seen bullying Rick and throw him into a dumpster. Rick then sprays paints an "X" on Spinner and Jay's car windows as revenge. After "Whack-Your-Brain" teammate Heather Sinclair becomes ill with mononucleosis before the competition, Jimmy was forced to become a contestant alongside with Rick. After Jimmy noticed that Rick isn't so bad after all during practices, and realized that the bullying had gone too far. After practicing for the Whack Your Brain contest, Spinner, Jay, and Alex confront Rick but Jimmy stands up for them and tells them to back off. While Jimmy, Toby, and Emma walk on by, Rick turns around and makes an "X" with his arms, proving that he did destroy Spinner and Jay's car windows. Meanwhile, Rick has told his mother that he, Emma, Toby and Jimmy have become inseparable. When Rick's team wins the finals at the Whack-Your-Brain Event, he is excited as it is being filmed and Emma gives him the trophy. However, yellow paint and feathers are dropped on him, leaving everyone to laugh at him.
In Time Stands Still (2), Rick briefly goes home, but returns to school with a gun and considers killing Paige, until she unexpectedly apologizes to him, unknowingly saving her own life. Rick then overhears Spinner and Jay falsely imply that Jimmy was behind the prank, knowing Rick was there and thinking that he would tell Mr. Raditch. Instead, Rick went to find Jimmy and the latter comforted him. He said that he had his back, when Rick said "You stabbed me in the back" and shot Jimmy in the back, leaving him paralyzed from the waist down.
In Eye of the Tiger, when Jimmy returns to school, everyone is thrilled, except for Spinner, who is feeling guilty. Jimmy is angry that he never visited him. When Jimmy tells Spinner that he wished that Rick would have just finished him, Spinner confesses his part in the shooting and says that he and Jay gave Rick the idea that Jimmy is the one who set the prank up on Rick. Jimmy then says "Then he shot me." Thus Jimmy ends his lifelong friendship with Spinner.
- Rick thought that Jimmy was trying to steal his then girlfriend Terri MacGregor away from him which was one of the things that began the abusive relationship.
- Rick shot Jimmy, which caused him to be paralyzed from the waist down and be put into a wheelchair.
- Rick also had a conflict with Jimmy's friends Spinner Mason and Paige Michalchuk.
- They were both a part of the Whack Your Brain Team.
- Rick thought that Jimmy set up the prank, which caused Rick to shoot him.
- Both were shot but Jimmy lived.
- They were both originally members of the Class of 2006 before joining the Class of 2007: Rick was held back in Mercy Street while Jimmy was held back in High Fidelity (2) and graduated in We Built This City.
- Rick thought that Jimmy's friend Ellie Nash was attractive.