* Blackmailed Beth for her affair with Rick.
* Sabotaged Ava Peralta's divorce from Sandy.
* Drugged his aunt to make it appear as though they slept together.
* Faked his own death to disappear with his daughter.

Tom Pelphrey (September 2004 - February 1, 2007)
Sean Rademaker (September 1999 - January 21, 2000)

Jonathan was the son of royalty and this put him in a particularly precarious position. While still a child, he was placed in the care of Marissa and Alfred Randall. After suffering years of abuse at the hand of Alfred, he arrived in Springfield as the thuggish 'JB' to wreak revenge on the family that had abandoned him. He soon discovered Sandy Foster had assumed his identity. The two had known each other in the past and Sandy had left Jonathan for dead so that he could steal his identity. Jonathan set out to destroy his impersonator by planting evidence of his attempted murder. He then set about seducing his own cousin, Tammy, as part of his revenge plot. Once he revealed his identity, he rubbed taking her virginity in his mother's face and became a pariah.

Tammy would later warm to him after he saved her life in a fire, but they still fought after she opted for Sandy over him. When Jonathan's father returned to blackmail Lewis, they worked together but ended up betraying each other during an unexpected violent kidnapping and Alfred was killed. He sought comfort with Tammy and, after a long and erratic courtship which included setting several fires, they reunited in Cassie's barn only to be discovered by the entire family. Soon, Cassie had them arrested for arson and, while Tammy got off, Jonathan didn't and the relationship broke down.

He flew through a series of relationships, including a one-night stand with Lizzie that would come back to haunt him. When he discovered that Lizzie was pregnant with his child, he didn't want anything to do with it and pushed her to get rid of it or use it to get Coop. Later, when Beth tried to bribe him to stay away, he was only stopped from exiting by Josh.

Learning of the pregnancy, Reva tried to convince him to stay. After robbing her purse, he realized from the clues he discovered that she had cancer and confronted her. This became the source of their bonding. Meanwhile, Alan began trying to push Tammy and Jonathan together to keep him away from Lizzie. Seeing what Lizzie had to put up with, Jonathan became her ally against Alan and helped her escape from him. With Tammy, the three made an unusual couple and the strain only increased as the pregnancy went. Although he did propose to Tammy, Lizzie soon fell in love with him and he ended up marrying her to stop Alan from having the baby taken away from her. The fake marriage put a strain on his relationship with Tammy who finally encouraged him to try to make a go of it. However, despite his efforts, he is unable to commit fully to Lizzie and continued to run back to Tammy even after the baby is born. Finally, he had the marriage annulled and quickly married Tammy who joined with him to fight for custody. Within days of the marriage, she was killed in a hit-and-run ordered by Alan and intended for him. Furious, he first sought revenge by trying to burn Alan alive before plotting his own disappearance by faking his death. He and Sarah vanished together, leaving only Reva knowing that they are still alive.

Dinah_Marler (lovers)
Zoe (one-night stand)
Tammy_Winslow (lovers)
Elizabeth_Lizzie_Spaulding (one-night stand)

Richard Winslow (biological father - deceased)
Reva Shayne (mother)
Marissa Spencer Randall (adoptive mother - deceased)
Alfred Randall (adoptive father - deceased)
Marah Lewis (half-sister)
Dylan Lewis (half-brother)
Shayne Lewis (half-brother)
Prince George Winslow (paternal grandfather - deceased)
Unknown woman (paternal grandmother - deceased)
Sarah Shayne (maternal grandmother - deceased)
Susan_Daisy_Lemay (niece)
Roxie Shayne (aunt)
Rusty Shayne (uncle)
Cassandra_Cassie_Winslow (aunt)
Alonzo Baptiste (uncle)
Edmund Winslow (uncle)
Tammy Layne Winslow (cousin)
Roger Joshua Winslow (cousin)
William Richard Winslow (cousin)
June O'Neal (great aunt - deceased)
Olivia_Spencer_Lewis(adoptive aunt)
Sam Spencer (adoptive uncle)
Emma Spencer Lewis (adoptive cousin)

Sarah Randall (with Lizzie)