In 1988, Jill found a bum on a park bench, cleaned him up, named him Rex Sterling, and paid him to romance Kay Chancellor. Rex was really Brian Romalotti, the ex-con father of Danny and Gina. What started out as a trick, ended up a wonderful romance. Kay found out who he was, but loved him so, she didn't care. They were married, and Rex signed a pre-nuptial to show his trustworthiness. In 1989, Rex's former cellmate, Clint Radison, showed up in town. Clint discovered Gina was Rex's daughter and started wooing her, and got her to marry him. But Clint was working on a new scam. He found a woman named Marge Catrooke who worked at a diner that was a dead ringer for Kay. Clint and his cohorts trained Marge to pass for Kay, then held captive Kay and her "ditsy" maid Esther. Meanwhile Marge posing as Kay drove Rex away, and he filed for divorce. Clint was now free to liquidate Kay's assets. But Kay's son Brock made a surprise return from his missions in India. Brock, with the help of Mitchell Sherman, discovered the ruse, and rescued Kay and Esther, who was pregnant by a one-night stand with Tiny the Plumber. Marge got to know Kay and also tried to help her to get away. Clint and his cohorts went to prison, but Marge was released as an innocent dupe, thanks to Katherine's intervention. Kay and Rex were reunited and re-married. After Clint was sentenced to prison, Gina turned to Brock. They became very close, but Brock was off on another of his missions to save the world before long.
It was early 2009, and Gina's ex-husband Clint got out of prison and returned to Genoa City plotting to get some of the Chancellor fortune. Clint found out that Katherine was assumed dead, and that Esther inherited one tenth of one percent of Kay's assets and Kayís half of the mansion. But he also heard the rumor that it was Marge who was killed, and Kay is trying to get everyone to believe she is still alive, so he instructed his cohort Roger Wilkes to woo Esther and marry her as fast as possible or he may have to do something to keep Kay from "coming back from the dead".
Clint kidnapped Kay just before the DNA results were due. Kay told Clint that she remembered kneeing him in the groin after she was freed from the first kidnapping, which temporarily convinced Clint that she was Kay and not Marge. But surprisingly, the DNA results between Kay and Jill did not match; which meant that Kay and Jill were not mother and daughter after all.
Then Roger and Esther's marriage plans were delayed when her daughter went into labor at the Abbott lake cabin and nearly died from loss of blood and septicemia. But a week later with Chloe and baby doing fine, Roger surprised Ester with a Justice of the Peace and impromptu wedding in her hospital room. After Jill found out about Ester's marriage, she gave Esther the results of Paul's investigation proving Roger was a bigamist who made a living marrying rich women, but Esther would not believe it.
Meanwhile back at the hotel, Kay's captor Annie was reading Katherine's book and admiring her. Kay began to convince her that she was really Katherine, and that Annie was being used by Clint and Roger; to which Annie admitted that she was the first Mrs. Roger Wilkes. Roger left the estate, and Esther followed him to the hotel where they were holding Kay. Roger walked in on an untied Kay, who had just convinced Annie to leave with her. Esther walked in and joyfully realized Kay was still alive. The three women were about to leave as Clint arrived, stopped and threatened them.
Meanwhile, Amber and Kevin realized that the first letter of every sentence of the note "Marge" left when she disappeared spelled out Clint. Clint met Amber hoping to convince her that he had witnessed Kay leaving town. As Clint left the bar, Gina spotted him and warned Amber and Kevin that he was her dangerous scammer ex-husband. Kevin and Amber tracked him down to the hotel where he was holding Kay and Esther, but Annie bluffed them into leaving. Kevin returned later, and Clint captured him too. Clint, Annie and Roger left Kay and Esther in the hotel room with a bomb rigged to go off, drugging and framing Kevin for it, and taking him along locked in the trunk of the car. Amber and Gloria arrived in time to untie Kay and Esther, the bomb went off, but no one was seriously hurt.
Meanwhile, between Kevinís claustrophobia and the drugs, he began to believe that Clint was his dead father Terrible Tom, which turned him into a whimpering child. Once Clint realized this, he took advantage of Kevin, coercing him to rob banks for him in a chipmunk head disguise. When Kevin successfully returned from his last robbery, a jubilant Clint had a heart attack and fell dead. Poor Kevin told him he was a bad dad and put him in the closet. A few days later Kevin pushed Amber inside with him when she tracked him down. Later, his body was found by Daniel and Michael when they arrived after Kevin and Amber had left.