As a boy, Kevin and his brother Joey's dad, Joe Riley, died. Clint adopted them when Clint married their mom, Viki Lord Riley Buchanan. In 1991, as a teenager, Kevin's first real love was Stephanie Hobart, the niece of the hated Carlo Hesser. Because of Carlo's hatred for the Buchanan, he ended the relationship. Right after that, Kevin started a little love affair with LeeAnn Demerest Buchanan. They stayed together even though Max Holden had a passion for Lee Ann. Once Lee Ann thought Max had fallen for Luna Moody, Lee Ann and Kevin made love. When Kevin found out that Lee Ann was pregnant in 1992 they eloped. Kevin and Lee Ann's marrige just wasn't to be. Lee Ann had grew very close to Jason Webb. Kevin got a divorce, and Lee Ann went to Texas and took Duke, Kevin's baby with her.
Kevin started to grow very close to Rachel Gannon. Rachel's father Hank didn't help much though, he didn't like their friendship at all. While studying at Llanview University, Kevin was charged with raping Marty Saybrooke. She also went to the college. They soon found out he didn't do it when their main suspects were Todd Manning and his buds. It turned out that they had done it. Later in 1994, Rachel and Kevin were going to move in togeher, but when Kevin went to Texas to go visit Duke, Rachel and Dr. Ben Price started their own little romance. Kevin ended the friendship between him and Rachel.
Kevin wanted to to what his parents had done and become a reporter. While starting his new job, Kevin dated Andy Harrison. They dated until Kevin went to London in 1995, on assignment. That fall, Kevin ended their relationship in a letter.
Kevin came back to Llanview in 1996, and became an investigative reporter. That's where he met his rival reporter Cassie Carpenter. Cassie was married, but that really didn't matter to Kevin, he wanted a romance with her from the start. Cassie kept resisting him, and told him to get someone else. He soon did, Téa Delgado. That made Cassie very jealous seeing Téa with Kevin. Finally in 1997, Cassie couldn't resist anymore and they made love. Cassie left her husband Rev. Andrew Carpenter and married Kevin.
Later in 1998, Kevin and Cassie hired a nurse named Barbara Graham. She was supposed to take care of Cassie's father, David, who was very sick. She soon fell in love with Kevin. Kevin and Barbara were trapped together in a cellar when Todd was holding everyone hostage at the Buchanan lodge. They couldn't resist each other and they made love. Kevin regretted it so much. Cassie soon found out about it, and she was mad! One night Barbara tried to kill Cassie for interfering with her and Kevin. She tried to shoot Cassie, but accidentally shot and killed Kevin's cousin, Drew. Cassie was shot, too and she was paralyzed. Cassie started to go insane after that. She held Barbara hostage. Kevin soon found her. Cassie was shipped of to Switzerland and their marrige was annuled.
In 1999, a woman named Grace Davidson arrived in town. Now they call her Grace Davidson, it had to do with her being abducted as a child by the mob. She charmed her way into Kevin's life and they had a romance going, but then Gretel Rae Cummings came to town. Rae was looking for her husband, who had cheated on her with a younger woman. That woman was Grace. Rae wanted to ruin Grace's life for having an affair with Rae's husband, Daniel. Rea tried to talk to Kevin. She wanted Kevin and Grace to no longer be a pair. It made Kevin mad a little when he found out, but they are still together. Kevin and Grace, a fellow reporter are covering the Lindsay Rappaport trial. It is a big thing in the media and they are trying to get the better story.
Kevin and Grace were getting a really good relationship going, and Kevin asked her to marry him. Then Grace was killed by a freak accident involving Rea Cummings and Asa Buchanan. Kevin then had serious grief, and soon got addicted to alchohol. With help from his mother, Viki Lord Davidson, his brother, Joey Buchanan, a friend Skye Chandler, and Kelly Crammer he got well again. On New Years Eve night Kelly was trying to help Kevin get over Graces death, and also help him to stop drinking. They got closer and they kissed, and almost ended up sleeping together, but stoped themselves. After that they had a hard time to be near eachother with out getting feelings toward one another, and since Kelly was going to get married to Joey, Kevin's brother they couldn't risk being near eachother, and accidently doing something they would regret. One day Kelly and Joey went off, and got eloped right before Kevin could tell Kelly that he wanted to be with her even if it broke Joey's heart. Kevin was heart broken. He decided after that that he should just keep his true feelings to himself.
Then Kevin and Kelly started working against Asa, and using the Sun and the Banner to make him drop the charges against Will Rappaport. The more time Kevin and Kelly spent together the closer they got. Finally they both admited their true feelings for eachother, and they were together. One day they decided to tell Joey about them. Joey was heartbroken, and Kevin and Kelly knew what they had done to him, but they wanted to be with eachother. Joey for awhile tried to hold on to Kelly, and get back together with her, but nothing worked and Kelly and Kevin stayed together. Joey and Kelly got divorced, and Kevin and Kelly finally made love for the first time on New Years eve. Later that year Kevin went to go visit Duke in Texas. He is still there now.