Roger Joshua (R.J.) Jessup was born in late 1998 to Cassie Layne. Although deeply in love with R.J.'s father, Hart Jessup, one thing stood in the way of them being a family--Hart's wife, Dinah. Although Hart deeply loved Cassie, Dinah was obsessed with keeping him with her. Wanting to confront a pregnant Cassie, Dinah tricked Cassie into getting into a limo and then sped off with the doors locked. Because of the snow storm (and because of her ranting), Dinah lost control of the car and drove into a snow bank. At that point, Cassie went into labor and Dinah was forced to deliver her nemesis's child. Tragically, mere months later, in 1999, the new family was torn apart when Hart died after being shot by Dinah who then went on the lam. Though devastated, Cassie was determined to put her life together and raise R.J. and her older daughter, Tammy, on the Jessup family farm. Later that year, while looking for her sister in San Cristobel , Cassie would meet the love of her life--Prince Richard Winslow. In 2000, Richard asked Cassie to marry him and that summer, formally adopted R.J. and Tammy. In 2001, the Winslow family expanded when Richard and Cassie adopted his nephew, William. Sadly, in 2002, RJ lost another father figure when Richard died in a car accident.

In 2003, a man who looked startlingly like the late Richard Winslow entered the Winslows' lives. This man was attorney Jeffrey O'Neill. Although he looked exactly like Richard, his personality was much different. Although Jeffrey professed to not like kids, he was able to calm RJ who was very apprehensive about his first day of school. From that point on, RJ developed a bond with Jeffrey, despite Cassie's dislike of the man. In 2004, RJ met a woman lurking around the farm. The pretty brunette told him that she was his imaginary friend. Weeks later, the Jessup farm accidentally went up in flames and RJ found himself trapped on the upper level. Luckily, his "imaginary" friend (none other than Dinah herself) arrived and saved RJ. Although Cassie was horrified to learn that Dinah had been around RJ, Jeffrey persuaded her that a trial would put unwanted strain on her family and she decided not to pursue the murder charges against Dinah. Later, Dinah saw RJ on the street and began talking with him about the fire. By asking leading questions, she got RJ to say that he saw Cassie's new boyfriend, Edmund Winslow, strike Jeffrey from behind and cause the fire when a lantern knocked over. (which Dinah had seen happen) Shocked, RJ relayed this Jeffrey, the night before Edmund and Cassie's wedding. Jeffrey, however, decided to keep quiet and the wedding went on as planned.

In 2005, Cassie learned the truth and wound up leaving Edmund. That same year, Cassie began a relationship with Jeffrey. In 2006, RJ lost yet another father figure when Cassie ended her relationship with Jeffrey. The only male constant in RJ's life was his Uncle Josh. At the end of the school year, when RJ got in trouble for fighting, RJ called Josh and not his mom. Months later, RJ was shocked when one day Hawk Shayne began comforting him about how confused he must be about his mother dating his Uncle Josh. Unfortunately this was the first that RJ had heard of it and he became upset that his mother was keeping secrets. After locking himself in his room for hours, RJ softened when Josh took him to Richard's gravestone and assured him that he would not be replacing his father. In 2007, RJ lost his big sister to a hit and run accident. Later, RJ gave Josh his blessing to marry Cassie and lent him his decoder to ring to make it official. Soon after, Josh was arrested for the attempted murder of Alan Spaulding and made a deal to accept a two year prison deal. Though he didn't know the particulars, RJ was furious to learn that Josh would be away for two years. Thankfully, Josh was released after only a few weeks in prison when the real shooter confessed. Later, RJ asked Josh for permission to call him "Dad". Months later, Josh and Cassie officially married.

Later, RJ learned that his mother was having surgery in the hopes that she could have another child. The day of the surgery, RJ visited Cassie and asked why she wanted another child. Wasn't he enough? Later, Cassie decided that instead of having a baby, she was going to reclaim custody of her son, Will. RJ had not seen his younger brother in years and was not happy about this potential interloper. When the private-tutored, smartly dressed Will arrived, RJ had no desire to be around him at all and became sullen when Cassie forced Will on him. He was also jealous of the time Josh and Cassie spent with Will. To better help Will adjust, the Lewises threw a party for him. At one point during the party, both Will and RJ went off. After playing gladiator with a pitchfork, RJ returned to the party but Will did not. Soon after, Will was found locked in the barn and implied that RJ locked him in. RJ told Josh that Will was lying but Josh didn't believed him. Mere days later, while downtown with Cassie, money from Beth Bauer's purse wound up in RJ's backpack. Again, RJ denied taking it. Believing RJ was acting out of jealousy, Cassie arranged for the two of them to spend the day together alone. From that point, RJ started to adjust to his new situation. On Christmas Eve, RJ and Josh ran into Reva while they were doing some last minute shopping at the mall. Suddenly, as they were in the stairwell, the power went out. Everyone was locked in the mall! Though RJ was scared, Reva and Josh calmed his fears and they ended up having a good time listening to Christmas carols, decorating a tree and even having a "snow" fight. Hours later, the doors opened and they made it to St. Mark's in time for Josh to read the Christmas story.

RJ spent the first part of 2008 frightened of his little brother though he couldn't say why. He just knew that there was something wrong with him. Without his knowledge, a series of events would prove RJ correct. One day while out skating with Will and Cassie, RJ unexpectedly skated on a dangerous patch of ice since he didn't see a sign warning of thin ice. (Will hid the sign) Thankfully, Cassie stopped him just in time. Because a disagreement about what to do with Will, things were extremely tense between Cassie and Josh. Cassie explained to RJ that Will was troubled and needed extra care and so she suggested that Josh and RJ move out of the farm so that Cassie could devote all her energies to Will. Then one day, while playing ball with Will in the woods, Will threw the ball onto the railroad tracks. When RJ went to get it, his foot became lodged in the tracks. RJ yelled for his brother to help but Will just eerily watched. Luckily Cassie arrived on the scene and rescued RJ just as a train was approaching. Later, Josh asked RJ if he thought Will acted mischievously on the railroad tracks. RJ refused to answer, only saying that he had to be careful what he said when Will was around. Not long after, Josh decided that he and RJ should move back to the farm. Though Jeffrey and Joshua had tried to send the boy away due to his behavior, Cassie continually resisted and was determined to help Will on her own. Later, during a game of baseball, Will was poised to hit RJ with the bat but Josh stopped him. Soon after, Will was sent away to a juvenile detention hall for good. Cassie apologized to RJ for being preoccupied with Will for the past few months and RJ admitted that he was glad that Will was gone.

Months later, RJ returned from summer camp to learn that sad news that Cassie and Josh were ending their marriage. Realizing that RJ had lost so many male role models, Cassie assured him that Josh would still stay a part of his life. Months later, RJ was saddened to learn that Cassie and josh were divorcing. Josh assured RJ that he intended to be a part of his life. Later, Cassie befriended a man named Cyrus who ended up performing various odd jobs around the farm. Eventually, a neighbor told RJ that Cassie and Cyrus were dating. However, when RJ asked about it, both denied it and Cassie insisted that Cyrus was just a friend. However, RJ had a hunch that there was something more and on Halloween, he told Cassie that approved of her dating Cyrus. Mere days later, Cassie shocked RJ by announcing that they were moving to Hawaii. Though RJ was reluctant, Cassie painted it as a grand adventure and he left town to start a brand new life with his mother.