Prince Richard Winslow was first introduced when Reva shayne traveled to San Cristobel to try to remember her past. Reva could not account for five years of her life and was certain that the answers were on the island of San Cristobel. Reva was right. It turned out that after her car crashed in the ocean Reva somehow ended up in San Cristobel. With no memory of who she was, she took the name Catherine and ended up marrying Prince Richard Winslow, San Cristobel's ruler, and bore him a son, Jonathan. Hopelessly in love, Richard was devastated when Catherine disappeared and took their son with her.

Forward years later, to 1999. By now, Richard had had finally put Catherine behind him and was engaged to Olivia Spencer. However, when Reva came to San Cristobel , she was arrested. When Richard saw Reva again he threatened her and demanded to know where his son was. Although she tried to explain that she had amnesia for years, Richard didn't believe her and threatened her life if his child was not returned. When Richard showed Reva a portrait of his wife, "Catherine," Reva was so shocked that she fainted. Once she came to, Richard believed her and told her that some San Cristobel fisherman had discovered her in the waters offshore and had brought her back to the hospital there. Richard had eventually brought her back to the palace to recover, and they fell in love, married, and had a son. Reva told Richard that she wanted to stay with him and help find out what happened to their son. Richard made plans to take her to all of the places that they used to go when she was Catherine to help her regain her memory. Throughout the summer, Reva began to remember all of the love that she had felt for Richard and all of the happy memories they shared together. Later, Olivia told Reva that Jonathan had died, and that he was buried in the back of her house. Reva broke the news to Richard that their son was dead, and that Olivia had hidden the truth from them for all of these years. They went to find the grave marker so that they could say their goodbyes, and while there, they discovered a child's swing. Olivia didn't have any children, so their suspicions arose. Reva, who had been planning to return home, vowed to stay in San Cristobel and help Richard get to the bottom of what happened to their son. When Richard confided in Reva that he was still in love with her, Reva declared her undying love for Josh Lewis, her husband. Meanwhile, Reva began to have memories of how Richard's evil brother, Edmund, had treated her badly when she was living in San Cristobel. She remembered Edmund threatening her son's life, and remembered that she gave the baby to Olivia to keep safe. Olivia admitted to Reva that Jonathan was very much alive and being raised by her sister, Marissa, and her husband. It soon became clear to Reva that her life was in danger, and she joined forces with Olivia to prove to Richard that Edmund was responsible for the disappearance of their son.

In the meantime, Richard planned a masquerade ball to celebrate the day that he and "Catherine" had married. Reva had since developed closeness to Richard, and agreed to be "Catherine" for him one more time on the night of the ball. At the ball, Reva asked Edmund to meet her in private to talk about Richard and Edmund took her captive at gunpoint. At that point, Josh and others arrived to rescue Reva from the island. Eventually, Richard and the others found Reva trapped in a cave filling with water. Luckily, Josh was able to save her just in time. Richard and Reva were finally reunited with their son, but when it became clear that Jonathan's life was still in danger, Reva asked Olivia to take Jonathan away again so that he would be safe. She left the island with Josh, leaving nothing behind for Richard but a goodbye note. Furious that Reva sent Jonathan away without even consulting him, Richard followed Reva to Springfield and eventually tracked her down to Cross Creek. In a fit of rage, Richard tried to kill Reva for what she had done, but soon things turned passionate. Before their passionate kiss turned into something more, Josh and Reva's sister, Cassie, arrived. Later, in January 2000, with Selena Davis's help, Reva broke into Olivia's room at the boarding house and found Jonathan's phone number. She called him and, pretending to be doing a survey, was able to get his new address from him. She immediately flew to San Cristobel to give the address to Richard. Reva and Richard traveled to the Randalls and once they saw how happy Jonathan was, they realized that it was best not to tell him who they were, and to let Marissa and Alfred continue to raise him.

In the midst of all this angst regarding Reva, Richard found himself being befriended by her sister, Cassie Layne. Then one day when Cassie was in San Cristobel , there was an incident at the palace with some angry citizens. Knowing that the citizens of San Cristobel demanded that he produce an heir, and impressed with Cassie's charm, he asked her to become his wife. It was strictly a business agreement. Cassie would produce an heir and Richard would solve her money problems. Cassie moved into the Palace and Richard began to fall in love with her. Later, when she contracted the measles and was told she may not be able to get pregnant, she offered to back out of their deal but Richard insisted on marrying her. When a series of accidents at the Spaulding Enterprises's construction site in San Cristobel caused problems for the monarchy, Cassie was determined to find out who was responsible and convinced Richard that an investigation was necessary. So, with the help of her best friend, Harley Cooper, they went to Galveston, Texas where the construction crew was now staying. They posed as a married couple, Dwayne and Stella Owens, got jobs at the Red's bar and were forced to live together in very small quarters while they fought their feelings.

When they were exposed, a guy named Gill threatened Cassie with a knife but Richard and his friend Noah Chase saved her while Gill fell onto his own knife and went to the hospital. At this time, Cassie and Richard learned that Edmund was the saboteur. The pair then returned to San Cristobel and finally admitted their love for each other. But Cassie wanted her wedding to be old fashioned, right down to the tradition of not making love until their wedding night. Meanwhile, Danny and Michelle Santos went on the run from the police because Michelle was falsely convicted of murder. They ended up in San Cristobel and phoned Cassie for help. Wanting to return the favor after they helped her find Reva over the summer, Cassie hid them in the palace but didn't tell Richard about it because she feared that hiding the fugitives would compromise his position. However, soon Richard learned the truth and though he was ready to turn the two in to the police, Cassie persuaded him to help the pair and he gave them two weeks to clear themselves. Meanwhile, Edmund found pictures of Cassie's stripping days and displayed them for the public to see. Although she considered leaving San Cristobel so that Richard could find a more suitable wife, Cassie loved Richard too much, and told the people of San Cristobel her story and let them decide if she should be princess. To her surprise, the people supported her.

Later, when Cassie's ex-husband, Rob, learned of Cassie's engagement to Richard, he reappeared, and told a shocked Cassie that she was still married to him. Apparently, Rob never signed the divorce papers. He offered her a divorce for a price. Cassie tried to bribe Rob into signing the papers, but he only got greedier and demanded more money. Unfortunately, he was almost executed when Edmund faked an execution order to publicly humiliate Richard so he could gain control of the monarchy. Though Richard rescued him, an angry Rob now demanded $ 1 million and a day alone with his daughter, Tammy. Against her better judgment, Cassie agreed. Later, Rob told Richard that he'd let him adopt Tammy in exchange for $ 18 million. When Richard refused, Rob kidnapped Tammy to Springfield. Desperate, Cassie and Richard turned to Reva for help and they came up with a plan. Reva met with Rob and pretended to be on his side. When Reva's recording device fell to the ground, Rob he got into an argument with her and accidentally knocked Reva out. She was apparently unconscious and, afraid that he'd be arrested, Rob signed the divorce papers and granted custody of Tammy to Richard, then hurried out of town before the imaginary ambulance arrived. Finally free, Cassie and Richard married in a fairy tale wedding.

After the wedding, Richard and Cassie were elated to learn that she was pregnant! Their happiness, however, was marred by Edmund's schemes to make Richard believe that Cassie was unfaithful. Fortunately, Richard realized that Edmund was setting Cassie up and denounced Edmund. Then Richard discovered a deep family secret: he was NOT the legitimate heir to the throne; Edmund was! It seemed that Richard's mother was not Princess Charlotte but an unknown lover of his father's. When Richard made this news public, Edmund took the throne. Convinced that Richard would take the throne from him, Edmund went after him and Cassie and tried to get them off the island. Tragically, Cassie lost her baby as a result when she ran away from one of Edmund's gunman and caused a car accident. Meanwhile, Reva and Cassie snuck out of the hospital and headed towards the Royal Council meeting, in hopes of exposing Edmund's role in their accident. Edmund decided to make a preemptive move, though, and abdicated the throne--asking the people of San Cristobel to decide the future of the country in an official election. However, soon Phillip Spaulding overheard that Edmund was planning to fix the election and informed the Lord Chancellor and Col. Dax of Edmund's plans. They agreed to keep a close eye on Edmund. Phillip then informed Richard and Cassie of Edmund's meeting with the Royal Council. Richard went to a news desk and encouraged the people to unite against Edmund. When Edmund saw Richard's appeal to the people on television, he sent Dax to arrest Cassie and Richard. Edmund then decided to lock Richard in the Tower and deport Cassie. Edmund, aware that the people were protesting his actions, declared a state of martial law.

Luckily, Cassie was able to escape with Phillip and Dax's help, Not long after, Phillip was able to sneak into the palace and free Richard. Meanwhile, a suspicious Edmund managed to get Dax's cell phone. He called the last number Dax dialed only to find Richard on the phone! When Edmund and his forces finally located Richard and his supporters, there was a fury of gunfire. Finally, Edmund demanded that the guards go after Cassie. To protect his wife, Richard pulled a gun and shot Edmund. However, unbeknownst to Richard, Edmund was prepared and was wearing a bulletproof vest. While Richard moved off, Cassie became worried and went in search for him only to be caught by Edmund! He then kidnapped her and kept her in the palace's tower, telling no one. He invited his brother to come search the island for Cassie. Over the next few days, Richard, finally, made it to the palace and demanded that Edmund release Cassie. Richard took a knife to Edmund in a desperate plea to get his wife back, but Dax, protecting the crown, stepped between the brothers. Dax produced a knife of his own and, in an effort to protect Edmund, stabbed Richard in the heart and apparently killed him. Shocked, Edmund gave Cassie permission to attend Richard's funeral. She did, and was shocked when Richard opened his eyes--he faked his death! Together, the pair escaped and went public with Edmund's misdeeds.

Exposed, Edmund was forced to leave the island, and Richard was quickly elected as President of San Cristobel. Unfortunately, Richard's tenure as President wound up being a short one thanks to the machinations of Col. Dax. Dax was a strong supporter of the monarchy, and when he learned that the true heir to San Cristobel , William Winslow, had been sold at birth to a fisherman's family, he set a plan in motion to restore the monarchy. Dax manipulated the situation so that Cassie and Richard would adopt a child who he knew to be the son of William, who was now named Alonzo Baptiste. Dax hoped that Alonzo would seek custody of the boy and discover his true identity. Alonzo proved to be an honorable man, however, and decided that his son, Will, should remain with the Winslows. Though Alonzo had every intention of leaving the island, Dax's manipulations forced him to stay and Cassie convinced Richard to offer him a job. Though he wasn't quite sure if Alonzo was trustworthy, Richard would learn that it wasn't Alonzo he had to worry about, but Dax! After learning of Alonzo's true identity and Dax's manipulations, Richard banished Dax from San Cristobel. Though Alonzo had every intention of letting Richard continue to rule, he was forced to accept the crown when Will's mother threatened to take Will away from Cassie and Richard if he didn't take the throne and marry her. Hoping to secure Will's happiness, Alonzo had no choice but to take the throne as San Cristobel's ruler.

Afterwards, Cassie and Richard settled into Springfield life as best they could. While Cassie made plans to refurbish the Jessup farm and buy a hotel, Richard could not bear to let her know he had almost no money, due to the financial dire straits of San Cristobel. When the banks turned him down (thanks to Alan Spaulding) Richard got a job working at a used car lot. He confided his plight to Reva, but swore her to secrecy. In June 2002, Richard and Cassie were at their happiest, and Richard was soon to have more financial independence, after traveling to Chicago for a big car deal. Richard even held out an olive branch to Edmund, which was thrust back in his face. Josh and the Lewis men adopted Richard as one of their own finally gave him the family he had never really had. Sadly, that high point was about to come crashing down. Richard suffered severe injuries after being in a car accident during stormy weather. He quickly fell into a coma, and was in great pain constantly. Only a respirator kept him alive. He woke up once to plead with Reva to take him off the life support. He then suffered a crippling stroke which would leave him as a vegetable. Reva showed him a board worded with yes and no, and when she asked if he still wanted her to euthanize him, he blinked yes. Richard and Reva were closer than they had been in years, and for her former husband, her current friend, Reva ended his suffering.

Richard last appeared in a dream to Cassie, where he made love to her and comforted her. He left behind a rose, and the image of a proud, regal lion, walking into the setting sun. Richard Winslow would be grieved by many, in many different ways, but would never be forgotten. Less than a year after his death, Richard would appear to Cassie again in a dream and tell her to go on with her life.