Will Winslow, born on the island of San Cristobel in 2001, was the child of Camille and Alonzo Baptiste. When Alonzo took off to join the Merchant Marines, Camille discovered she was pregnant. Not wanting a child, she decided to give up it. At the same time, President Richard Winslow and his wife, Cassie, were looking to adopt a baby; by happenstance (or so it seemed) Col. Dax of the former royal military arranged for the Winslows to adopt Camille's child. Dax's motives for far from ultraistic: he had discovered that Alonzo was the true heir to the thrown and wished to restore the island's monarchy. In the meantime, Alonzo had returned and learned about the adoption. It didn't take him long, however, to realize that the child, William, was better off with his adopted parents. Alonzo was all set to leave the island again, but was stopped by Cassie who felt that it was only right for Alonzo to be a part of her adopted son's life and asked him to stay on the island. Soon after, William became deathly ill and Alonzo selflessly donated a part of his liver so that he'd live. Alonzo later went to even greater lengths to secure Will's happiness when Camille reentered his life and informed him that he was the true heir to the San Cristobel throne. When Camille threatened to take Will away from Cassie and Richard unless he married her and took the throne, Alonzo knew he had no choice and for the sake of his son (as well as Cassie's) took the throne in February 2002. He then immediately remarried Camille, only to banish her and Dax from the island. He stayed behind as prince but officially relinquished custody of Will to Cassie and Richard. Immediately after, Richard and Cassie settled in Springfield, the residence of Cassie's family.

Tragically, mere months later, Richard was killed in a car accident. While mourning, Cassie struggled to go on with her life and raise her children, Tammy, RJ, and Will. Finally she found love in the most unlikely of places---her ex brother-in-law, Edmund Winslow. Edmund's ambitions and resentments had caused Richard and Cassie a lot of pain through the years but now it seemed as if he had changed. However, all was not as it seemed and by 2005, Cassie and Edmund were on the outs. Then at Edmund's urging, Alonzo contacted Cassie and requested that Will come to San Cristobel to stay so that he could be groomed to ascend to the throne someday. Cassie was resistant and sought Edmund's help. Edmund tried to convince Cassie that they should all flee Springfield but Cassie was unwilling to hide and traveled to San Cristobel to talk to Alonzo. In the end, she finally allowed Alonzo to have custody of Will so that one day he could rightly claim his heritage. Meanwhile, it was becoming apparent that Edmund had not changed after all and late in the year, after holding Cassie hostage, he was imprisoned in San Cristobel.

In the meantime, being tutored in the palace proved to be a very lonely life for a little boy. With Alonzo busy fulfilling his own obligations as Prince, Will reached out to the one person he thought would understand him—his Uncle Edmund. The pair began as pen pals and finally Will began visiting Edmund, who was now lingering in a state mental facility. Edmund became Will's best friend and his teacher. The Machiavellian prince advised Will on how to get what you want. Finally, in the fall of 2007, Edmund hatched a plan to return to Springfield and used Will to further his ends. At Edmund's request, Will contacted Cassie and told her how lonely he was and asked to come live with her. By this time, the monarchy in San Cristobel was dying and Cassie tried to convince Alonzo to relinquish custody of Will.

When Alonzo refused, the stage was set for a custody battle. Cassie traveled to the island to solicit testimony from Edmund about her parenting skills. While Cassie was at the hospital with Will and Alonzo, there was a sudden power failure and Alonzo was pushed into an electric gate. He was killed instantly and Cassie brought Will home with her. Unfortunately, the transition was not an easy one for Will who was uncomfortable around Cassie and her new husband, Josh Lewis. Making things worse was Cassie's older son, RJ, who made no secret of his displeasure of having Will around. To get back at the sullen RJ, Will locked himself in the barn and then implied that RJ had done it. Several days later, he stole money and then planted it in RJ's back pack. Meanwhile, unbeknownst to everyone, Will was in constant contact with his best friend. At Edmund's suggestion, Will begged his mother to let Edmund visit. Since Will was not connecting to anyone, Cassie complied and Edmund was released from the hospital for a visit.

In December, Will finally began to truly bond with his mother. Around this time, Will was preparing to be in a Christams pageant. However, he was extremely disappointed to be playing a shepherd; he felt as a Prince he deserved a better part. Wanting to be the lead angel, Will discreetly tripped James Spaulding and coveted his part when James was forced to drop out due to a broken wrist. At the same time, Will begged for Edmund to be allowed to attend the pageant. Again against everyone's objections, Cassie agreed. Before the pageant, Cassie and Josh informed Will that afterwards Edmund would be returning to San Cristobel to take over Alonzo's obligations on the island. The day of the pageant, Will met with Edmund on the balcony of the church. There Edmund told Will of his plan to get revenge on Casssie. Will became distressed at the thought of his mother being hurt and warned Edmund not to do it—his father tried to and look what happened to him. The implication being that Will killed his father! Moments later, Edmund came crashing down from the balcony and unbeknownst to everyone Will had two of Edmund's buttons in his hand. Edmund was rushed to Cedars, alive, but left comatose.

Later, Will made a mistake by telling Josh that he was holding Cassie's hand when Edmund fell since Josh distinctly remembered that Will was not there. Days later, a suspicious Josh asked Will point blank if he pushed Edmund. Will became cold and warned Josh to never come between him and his mom. At the same time, Beth showed Cassie some of Will's artwork that showed just how abandoned he felt by Cassie. Back at the farm, Josh continued to press Will about Edmund's fall but when Cassie came home, Will turned on the tears and ran into her arms. Cassie became furious at the allegations Josh was leveling against her son. Days later, Josh tried to bond with Will by bringing him to St. Mark's so they can paint chairs together. When Josh left the room, Will snuck out and ran into his babysitter, Daisy, who was going to ask for more babysitting time so she could buy a new car. Will informed Daisy that he had his own money from San Cristobel and paid her to take him into town so he could buy a Christmas present for his mom, but told her not to tell Josh right away—they could call him later. In town, Will overheard an electrician talking to his wife about needing to work on overtime in order to get extra money. Intrigued, Will offered the man a way to make some extra money. The next day, on Christmas Eve, Josh and RJ went to the mall to do some shopping. By coincidence, so did Josh's ex-wife, and Cassie's sister, Reva. As per Will's plan, the power went out in the mall, trapping all inside and leaving Will alone with his mother. Within a few hours, Josh and RJ made it to St. Mark's prompting a shocked reaction from Will since they weren't supposed to be out so soon. Josh caught on to Will's reaction and accused him of staging the power outage. Will tried to run off, but Josh grabbed him and demanded answers.

In early 2008, Will attempted to frame Reva for Edmund's fall by planting the button in Reva's purse. Afterwards, he used a voice distortion toy to call the police and report Reva for "something suspicious". When Reva was brought in for questioning regarding Edmund, Josh accused Will of setting her up. Again, Josh's accusations upset Cassie and Will played into her sympathy by packing his things and telling his mother that he wanted to leave before Josh sent him away. Soon after, Josh and Reva got Daisy to ask Will to meet her at St. Mark's. When Will arrived, he was met by Josh and Reva. Though Will tried to run, the pair stopped him and got him to confess to shoving Edmund. Will, later, informed Detective AC Mallet that he shoved Edmund because he was threatening to harm his mother. Will made the entire incident sound like a tragic accident. Later, when Cassie told Will how proud she was of him telling the truth he finally confessed that it was no accident. He wanted Edmund gone. That same day, Jeffrey scanned through the security tape from San Cristobel and discovered that Will intentionally pushed his father into that electrical gate. As Jeffrey relayed this to Josh, Cassie spirited Will away to the Bauer cabin and informed him that they were going to stay there until he learned that violence was not the answer. Later, Jeffrey and Josh located Cassie and told her about Alonzo, but she protested when Jeffrey tried to take Will into custody. Cassie convinced Jeffrey to let Will stay at the cabin with her and Josh for a night. However, since Tammy's memorial service was coming up, Jeffrey must have taken pity on Cassie and let Will stay with her longer. Jeffrey was able to get Will into Fairmont but Cassie resisted and proclaimed that she promised Tammy she would not send Will away again. Apparently out of respect for Cassie, Jeffrey did not fight her. Unfortunately Cassie's attempts to correct Will using kindness and love were not working.

Meanwhile, Will, who had tried to kill RJ by covering up a sign that warned of thin ice, tried again to cause RJ's demise while they were outside playing by the railroad tracks. Will purposely threw the ball onto the tracks and RJ was forced to go after it. RJ's foot became stuck while a train was approaching. Though RJ yelled at Will to help, Will stood by and did nothing. Fortunately for RJ, Cassie arrived and saved him though she kept the incident from Josh. Not long after, Will was thrown out of school because it was feared he was a danger to other children.

Josh and Cassie continued to be at odds about whether Will should be at home or not. Afterwards, Cassie seemed ready to admit that Will needed more help than she could provide and prepared to send him away. After finally arriving at the school, Will ran away and went to Reva's cabin. Will entered the empty cabin and began trashing the place. At the same time, Cassie stopped by and watched helplessly as Will trashed the cabin. Jeffrey informed Cassie that they were going to have to press criminal charges against her son. Afterwards, Will was sent away to juvenile hall. However, Cassie was determined to stay by her son and convinced a guard to allow her to have some unauthorized visits. In the meantime, Will snatched a guard's taser gun. That same day, he was visited by Jeffrey and attempted to shock him with the taser by Jeffrey stopped him. Later, Cassie convinced a judge that Will was merely a little boy who felt abandoned by his mother and needed love. The judge sympathized and the charges against Will were dropped. Though Will was supposed to be sent back home, due to Josh's work commitments, it was decided that he would stay at Reva's. A few days later, Will accompanied RJ, Josh and Cassie for a game of baseball. At one point, Will menacingly started to hit RJ over the head with his baseball bat but was stopped by Josh. Later, Josh confronted Will about what he'd almost done and tried to tell him that by hurting RJ he would hurt Cassie as well. Will ran to Cassie's room to get away from Josh and Josh instructed him to stay there. Later, Cassie lovingly comforted Will who told her that he was tired. When he asked where Josh was, Cassie informed him that he was at Reva's.

Will snuck out and went to Reva's where he decided to get rid of his stepfather once and for all by sabotaging a gas valve—hence causing a carbon monoxide leak. Later, Will went home and matter-of-factly told Cassie that Josh was dead. When Cassie informed him that she just spoke to him, Will didn't believe her and calmly insisted that he was dead. When Cassie asked Will why he'd say that, Will told her exactly what he'd done. Unnerved, Cassie told Will to pack and then attempted to flee town with him. Though she hired a man to help her get Will out of town, when Cassie was discovered by Josh and Mallet, she finally realized that she couldn't protect Will forever and turned him in to the police. Though Will was devastated, the moment quickly past when he was asked if he wanted Mallet to turn his siren on and he willingly went off into police custody.