Jamal Woods was street smart -- but also a bit of a troublemaker. His mother died when he was just fourteen. He doesn't have much other family except for his cousin, Dara Jensen, who also lives in Port Charles. While living on the streets, Jamal was drawn into a life of crime. On his way into town, he made sure Scott and Lucy would hit his bike with their car. Jamal wanted a "deal" from Scott, but Scott knew that he was being conned. Jamal befriended Alison Barrington, and they teamed up to help Jamal's pregnant friend Val escape from thug Cedric. Alison went snooping and killed Cedric in self defense, but had no memory of it, so Jamal took the rap, he was granted bail but it was revoked when the authorities believed he was the mastermind behind the numbers operation, not Cedric. Alison helped Jamal evade the police and hide at the Barrington cabin. Their friendship began to turn into more, and this was the start of a serious relationship. They were shocked when the police believed Jamal kidnapped Alison. Jamal was cleared of the charges. Alison stood up to Amanda and refused to stop seeing Jamal. Jamal distanced himself and admitted that he took a deal with Amanda to stay away from her. Amanda told Alison that she could continue seeing Jamal but would be disinherited. Alison surprised Jamal when she moved in with him. She proclaimed her love for him and Jamal realized how much he loved her.

Strapped for cash, Alison convinced Jamal to open up a bike shop. Their happiness was threatened when Jamal's biker buddies showed up at the shop trying to convince him to race again. Alison and Jack were given $25,000 which Alison thought came from Amanda (who suffered a heart attack, leading to them making up). It was really from Jamal's foe, Zach. Zach used the cash as a way for Jamal to be indebted to him. Jamal agreed to race if Zach backed off. Jamal raced for the last time, but Zach again forced Jamal to race. Alison prevented Jamal from racing by throwing his keys away. Zach forced Jack to race for Jamal by holding Livvie captive. Jack was killed after he threw the diamonds he was smuggling out of the bike. Jamal arrived too late to stop it. Jamal, Alison and Livvie covered up Jack's body and lied to everyone that Jack stole cash from the bikeshop and bolted town out of disgrace. Jamal decided to confess to the cops, despite Alison's pleas he not. Jamal and Alison were shocked when they overheard an officer tell Garcia that Zach Vernon was dead. They feared Livvie killed him.

Jamal and Alison would learn that Livvie didn't kill Zach (Caleb did). After Jack shockingly returned from the dead, the group eventually learned that he was now a vampire, and had been turned by a brooding vampire named Caleb who was fascinated by Livvie. While they fought Caleb's growing influence over Livvie, Jamal stole blood from the hospital blood bank to feed Jack, and stopped Jack from killing himself. This began the tight bond between the two men that continued long after Jack was freed of Caleb. Also at this time, Nurse Gabriela Garza, Caleb's thrall, interfered with Jamal's efforts, but couldn't bite him. Jamal found out that vampires can't bite blood relatives, and after more digging, learned that he was her brother. After a rocky start, they became very close.

Caleb was vanquished, and Jamal and Alison were closer than ever. Unbeknownst to them, Caleb was dormant, not dead, and began using Livvie to split the town apart. Jamal's old friend Valerie returned to town, which led to Alison finding out that Jamal and Alison had been more than friends for one night, meaning baby Hope might be Jamal's. Hope's adoptive parents said he couldn't be, but this was soon uncovered as a lie. Alison was threatened by Valerie and Jamal's past and went to visit the Hartmans. They revoked Valerie's visitation rights, and both Valerie and Jamal were furious with Alison when they learned of what she had done.

Hope needed a kidney transplant, which Gabi provided. Jamal realized his daughter had a good home, and signed over his parental rights. Valerie decided to get even, then decided to win Jamal for herself. She hounded him for weeks, even moving in with him and Alison, then attempting suicide, all of which pushed Ali into friend Rafe's arms.

In January 2002, Valerie escaped the psych ward and held Alison at gunpoint. Jamal ran in front of her, causing a struggle which led to Valerie's death. Jamal really blamed himself, but took his rage out on Alison, telling her that none of it would have happened if she didn't get involved. They separated, and although Alison was devastated, she found herself being comforted by Rafe Kovich. By the time Jamal realized what he'd given up, Alison was happy with Rafe, and had decided she wanted to stay with him.

Jamal went into a downward spiral, getting into fights, gambling. Gabi was injured when she stepped in the middle of a fight between him and her brother (his brother by association), Ricky. She recovered and left town, but not before pleading with Jamal to heal himself. Jack was equally concerned, and never got off Jamal's back. After a fistfight with Ricky, Jamal began to come to his senses, but his past cheating with gambling caused him to be kidnapped by thugs. Jamal called Ricky, who was also captured. Only the intervention of Ricky's girlfriend Casey saved their lives.

After Alison is accused of killing Kevin Collins, Jamal and Jack are constantly at her side, defending her, and it is the smarts of these 3 combined that clear Alison's name. Tragically, the stress of the trial causes Alison to have an aneurysm and Jamal and Jack and the rest of her friends remain at her side. It is only the kiss of the returned Rafe that brings her out of her coma. It is then that Jamal realizes that maybe Rafe and Ali really are meant to be.

Slowly, Jamal tries to move on with his life and Jack does the same, now that Livvie has gone completely out of her own nature. She convinced Rafe, who lost all memories of his life before on earth with Ali, that he is in love with her. With the presence of the Avatar in Port Charles, a new face is seen in town. Marissa Leong is a reporter very interested in the strange happenings in Port Charles. Much to Ricky's surprise, the face is identical to his lost love, Casey, but it turns out she is actually her unknowing twin sister. She believed that Casey died at birth and everyone, including Jamal can't get over their shared resemblance. Marissa begins to spend more time with Jamal as she searches for facts on the mysterious Avatar.