International businessman Damian Grimaldi came to Oakdale with his wife, Lily Walsh Grimaldi. Damian and Lily had met in Italy, immediately hit it off and married soon after. In Europe, they had a fairy tale marriage, however the return to Oakdale would change things dramatically. Upon their arrival in Oakdale, Damian immediately sensed that his wife still had feelings for her ex-husband, Holden Snyder. Over the course of several months Damian's jealousy became so great that he turned to boxing to relieve his frustrations. Horrified at her husband's new hobby, and also skeptical of his business dealings, Lily ran right into Holden's arms. Although Damian didn't know about this, he soon found out when Lily was kidnapped and held for ransom. Desperate to save his wife, Damian paid the ransom and confronted the kidnapper who revealed Lily's affair. Enraged, Damian attacked the kidnapper only to get shot in the process. Luckily, the police apprehended the kidnapper. Unnerved by how her actions hurt Damian, and touched by how he tried to save her, Lily tried to give the marriage another try. Lily became pregnant and had a son named Luciano (Luke). Again, Damian's shady business dealings unnerved Lily and she tried to get a legal separation. Not willing to let her go, Damian had her drugged and spirited her and their son to his childhood home in Malta.

In was in Malta where Damian would receive the shock of his life. Conspiring with his mother, Orlena, to keep Lily in Malta, Damian had no idea how demented his mother was. After weeks of keeping Lily's family away, Damian learned a horrifying fact: his mother wasn't who he thought she was. The truth was that Orlena was not his mother at all, but his childhood nanny. Orlena, jealous of Damian's mother, drugged her the same way she was drugging Lily and then usurped her life. By the time Damian learned of this, Orlena had committed suicide while his real mother left brain damaged from over 30 years of medication. Sickened by what his parents had done, Damian resolved to turn over a new leaf and he and Lily resumed their marriage. Unfortunately, Damian perished in a plane crash soon after.

Or so everyone thought. Lily was shocked, a year later, when Damian suddenly arrived at her door. Damian explained to Lily that he survived the plane crash and was cared for in a monastery in Maryland. Of course by this time, Lily had moved on with her life and was involved with Holden again. Though hurt at first and determined to win back his wife and son, Damian finally realized that Lily loved Holden and so he let her go and left Oakdale to become a monk.

Years later, Damian showed up on Lily's doorstep again claiming to want to teach a young Luke about his heritage by taking him to Malta. After telling Lily that he never became a monk but returned to the family business, Damian asked Lily if he could spend time with their son, Luke. Wary of Damian's motives, Lily refused. When Lily learned that Damian had planned to take Luke away, Damian was forced to tell her that Luke's life was in danger. Apparently, Damian's efforts to clean up business dealings at Kinsley-Malta ruffled some feathers and people threatened him and his family. When Lily still refused Damian's request, he decided to take things into his own hands by kidnapping Luke. Scared for Luke's safety, Damian then arranged to fake their deaths and leave Oakdale. Unfortunately, Holden caught up with them and all three got caught up in the explosion. Unbeknownst to anyone, all three escaped to Malta only to have Holden and Luke captured by Damian's half-brother, Dante, who wanted the Grimaldi Empire to himself. Lily though refused to believe that Luke and Holden were dead and eventually made her way to Malta only to be captured herself! With Lily's life on the line, Damian confronted his selfish half-brother, but was nearly killed until Lucinda showed up and killed Dante. Still worried about Luke's safety, Damian spirited him away again. After making a last ditch effort to ensure Luke's safety by faking his death, Damian told his son that if the plan failed, they'd be forced to disappear forever. What Damian didn't count on was Luke's rebelling against him and refusing to be separated from his family forever. Deciding that he'd gone too far, since Luke wouldn't blindly follow him simply because they were father and son, Damian told Luke to never reveal that he is a Grimaldi and he left Luke alone in the church so he could be reunited with Lily and Holden.

Years later, Damian showed up at Lily's asking to see the now-teenaged Luke. Damian informed her that his situation had been fixed and no one was out to get him or his family any longer. When Lily told him she didn't think it'd be a good idea for him to see Luke, Damian gave her a Grimaldi heirloom to give to Luke to pass on to his son. At that, Lily burst into tears. At this point, Luke came home and, upon seeing Damian, asked Lily if she called in the big guns to "fix him." Lily denied it and Luke announced that he wanted no part of his father. When Damian asked why Luke seemed so sad, Lily admitted that their son "thinks he's gay." As Damian wondered if maybe Lily and Holden's parenting drove Luke to question his sexuality, he offered to help Lily with her problem. Damian suggested that Luke go to a special camp where therapists could deduce whether Luke was actually gay or just confused .Though wary, Lily agreed. Unbeknownst to her, the goal of the camp was to "reprogram" gay men to become straight. Hoping to get on Luke's good side, Damian told the doctor in charge of the camp, Kreeger, to tell Luke that it was Lily's idea. Later, Lily discovered the truth about the camp while Luke realized what kind of camp he'd be going to. The two had an argument which ended in Luke accidentally shoving a pregnant Lily down the stairs. Lily lapsed in a coma and Damian ordered Kreeger to not reveal that he was the one who wanted Luke to go away.

Seeing tension between Holden and Luke, Damian quickly took advantage and fed on Luke's belief that Holden blamed him for Lily's condition. Suggesting that Luke move in with him at Fairwinds, Damian kept the teen isolated from Holden by insinuating that Holden was still angry at him and made him so Luke would avoid him. Although it worked for several weeks, once a still comatose Lily gave birth to a son, Luke decided he had to patch things up with Holden. Desperate to get Luke to stay with him, Damian "accidentally" dropped a bottle of pills in front of Luke. Luke took the bait and asked his cousin Lucy what they were. Upon learning the medicine was for terminally ill patients, Luke confronted Damian who confessed he was dying. Not wanting to abandon Damian, Luke made plans to go back to Malta with him until the end. Despite Damian's pleas to keep his condition a secret, Luke told Holden who immediately suspected Damian was lying. To prove it, he recruited Lucy, who was a doctor and already formed a friendship with Damian. To get in Damian's good graces, Lucy staged a fight with Lucinda and announced she was moving out. Taking pity on this sweet young woman, Damian invited her to stay at Fairwinds with him and Luke. At this point, a man named Sergio came into the picture and warned Damian that Lucy could be a threat to getting Luke out of the country as soon as possible. Damian disagreed and decided to trust her. That trust disappeared though when Damian spotted her drugging his tea. Damian quickly got the upper hand by switching the glasses.

With Lucy drugged, he locked her in the wine cellar and then quickly got Luke to the airport. Unfortunately, Holden and the police met them there. The situation got out of hand with Sergio taking Luke hostage but luckily Damian was able to diffuse the situation. His plan foiled, Damian was forced to confess that the reason he came to Oakdale was to get Luke to turn over his inheritance to him so he could pay off some dangerous men. During the course of Damian's revelation, Luke figured out it was Damian, not Lily, who wanted to send to a deprogramming camp. Angry that Damian had been playing him for weeks, Luke bitterly disowned his father and, although he was within rights to pursue kidnapping charges, he declined in order to spare his family—the Snyders.

A few years later, Damian returned to town just in time to save Luke's life when Luke was struck by a speeding car. Damian assured an angry Luke that he was there to make amends. Damian assured a skeptical Luke that he accepted Luke's sexuality and accepted Noah's role in Luke's life. Though Luke had doubts, Noah was convinced of Damian's sincerity. While Holden didn't trust Damian at all, Lily came to trust Damian more and more and did her best to help Luke and Noah, even though Holden and Luke didn't approve of her professional involvement with Damian. Eventually, Zach and Zoe (who turned out to really be lovers), kidnapped first Noah and then Luke. Zoe, apparently an illegitimate heir to the Grimaldi fortune, felt entitled to Luke's money. In the end, Lily proved to be correct about Damian when he saved Luke and Noah from Zach and Zoe.

Later, Damian formed a friendship with Holden's newly divorced sister, Meg. Despite her family's warnings, Meg was captivated by the charming Damian. Unfortunately, it was obvious that Damian still had feelings for Lily. Those feelings appeared to be mutual when Lily became jealous of Damian's relationship with Meg. It wasn't long before Damian and Lily shared a smoldering kiss. Not long after, the Snyder family was shocked when Holden's truck went off a cliff. Though the body could not be identified, the consensus seemed to be that Holden was dead. Damian wasted no time comforting Lily. In record time, Damian and Lily embarked on an affair. Meanwhile, Damian discovered that there was no DNA evidence that proved that Holden's body was the one on the scene—a revelation that Damian kept to himself. Soon, Damian convinced Lily to marry him. That same day, a very much alive Holden returned. Incensed that Lily married so soon after his supposed death, Holden decided to annul his marriage to Lily so that she could stay with Damian.

Angry that she'd been tossed aside, Meg had started looking for dirt on Damian. Meg discovered that Damian knew that there was no DNA proof that the dead body found earlier was Holden's. Obsessed with Damian, Meg used this information to blackmail Damian into dumping Lily and staying with her. Damian seemed to comply by making love to Meg. Afterwards, when Lily caught a half dressed Meg with Damian, Damian accused Meg of being delusional. To make Meg look even more delusional, Damian laced the cake for his and Lily's vow renewal ceremony with a toxin and planted the toxin in Meg's purse. Meg revealed the truth about Damian, but with the toxin in Meg's possession, Lily accused Meg of concocting the story to cover up Meg's own crime: trying to kill Damian and Lily. Irate, Meg threatened Lily with a glass shard—which led her to being committed to a psychiatric hospital.

Meanwhile, Holden and Molly Conlan began investigating Meg's story that Damian had covered up the fact that the body found was not Holden's. Molly got Officer Grady to admit that Damian had blackmailed him; however, Damian warned her that her newfound information would only serve to reunite Holden and Lily, and Molly kept quiet about what she'd learned. However, Molly couldn't stay quiet for long and confessed the truth to Holden. Meanwhile, Meg crashed Damian and Lily's vacation, and as Meg and Damian fought over a syringe, Damian inadvertently choked Meg with her scarf. Thinking Meg was dead, Damian dumped her body in a trunk. Unfortunately, Lily found her and when Holden showed up, Lily told him everything. A revived Meg popped out of the trunk, and Damian fled. Luke informed Holden that Damian went on the run, and Holden confronted Damian at the docks. After a brawl with Holden, Damian disappeared and was presumed dead when a body matching his description washed up on the shore.

Though Holden was booked for murder, unbeknownst to everyone, Damian was alive. When, thanks to Molly, the Maltese government backed down on seeking extradition for Holden, Damian returned to Oakdale in secret and manipulated Faith to destroy the Snyder family. Faith tried to trick Lily into unwittingly meeting Damian, but under Lily's interrogation, Faith revealed that Damian was alive. Molly informed Holden that Damian had checked Faith out of her school. Holden escaped police custody, and Molly and he arrived at Damian's rendezvous spot to find Damian tying up Faith. Damian knocked Holden out and absconded to a warehouse with Lily. Though Damian tried to convince Lily that they belonged together, she was appalled at what he'd done and said that she was an obsession with him. Undeterred, Damian warned her that she'd change her mind after being alone with him at sea. At that point, Molly trailed them, and Holden arrived after Damian had locked Molly in a closet. Following an intense confrontation, police hauled Damian off to jail. At the police station, Luke finally denounced Damian and the Grimaldi name.