Stole chips and embezzled money from Las Vegas casinos [before 2000]
Blackmailed the Forresters [2000-2001]
Forced the Forresters to listen via telephone as he deflowered Bridget Forrester 
Punched Whip Jones 
Had an affair with Jackie Marone and drugged her to taunt her catatonic husband, Massimo Marone 
Kidnapped Amber Moore and did time as an accessory to the murder of Ray Elkins 
Arrested for kidnapping Nikki Newman 
Served time for stealing evidence and obstructing justice in the death of Diane Jenkins 
Deacon Sharpe was brought to Los Angeles by Rick Forrester, whose ex-wife, Amber Moore, was set to marry longtime friend C.J. Garrison. Rick and Amber had been raising Eric Forrester III, a child Deacon fathered with Amber's deceased cousin, Becky Moore; Rick paid Deacon $100,000 in exchange for full custody of Little Eric, hoping it would convince Amber to come back to him. But the slimy Deacon saw that both Rick's family, the Forresters, and C.J.'s family, the Spectras, wanted Little Eric, so Deacon held out and sparked a bidding war between the rich fashion dynasties. In the meantime, Deacon's girlfriend, Carmen Arena, was angry that Little Eric was living with them and jealous of Deacon's growing attraction to Amber, so Carmen threatened to throw the baby off the roof of their apartment building. Deacon and Amber rescued Little Eric, but in the struggle, Carmen fell to her death.
Deacon had been raised by the abusive Daryl, who again beat his son when he came for a visit. Deacon swore to be a better father to Little Eric, and persuaded Amber, who had broken up with C.J., to live with him for four months, after which Deacon promised he would sign over his parental rights to Amber. Although Amber began to bond with the very much in love Deacon, she still had feelings for Rick, and accepted Rick's proposal of marriage. Hurt by Amber's rejection, and angry with the Forresters for demanding that he stay away from her, Deacon took full advantage when he met Rick's sister, the virginal Bridget Forrester. Deacon crashed Amber's wedding and told the Forresters that if he couldn't have Amber, he would take Bridget; her father, Eric Forrester, and her brothers, Ridge and Thorne Forrester, responded by beating Deacon up and throwing him out.
But Deacon turned the tables on the Forresters by whisking the smitten Bridget off to Las Vegas to get married. When the Forresters called demanding that Deacon let Bridget come home, Deacon put the telephone's earpiece in a glass of water and forced Bridget's family to listen in as he deflowered her. Furious, Eric hit Deacon with his car, which only made Bridget more devoted -- until she heard Deacon tell Amber that their marriage was a sham: Deacon really wanted to raise Little Eric (now called "Little D") with Amber. Deacon realized he really did have feelings for Bridget after she ran off and got into a car accident, and agreed to a real marriage with her.
Bridget's mother, Brooke Logan, begged Deacon to divorce Bridget; Deacon gave in, knowing his lingering feelings for Amber were unfair to his wife. But Brooke and Deacon's emotionally charged conversation led to lovemaking. Deacon was surprised when Bridget responded to his admission of infidelity by giving him another chance, and more so when Brooke gave Deacon a job as the head of Forrester Creations' public relations department. However, Brooke soon took an extended leave from Forrester; Deacon tracked Brooke to a spa, where she admitted she was carrying his child. Deacon and Brooke continued their affair behind Bridget's back, but when Brooke's longtime nemesis, Stephanie Forrester, exposed Brooke's baby bump at a press conference, Forrester employee Whip Jones took responsibility to save her reputation. Deacon enjoyed taunting Whip and sleeping with Brooke on the sly, but ultimately, Brooke became Whip's husband.
Stephanie overheard Deacon and Brooke talking about their affair and demanded that Deacon leave Forrester for Bridget's sake. Believing her mother was carrying Whip's child, Bridget attended Brooke's baby shower; Brooke received a baby monitor, over which Bridget heard how her husband had impregnated her mother. Deacon was stunned when Bridget later revealed that she had helped deliver his love child, Hope, and understood when Bridget threw him out and burned his clothes. Deacon agreed with Brooke that Hope's paternity should remain secret, so Deacon left town for a while to keep the truth from being exposed. A few months later, however, a darker Deacon returned, incensed that Brooke was reuniting with her on-again-off-again love, Ridge Forrester; Deacon didn't want Ridge raising Hope.
Deacon blackmailed Brooke into financially supporting him by threatening to expose their affair to Ridge and the Forresters, eventually following Brooke to Portofino, Italy, where Forrester Creations was holding an important fashion show. Ridge punched Deacon when he found him with Brooke, while Eric, who had learned of the affair, convinced Deacon to put some distance between himself and Brooke. But Ridge's biological father, Massimo Marone, didn't want Ridge back with Brooke and talked Deacon into confronting Ridge. Deacon was disappointed when Ridge left Brooke, who wasn't interested in resuming her relationship with Deacon.
An ex-boyfriend of Amber's exploited her newfound fame as a Forrester and released a private videotape of their lovemaking, but Amber's twin sister, April Knight, came forward and claimed she was its star. April wanted to be a rock singer, so Deacon decided to become her manager and helped kick off April's career. For the sake of his baby daughter, Deacon also gave up drinking and joined Alcoholics Anonymous, where he met Macy Alexander. Macy had been presumed dead and wanted to get her own singing career back on track, so Deacon offered his assistance, while Macy encouraged Deacon to pursue his rights regarding his children, Little D and Hope. Deacon and Macy fell in love, but, the night of her big comeback at a club owned by Oscar Marone, gangsters that Oscar owed money to rigged a chandelier to fall on Macy, who lapsed into a coma and was taken off life support off-screen.
Deacon hoped to reunite with Bridget and start a fashion house with her, but when Eric found out, he confronted Deacon; the men struggled over a gun, and Deacon was shot. After he nearly lost the use of his legs, Deacon told Eric he would clear him of all charges connected to the shooting if Eric would make Deacon's new fashion house a subsidiary of Forrester. While digging up dirt on Eric on Massimo's behalf, Deacon became enamored of Massimo's wife, Jackie Marone. Meanwhile, Brooke was set to marry Jackie's son, Nick Marone; Nick asked Deacon if he could adopt Hope, adding that, in exchange, Deacon could see his daughter whenever he wanted. Deacon agreed to Nick's proposal.
The powerful Massimo suspected his wife of cheating and threatened Deacon; after coming to believe in Deacon's innocence, Massimo hired him to learn the identity of the interloper. But it was Deacon himself who was planning a future with Jackie, and, when Massimo found out, he had a stroke that appeared to leave him catatonic. Deacon taunted Massimo, flaunting his affair with Jackie and even drugging her in front of him -- but, though Massimo couldn't move or speak, he was aware of his surroundings and vowed revenge on Deacon. Eventually, Massimo confronted Deacon and Jackie with a gun, but Deacon and Jackie had fallen in love, and she asked for a separation, the condition of which was to install Deacon as vice president of her new fashion house, Jackie M.
Massimo learned that Deacon was a recovering alcoholic, and arranged for Deacon to be tempted so he'd fall off the wagon. Deacon indeed began drinking again, and tried to fight his addiction for Jackie's sake, but when the struggle became too much, he pushed Jackie out of his life and left Los Angeles, checking himself into rehab.
Amber had since moved to Genoa City, Wisconsin, and was involved with Daniel Romalotti, an artist. Daniel had been asked to forge a painting on behalf of the FBI, but it was really a ruse by Deacon, who wanted to have Daniel imprisoned so he could have Amber for himself. Deacon told Amber he would make sure Daniel was freed if she slept with him, but after she did, Daniel wanted nothing to do with her. Amber didn't know that Deacon, who was passing himself off as an art entrepreneur, was in town looking for a valuable painting that had been in the possession of Ray Elkins, the one-time cellmate of child abuser Tom Fisher. Deacon was working with Tom's son, Ryder Fisher, to find the artwork; when Elkins was violent toward Ryder the way Tom had been, Ryder killed him. During his search for the painting, Deacon also dallied with art expert Victoria Newman, who slept with Deacon after a fight with her husband.
Daniel became a suspect in the murder of Elkins; Deacon kidnapped Amber and told her he had evidence that would clear Daniel of the charges, which he would turn over if she married him. Amber agreed, but Daniel found out about Ryder's involvement in Elkins' death, and stopped Deacon from marrying Amber by offering to help find the painting. With assistance from his friends, Daniel located the artwork but returned it to the museum from which it was stolen, and Deacon was jailed for kidnapping Amber and being an accessory to the murder of Elkins. Deacon told Amber that his son, Little D, was living with Amber's mother, Tawny Moore, in Furnace Creek, California -- but not that Deacon had been put up to the whole attempted art heist by Ryder's aunt, Sarah, the supposed sister of nefarious villain Sheila Carter, who had threatened Little D's safety if Deacon didn't go along with her.
After serving his sentence, Deacon planned to return to California, but met Daniel's mother, Phyllis Summers. Phyllis wanted to make her on-again-off-again love, Nick Newman, jealous, so she kissed Deacon, who had taken a job as a bartender at Genoa City's new bar, Gloworm. Deacon noticed that Nick's mother, Nikki Newman, whom he had met in Alcoholics Anonymous, was a frequent customer and encouraged her to become sober again. However, Meggie McClain wanted Nikki's longtime paramour, the very rich Victor Newman, for herself, and was spiking Nikki's non-alcoholic drinks in an attempt to push her off the wagon. In exchange for a large sum of money, Deacon agreed to help Meggie in her quest to secure Victor and became Nikki's "drinking buddy," even though he wasn't actually drinking himself.
After Meggie arranged for Victor to find Nikki passed out in Deacon's bed, Victor sent Nikki to rehab, but Meggie made sure Deacon was admitted there, too. Victor confronted Deacon and raged at Nikki for turning to Deacon, after which Deacon realized he had developed real feelings for Nikki. Deacon told Meggie he didn't want to be part of their con anymore, but Meggie drugged Victor, her plan being to marry him, then murder him and inherit his wealth. Victor turned the tables on Meggie, and she was promptly arrested, yet all Nikki had been told was that Victor was marrying another woman, so Nikki found comfort in bed with Deacon. Victor caught them together, told them the marriage was a ruse to entrap Meggie, and turned his back on Nikki.
Deacon and Nikki grew closer, but Meggie called Deacon from jail and threatened to tell Nikki he was part of her scheme if he didn't get her out of jail. Deacon brought Meggie clothes for an escape, but secretly tipped off a prison guard so that she would be caught before she could break free. Meggie summoned Nikki to her cell and told her that Deacon had been involved in her plot; Deacon couldn't convince Nikki that he had actually fallen in love with her in the process. But, after Victor moved on with Diane Jenkins, Nikki began drinking heavily, and Deacon implored Victor, Nick, and Victoria to help Nikki. Victor soon took Nikki out of town and admitted her into another rehab.
Before long, Diane's body was found in a local park, her head having been bludgeoned. Deacon had seen many Genoa City residents arguing with Diane just before the murder, but the police spotted Deacon at the crime scene the next day. Nikki returned from rehab but was still drinking, and had woken up bloodied next to Diane's body. Deacon admitted that he had witnessed Victoria killing Diane, pointing out that Nikki had been trying to save her, and told Nikki that he wouldn't report Victoria to the cops if she would marry him. Deacon took the drunken Nikki to Las Vegas for the ceremony, then leaked the nuptials to the tabloids. Nikki's billionaire best friend, Katherine Chancellor, offered Deacon a fortune to annul the marriage, and Nick attacked Deacon for taking advantage of his mother. Meanwhile, Nikki was stunned when Victoria insisted she hadn't killed Diane, contrary to Deacon's story.
After Nikki told Victor that she had killed Diane, Victor confessed to protect Nikki and was sent to jail, but, when Victor was about to be handed a 25-year sentence, Nikki barged into the courtroom, admitting her guilt, and was jailed for contempt. Deacon visited Nikki in prison, where she railed at him for coercing her into marriage; he quit his job and went on a spending spree using her money. But soon, Deacon revealed that he really cared for Nikki, who cozied up to him in an attempt to find out more about Diane's murder. Deacon spied Nikki looking through files on his laptop and was about to strangle her before they were interrupted; Nikki had been watching a video of Deacon having sex with Diane.
When Nikki caught Deacon hiding Super 8 film on which the sex video had been shot, he kidnapped her and took her to a warehouse to show her other videos: he had footage of Nikki hitting Diane in the head with a rock. But the footage also revealed that Diane was trying to inject Nikki with a syringe -- Nikki had acted in self-defense, and Deacon was only trying to protect her. Deacon was arrested for kidnapping, but the video helped exonerate Victor. Questioned by the district attorney, Deacon confessed that Diane had come to him for help: she had run afoul of Victor and wanted to frame him for her "murder," after which she would leave the country alive and well; Deacon was to film the faked killing. But then, a very drunk Nikki had stumbled into the park and fended off Diane's attack with the rock, so Deacon further bludgeoned Diane to make it look like someone bigger and stronger had killed her. Deacon had taken the park's security camera, and other items, to keep anyone from finding out about Nikki's involvement. In addition to serving time for kidnapping, Deacon now faced seven years in prison for obstructing justice.
Deacon helped clear everyone else of charges when he recognized a woman who had helped him clean up after Diane's murder: the notoriously insane Patty Williams, who had actually killed Diane for trying to seduce Jack Abbott, the object of Pattys' decades-long obsession.
While Deacon served out his sentence, he was visited by Los Angeles-based publishing magnate Bill Spencer. Bill objected to his son, Liam Spencer, marrying Deacon's daughter, Hope Logan, and promised to pull strings to get Deacon out of jail if Deacon would go to Italy and stop the ceremony. Deacon, who had undergone beatings in jail and desperately wanted to see his daughter, agreed, and Bill blackmailed the prison's warden into setting Deacon free. As per his arrangement with Bill, Deacon showed up at his estranged daughter's hotel room the day of her wedding; while Hope was shocked to see her long-absent biological father (she had been raised by Nick Marone and Ridge Forrester), she forgave him for not being there for her. Deacon was so moved by his daughter's compassion that he almost couldn't go through with Bill's orders, but he forced himself to steal Hope's cell phone and forge a note telling Liam she'd changed her mind about marrying him.
While Bill and Deacon's interference nearly did split Hope and Liam up, the young couple reunited; Bill paid Deacon off anyway and told him never to return to Los Angeles. Deacon texted Brooke, wanting to see Hope; Brooke kept the text a secret, which caused Ridge to leave Brooke during their honeymoon. Undeterred, Deacon confronted Bill in his office and said that if Bill didn't give him a job, he would tell everyone how Bill used him to stop Hope's wedding. Bill threatened to have Deacon killed if he didn't leave town, but Bill's pregnant wife, Katie Logan, walked in during this exchange; the news of Bill's illegal activities regarding Deacon caused Katie to go into premature labor and nearly die because of the strain on her transplanted heart.
After nearly two years, Deacon resurfaced in Los Angeles and met Quinn Fuller in a bar. Hope had been torn between Quinn's son, Wyatt Fuller, and Liam; when Quinn learned Deacon was Hope's father, she offered him a place to stay if he would help push Hope toward Wyatt. Deacon visited Hope, who forgave him for what happened in Italy and agreed to foster a father-daughter relationship with him. Deacon then introduced himself to Wyatt and bonded with him over a bottle of Scotch.
Deacon thought Quinn was kidding when she said she wanted to kill Liam, but Deacon told Wyatt about a sword Quinn was making, allowing Wyatt to prevent Liam's murder. While Quinn was reportedly away at a psychiatric hospital, Deacon spent time with Brooke, who had nearly married Bill in Abu Dhabi; Ridge had stopped the wedding but suffered brain damage after falling out of Bill's helicopter into the Persian Gulf. Following Ridge's hunch that Bill was responsible, Deacon helped Katie find evidence of that fact. While Brooke reexamined her relationship with Bill, Deacon asked Brooke for another chance and kissed her.
Deacon learned that Ricardo Montemayor, the man who bequeathed a priceless blue diamond to Wyatt, had been murdered. Deacon found a video Ricardo made for Wyatt that hinted at Quinn's involvement; when Deacon confronted Quinn, she claimed innocence but held Deacon at gunpoint. Deacon and Quinn worked to keep Brooke and Bill apart, and Deacon bonded with Brooke over their daughter, Hope. Just as Deacon proposed to Brooke, Bill interrupted with his own proposal, but Brooke rejected both men and moved to Milan to get herself together. Deacon fell into bed with Quinn, who wasn't looking for any kind of commitment, so the two enjoyed a casual, flirtatious relationship.
Deacon was ready to give Quinn up when Hope refused to accept them as a couple, but he allowed himself to be seduced back into Quinn's bed. Later, seeing how Quinn was fixating on Hope, who was expecting a baby with Wyatt, Deacon asked Quinn to respect Hope's request for privacy. Though Deacon was devastated when Hope fell down a flight of stairs and miscarried after arguing with Quinn, Deacon talked Quinn out of jumping off a building and stood by her.
Deacon became concerned for Brooke when he found her drunk at a restaurant; despite insisting he was committed to Quinn, Deacon kissed Brooke, then beat a hasty retreat. Wyatt, who was aware of Deacon's history with Brooke, held Deacon's feet to the fire. After the jealous Quinn slapped Brooke to the ground, Deacon proposed to Quinn and ignored Brooke's warnings about her. Deacon admitted to Quinn that he was an alcoholic and planned to get back to his Alcoholics Anonymous meetings, where he ran into Brooke. When Brooke was tempted to drink, Deacon threw out her liquor and expressed gratitude when Brooke apologized for treating him horribly over the years. Deacon and Brooke agreed this could be their time if he wasn't engaged to Quinn; Wyatt overheard and went to Quinn, who demanded that Deacon stop supporting Brooke. Deacon assured Quinn she wasn't his second choice.
No one attended Deacon's wedding to Quinn except Wyatt, though Brooke brought Hope in on a video call to talk Deacon out of going through with it. After Hope threatened to sever their father-daughter relationship, Deacon married Quinn anyway, honeymooning quietly at home. Months later, Deacon ran into Brooke at a Forrester fashion show, happy she was maintaining her sobriety. Then, Deacon and Quinn put in appearances at Forrester's Halloween party and at Thanksgiving dinner. Off-screen, Deacon and Quinn separated, and Deacon was said to be visiting Hope in Europe.
When Deacon returned home, he visited Quinn to sign annulment papers and discovered that Quinn was harboring an amnesiac Liam so Wyatt would have a chance with Liam's estranged fiancée, Steffy Forrester. Deacon agreed to keep Quinn's secret but worried for Quinn, who seemed to be falling for Liam. Needing money, Deacon agreed to fake photos of Liam and Quinn's supposed marriage, but Deacon balked when Quinn suggested she'd have to kill Liam. Deacon had no desire to hurt his former son-in-law; Deacon swore he'd go to Bill with everything, but reluctantly worked with Quinn to position Liam on a cliff overlooking the ocean. When Liam ran off, the confused Deacon found himself plunging into the ocean after Quinn pushed Deacon off the cliff instead.
Weeks later, having survived, Deacon returned to discover that Liam had escaped and locked Quinn in a closet; Deacon threatened Quinn with an axe and seemingly refused her offer to support him if he ran off with her. But when an out-for-blood Bill summoned Deacon to grill him about the fugitive Quinn's whereabouts, Deacon kept mum, then insisted to Quinn that they had to leave Los Angeles, feeling that Quinn's lingering feelings for Liam would land her in jail.