The Pine Valley Bulletin

Portrayed by
: Josh Duhamel (1999-2002)
Family: Vanessa Bennett (Mother); David Hayward (Brother); Trey Shepherd (Brother); Frankie Stone (Cousin); Maggie Stone (Cousin)
Marriages: Laura Kirk English; Greenlee Smythe

1999: Leo duPres lived the high life in New York City. He was the son of perennial con Vanessa Bennett and Count Guy duPres, a French aristocrat who refused to leave his wife for Vanessa. Vanessa did her best to provide for her young son's lavish taste. Palmer Cortlandt, Vanessa’s new husband, got wind of their secret communications. Wrongfully believing that Leo was having an affair with Vanessa, Palmer drugged him and dragged Leo to Pine Valley. He was going to make it seem like Vanessa's young lover, Leo, killed Vanessa. When Vanessa revealed the truth about Leo, Palmer tried to stop the plot and took the bullet himself.
Vanessa found out what Palmer had done. She blackmailed him into offering Leo a position at Cortlandt Electronics.
Leo met his brother, Dr. David Hayward, for the first time. The brothers struck up an instant bond, relating their past experiences with Vanessa’s antics.

2000: Leo teamed up with Greenle Smythe to get the ones they loved. Leo wanted to date Becca Tyree, who was now dating Greenlee’s ex-beau, Scott Chandler. Greenlee wanted Ryan Lavery who was in love with Gillian Martin. Together, they plotted the breakups of their respective relationships. Scott implicated Leo in a website that took bets as to when Becca was going to loose her virginity. Leo wrongfully blamed Greenlee as the culprit.
Leo began working at Cortlandt Electronics. Adam Chandler was paying him on the side for any secrets he could pass along. Adam began to blackmail Leo. He wanted Leo to seduce a very married Marian Chandler. Leo got cold feat and hired a gigolo named Paolo to do his dirty work.Paolo was found dead and Leo was the main suspect. David came to Leo’s defense. He discovered that Vanessa was in fact locked in an affair with Paolo. Paolo had blackmailed her for money to pay off his drug debt. Vanessa was going to let Leo go to prison for a crime he did not commit.
Leo was still living with Erica Kane, David's ex-girlfriend, when her daughter Bianca Montgomery returned to Pine Valley. Leo recognized Bianca was having trouble adjusting. Bianca and Leo struck up an instant friendship. Leo learned that Bianca was a lesbian. She made Leo promise to keep his secret.
Greenlee got herself into trouble when she borrowed $1 million from a loan shark named Wade Randall to protect Ryan. Leo and Greenlee tried to scrap the money together when Wade kidnapped her. Woodfruff Greenlee, Greenlee’s grandfather, gave Leo $1 million in ransom money to save Greenlee. When Leo was able to recover Greenlee without using the money, he and Greenlee took a vacation in Caribbean. Woodfruff tracked them down having used marked bills.
Woodfruff told Leo he would not send him to prison if he never saw Greenlee again. Leo could not comply because he secretly harbored feelings for Greenlee. The feelings were mutual.
Leo became romantically linked to Laura English. Greenlee was jealous of Laura. While under the influence of Libidizone, Greenlee threw Laura off the Fidelity yacht. She blamed Bianca. Bianca revealed Greenlee threatened to tell Erica the truth about her sexuality if she told Leo the truth.

2001: Leo stole a tape that caught David drugging the punch at the launch party with Libidizone. Leo felt indebted to his brother for defending him during the Paolo scandal.
Leo mustered enough courage to tell Greenlee how he felt about her. He proposed to her and she accepted. There happiness was challenged when Greenlee’s father, Roger Smythe, returned to Pine Valley with Leo’s first wife Katerina. Katerina told Greenlee about how Leo had fleeced her of her fortune. Leo admitted he was once a con artist, just like his mother, but he had changed. Greenlee left Leo and fell into the arms of Dr. Jake Martin.
Leo continued his friendship with Laura. Laura was dying of a heart condition. Her mother, Brooke English, saw how Laura’s face glowed every time she saw Leo. As Laura’s conditioned worsened, Brooke asked Leo for a huge favor: to marry Laura. Leo wanted to make her last days happy, and agreed. They married at the hospital with David and Bianca by their side.
Leo learned that Gillian had been brought to the hospital brain dead. Leo begged Ryan to agree to let Gillian’s heart go to Laura. Gillian’s heart saved Laura.
Leo realized he did not love Laura like he loved Greenlee. He wanted out of his marriage, but did not have the heart to break the news to a fragile Laura. Greenlee arrived at Leo’s vow renewal ceremony and set off the sprinklers. At Christmas, Greenlee asked Leo to propose again.
But divorcing Laura proved to be a task in itself. Laura made false accusations against Greenlee, even filing a restraining order. Leo worried a divorce would cause Laura to finally break from reality.

2002: Leo and David rescued their cousin, Maggie Stone, from the drug lord Proteus. Maggie revealed Proteus was none other than his mother. Leo was able to stop Vaanessa before she jumped out of town. Leo still loved his mother and wanted to see he get a fair defense. Leo was weary of Vanessa’s new lawyer, Trey Kenyon. Leo did some digging into Trey’s past. He was alarmed to learn that Trey was not his real name. He was really Ben Shepherd, Vanessa’s son with Richard Field. Leo was able to look past Trey’s early deception and accept him in his growing family.
After his divorce from Laura was finalized, Leo and Greenlee quickly made plans to marry. Leo wanted his father to be at the ceremony. Leo invited Count Guy duPres, his supposed father. In reality, he was part of a cartel that wanted to get their hands on Vanessa’s Proteus fortune. At Leo and Greenlee’s wedding, Guy’s henchmen Wolfe threatened to shoot Leo if Vanessa did not reveal the location of her diamonds. Roger took the bullet for Leo. After subduing the situation, Leo and Greenlee married.
Wedded bliss was fleeting for the young couple. Vanessa successfully convinced everyone that she suffered from multiple personality disorder as a defense for her crimes. Vanessa escaped custody and took Greenlee hostage. She told Leo where her diamonds were and to meet her at Miller's Falls for an exchange. Only, it was clear to Leo that Vanessa was going to hurt Greenlee either way. Leo struggled with Vanessa for her gun. They fell over the landing and into the abyss. Leo was presumed dead.