Leo du Pres arrived in Pine Valley on November 22, 1999. The illegitimate son of Vanessa Bennett and a married French vineyard owner, Leo was short on funds and tired of boarding school when he decided to meet his new stepfather, Palmer Cortlandt. Unfortunately, Palmer thought that Leo was Vanessa’s lover, and arranged to have it look like Leo killed Vanessa in a fit of jealousy, discovering the error just in time to take the bullet himself. When she learned of the scheme, Vanessa used Palmer’s guilt to force him to hire Leo as a VP at Cortlandt Electronics. The job didn’t last. Leo’s relationship with Vanessa was ruined when she killed her lover Paolo and was willing to let Leo take the blame and go to jail. Leo turned to his brother David for support, and left the Valley Inn to move into Erica’s house as her guest.

Leo, at loose ends again and prone to finding trouble, met up with Greenlee Smythe, and the two combined forces to win the affections of their respective crushes, the innocent Becca Tyree and Scott Chandler. Greenlee and Leo eventually consummated their friendship on more than one occasion, but deny any feelings for one another and remain devoted to pursuit of others.

Leo’s pursuit of Becca finally paid off, and the two were happy together – for about five minutes. Then Greenlee fell into bad company and Leo stood by his friend. Becca realized that Greenlee was more than a friend, and called off the budding relationship, to Leo’s dismay. He soon forgot about his disappointment as he set about rescuing Greenlee from her plight with mob-connected bad guy Wade Randall, and he and Greenlee began to realize the depth of their feelings for one another.