1999: Vanessa Bennett made a life for herself by going from one rich man to another. Whenever her cash flow was compromised, she knew that she could turn back to her son, David Hayward, for help. But David had moved on this time. He had established himself as a respected doctor, just like his father, the late Charles Hayward; the father Vanessa had coaxed into suicide for his fortune.
Vanessa found her new meal ticket in David’s lover, former model Erica Kane. Secretly, Vanessa used her friendship with Erica to sell information to an author writing a tell-all biography. Opal Cortlandt was weary of Vanessa’s sudden closeness to Erica. Vanessa was also romantically linked to Opal’s ex-husband, Palmer Cortlandt.
Vanessa convinced Palmer to elope with her. Palmer became suspicious of Vanessa’s secret communications with a man in New York. Palmer thought she was having an affair. In reality, Vanessa was hiding her other son, Leo duPres. Palmer drugged Leo and dragged him to Pine Valley to reveal Vanessa’s supposed infidelity. Vanessa revealed the truth to Palmer. At the same event, Palmer was shot.
Vanessa realized that Palmer had tried to kill her and frame Leo. She used the information to blackmail Palmer into staying in their loveless marriage, and to get Leo a starting position at Cortlandt Electronics.

2000 : Vanessa pushed her luck when she began an affair with a gigolo named Paolo. When Paolo was found dead, she left Leo to take the fall for the crime. Vanessa had accidentally killed Paolo after he tried to blackmail her over their liasons. Though Vanessa was not convicted of the crime, she still lost out. Leo did not want to have any contact with her. Palmer cut off her spending and sold off her expensive clothes.
Vanessa learned that Arlene Chandler had miscarried Adam Chandler’s baby. Vanessa promised to keep her secret, for a price. She blackmailed Arlene to maintain her lavish lifestyle. All the while, they supported each other's plots to hang onto their dysfuntional marriages.

2001: Adam Chandler’s hired goons wrongfully shot Vanessa thinking she was Arlene. Palmer nursed his wife to health. The ordeal saved their crumbling marriage.
Though Vanessa was now one of the richest women in the world, she could not escape one of her darkest secrets. For years, she operated a drug ring under the codename "Proteus," with her late husband, Charles. She was bringing her lucrative business to Pine Valley. Already, she was secretly filtering shipments through Erica’s company Enchantment. She wanted to use Mateo Santos’ club, SOS, for a front in her operations. She hired Roger Smythe as her gopher. But Roger was incompetent and was caught. To make Mateo comply with her requests, Vanessa began to threaten his family.
Vanessa’s niece Frankie Stone made herself at home at the Cortlandt Manor. Frankie proved to be a formidable con-artist by faking a car crash with Erica and sleeping with her daughter, Bianca Montgomery.

2002: Knowing the authorities were closing in, Vanessa decided to cut her losses and go on the run. She sent her driver to kill Mateo. Before skipping town, her other niece, Maggie Stone, confronted her. Maggie knew that Vanessa had killed Frankie because she had uncovered her identity as Proteus. Vanessa overtook Maggie and left her in a steam room to die. Leo caught up with Vanessa and stood in her way of escape. Vanessa threatened to kill Leo if he did not let her go, but he knew she would never kill her own son.
At the hospital, Vanessa feigned multiple personality disorder for a future defense. Vanessa’s lawyer, Trey Kenyon, wised up to her plots. Vanessa felt strange around Trey. She realized that Trey was her son from an affair with Richard Fields. She admitted she was with Richard the night he raped Erica over thirty years ago. Richard held her movie career in his hands, so she did not report him. Trey came to Pine Valley on a mission of revenge. He intended to steal Vanessa’s Proteus fortune, which Vanessa kept in the form of diamonds.
But Trey was not the only one after Vanessa’s stash. A terrorist named Wolfe took Vanessa hostage and forced her to reveal the location of the diamonds less he kill Leo. Roger intervened and took the bullet for her son. After nearly drying from Wolfe’s poison, Vanessa let on a kind persona named "Nessa." Instead of going to prison, she went to a safe house. Vanessa easily escaped.
Knowing Leo was the one person who could stop her, Vanessa kidnapped his wife, Greenlee duPres, and held her hostage on Miller Falls. She would not harm Greenlee as long as Leo gave her the diamonds and helped her escape authorities. When Leo arrived, a struggled ensued for Vanessa’s gun. The railing on the observation deck broke and mother and son fell into the abyss below. Both were presumed dead.