Though little of his past is known, there are two indisputable facts about Woodruff Greenlee --- he is extremely rich and he is hopelessly devoted to his granddaughter, Greenlee.
Woodruff first surfaced in late 1999 as a somewhat dippy, hen-pecked man. In later months, Woodruff proved that he wasn't completely off his rocker --- and showed the hard-drive that made him a very wealthy man. Woodruff set up an elaborate cover with which he invested several million dollars into Ryan Lavery's Internet start-up company. He did so anonymously so that Ryan wouldn't know that Greenlee had asked him to invest the money.
After Greenlee's interest in Ryan waned, Ryan repaid Woodruff his investment in incredibledreams.com --- plus interest. Shortly thereafter, Woodruff's heart condition started acting up, but fortunately some medication pushed him back into tip-top condition. Woodruff found himself shelling out more money for his granddaughter in the summer of 2000, but this time it was for something entirely different --- ransom. Greenlee was held hostage by a sleazy underworld figure named Wade Randall and Woodruff paid $1,000,000 for her freedom. Leo du Pres ended up seizing the money from Wade and used it to take an unwitting Greenlee on a tropical vacation. When Greenlee realized the money was her grandfather's, she and Leo returned to the US --- where Leo was promptly arrested. The ransom money had been marked and Leo was tracked down as the one spending it. Woodruff offered to have the charges against Leo dropped if he agreed to never again see his granddaughter. Leo declined and, in the process, earned Woodruff's respect; he had never wanted Leo to take the money and run - it was a test of Leo's character.
Woodruff kept a relatively low profile until resurfacing in August 2003. When he returned, he made his presence known, cutting daughter Mary off from the family fortune. The move, Woody explained, was long overdue and was being done to teach Mary a lesson. The money that was to have gone to Mary was given to Greenlee.