In 1996, the first of two daughters graduated from the University of the West Indies with a Bachelor's degree in law.
At 25, she won the 1998 Miss Universe competition held at the Stan Sheriff Center in Honolulu, Hawaii. She beat off challenges from South Africa, Russia, Ireland, Brazil, India, Venezuela (the eventual runner-up Veruska Ramirez), U.S., Colombia, and Puerto Rico to win the crown. Fitzwilliam's regal air and perfect presentations won her the honor of being the second Trinidadian (and second black woman) to hold the Miss Universe title, but during the telecast her halting final answer led to the jury deadlocking between her and Veruska Ramirez of Venezuela. Because there were eight members of the panel and no way to break the tie, the higher semifinal scores, which were Fitzwilliams', became decisive.
During her reign, she was honored by the United Nations and bestowed the title of UNAIDS and UNFPA Goodwill Ambassador for her work in HIV/AIDS education and awareness.
After her reign, she recorded a jazz demo and continued her education. In 2000, she was admitted into the bar.
After her reign, she recorded a jazz demo and continued her education. In 2000, she was admitted into the bar.
She has also been appointed the Red Cross Ambassador of Youth for the Caribbean. This is the first time the Red Cross has appointed anyone to this high honorary office.
Wendy has acted as a judge and host for many regional and international pageants, such as Miss Guyana, Miss Trinidad & Tobago, and Miss Universe.
Currently, she is the Vice President of Business Development at the Evolving TecKnologies and Enterprise Development Company Limited, a state-owned company in Trinidad and Tobago. She is also attached to the Trinidad Guardian's Guardian in Education: Making a Difference project, a series of motivational school tours that also features former World Champion sprinter Ato Boldon and cyclist Michael Phillips.
In January 2006, Fitzwilliam announced that she is expecting her first child in June 2006. She appeared at the Miss Universe Guide to Beauty book launch in April 2006 and was heavily pregnant at this time. It was reported in May that Wendy gave birth to a son in the United States by many media houses in Trinidad and Tobago, this was later confirmed by her mother, Juditha Fitzwilliam.
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