Holly began her professional wrestling career in WCW, where she also worked as a trainer. In 2000, Greenwald debuted in the then-WWF as part of the The Holly Cousins Stable, an alliance of storyline cousins. She was later aligned with The Hurricane. During her time with the WWF/WWE, Holly held the WWF Hardcore Championship once and the WWE Women's Championship twice.
After leaving the wrestling business, Greenwald has made sporadic wrestling appearances. She is a landlady for her property holdings. Greenwald is a born again Christian. She now works for Minnesota Teen Challenge. A one-year residential drug and alcohol rehabilitation program.
In July 2010, she announced her engagement to Geno Benshoof, whom she met while working as a teen counselor. The couple were married in the backyard of Benshoof's parents house in White Bear Lake, MN on July 22, 2010.
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