Overstock.com Announces Winner of 2008 $50,000 Family Bailout Sweepstakes

CEO personally presents award to sweepstakes winner in Phoenix, AZ

SALT LAKE CITY, Jan. 5 /PRNewswire-FirstCall/ -- Overstock.com, Inc. (NASDAQ: OSTK) today announced Ramona Kako of Phoenix, AZ has won the Overstock.com $50,000 Family Bailout Sweepstakes. Overstock.com will pay the $50,000 directly to one or more qualified creditors of Kako.

Kako, a mother of two, works multiple jobs while her husband works as a plumber and attends school for his journeyman license.

Overstock.com Chairman and CEO, Patrick M. Byrne personally presented the $50,000 award on the doorstep of Kako's home in Phoenix.

"We're thrilled to have found such a deserving and hard working American family," said Byrne. "We're hoping that this bailout will have a significant impact on their lives."

Overstock.com created the Family Bailout plan in order to give those who visit Overstock.com the chance to pay off their mortgage, credit cards, or other large debts in the currently troubled economic times.

"Thank you, Overstock," said Kako. "This will help our family so much."

About Overstock.com

Overstock.com, Inc. is an online retailer offering brand-name merchandise at discount prices. The company offers its customers an opportunity to shop for bargains conveniently, while offering its suppliers an alternative inventory distribution channel. Overstock.com, headquartered in Salt Lake City, is a publicly traded company listed on the NASDAQ Global Market System and can be found online at http://www.overstock.com. Overstock.com regularly posts information about the company and other related matters on its website under the heading "Investor Relations."

Overstock.com(R) is a registered trademark of Overstock.com, Inc.

This press release contains certain forward-looking statements within the meaning of Section 27A of the Securities Act of 1933 and Section 21E of the Securities Exchange Act of 1934. Such forward-looking statements include, but are not limited to, statements regarding the deservedness of the recipient. Our Form 10-K for the year ended December 31, 2007, our subsequent quarterly reports on Form 10-Q, or any amendments thereto, and our other subsequent filings with the Securities and Exchange Commission identify important factors that could cause our actual results to differ materially from those contained in our projections, estimates or forward-looking statements.