Overstock.com Announces Winner of July $10,000 Family Bailout Sweepstakes

Plans to Continue Monthly Sweepstakes Through December 2009

SALT LAKE CITY, Aug. 27 /PRNewswire-FirstCall/ -- Overstock.com, Inc. (Nasdaq:
OSTK) announced today that Bob Romain of Metamora, Michigan has won the July
2009 $10,000 Family Bailout Sweepstakes. Overstock.com will pay the $10,000
directly to one or more qualified creditors of Romains' choice.

Romain, retired after 35 years at General Motors, is the father and
grandfather of a large, close-knit family who hit hard times when the terms of
his retirement plan changed as a result of the recent GM restructuring.
Romain has worked hard his entire life to provide for his family, and now
worries that he will be unable to continue to do so. Romain plans on using
the $10,000 to pay off his bills.

Approximately 250,000 people entered the July sweepstakes. Romain was
selected as the winner according to contest rules. No purchase was necessary
for eligibility. To enter the August $10,000 Family Bailout Sweepstakes go to
www.overstock.com/familybailout. Additionally, shoppers will have the choice
to opt-in to the contest when purchasing items through Overstock.com.

"Romain is a hard working American," said Patrick Byrne, CEO and Chairman of
Overstock.com. "We hope this $10,000 will help him and his family during these
trying times."

In January of this year Overstock.com created the Family Bailout Sweepstakes
in order to give Overstock.com visitors the chance to pay off their mortgage,
credit cards, or other large debts.

"This $10,000 will be a huge benefit to me and my family," said Romain. "Thank
you, Overstock.com!"

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. All other
trademarks are the property of their registered owners.

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 continuation of the sweepstakes. Our
Form 10-K/A for the year ended December 31, 2008, 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.

SOURCE Overstock.com, Inc.

Media, Roger Johnson, +1-801-947-4430, rojohnson@overstock.com, or Investors,
Kevin Moon, +1-801-947-3282, kmoon@overstock.com, both of Overstock.com, Inc