Book of Tens: Most Intriguing Deals of the Decade

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In June 2000, Washington Post Co. paid $178 million for an acquisition billed as "an important strategic move." Dot-com digital deal? A key media property? No. The company bought Quest Education, a chain of for-profit colleges.

By last year, Washington Post was generating more than half of revenue from various Kaplan education services. Kaplan Higher Education, which began with Quest, is now Washington Post's biggest source of revenue and profits.

MDC Partners in January 2001 bought 49% of Miami shop Crispin Porter & Bogusky, giving the small agency-holding company a big stake in what would be one of the decade's highest-profile creative agencies.

The agency went on to do more attention-getting work during the decade for clients such as BMW Mini, Volkswagen and current clients such as Burger King.

When MDC bought its initial stake, Crispin Chairman Chuck Porter said, "I think it's going to be a very cool partnership." Very cool and very hot.

When a group of investors bought the Boston Red Sox in 2002 for $660 million plus the assumption of $40 million in debt, they paid more than twice what any baseball team had garnered before that point, but they still got a great deal.

The Red Sox came with the New England Sports Network, a local cable network. When the Red Sox won the World Series in 2004, the network seized the highest average season ratings among regional sports networks. It's No. 1 in ratings to this day, according to Nielsen.

To take the measure of NBC's $1.25 billion deal for Bravo in 2002, a purchase that moved NBC into entertainment programming on cable, look at this month's announcement of a different transaction: Comcast Corp.'s deal for 51% of NBC Universal, when the acquisition of the broadcast network itself got scarce attention.

Cable has been on the march this decade as broadcast networks' audiences have eroded. NBC has declined to fourth place in broadcast ratings. Good thing it has Bravo and the other cablers in its portfolio.

If at first you don't succeed, try again. Comcast in 1999 cinched a deal to buy MediaOne, a merger that would combine the No. 3 and 4 cable-systems firms into a new No. 1. Then AT&T Corp. swooped in with a higher offer for MediaOne, and Comcast abandoned its bid in return for a $1.5 billion termination fee.

But AT&T's grand schemes failed to wow Wall Street, and the company in 2000 announced a complex bust-up. Enter Comcast, which struck a deal to buy AT&T Broadband for an attractive post-bubble price.

General Motors doesn't get a lot of credit for doing things right, so let's remember that its Hughes unit developed from scratch what is now the country's largest satellite TV service and, when it came time to cash out of its investment, a compelling target for Rupert Murdoch's News Corp.

GM secured a deal giving News Corp. a 34% stake in DirecTV for $6.8 billion, which was later flipped to Liberty Media, but the '03 deal is a reminder that floundering GM has, on occasion, created real value and capitalized on it.

The smartest deal sometimes is selling, not buying. Consider Freedom Communications, owner of California's Orange County Register, controlled by the R.C. Hoiles family since 1935.

Early this decade, the family sold 48% of their shares to private equity firms before, crippled by debt amid recession and a weakening newspaper market, Freedom filed for Chapter 11 in 2009. Under a proposed reorganization, creditors would get a 98% ownership stake; the private-equity firms and family would keep 2%.

Steve Jobs spent $10 million for the computer graphics division of Lucasfilm in 1986 and made it an independent company called Pixar. So let's grant that Disney's $7.4 billion acquisition of Pixar 20 years later was lucrative for Mr. Jobs.

But Disney got its money's worth. Pixar has continued to overperform at the box office and in DVD sales. "The recent success of Pixar's 'Up' (well ahead of our forecasts) has renewed investor confidence in Disney's creative capabilities," a Pali Research analyst wrote this year.

YouTube is still trying to figure out the right ad model to cash in on the videos it hosts and plays, but Google -- which bought YouTube three years ago for $1.65 billion -- can afford to be patient.

While YouTube works on making real money from ads attached to videos, it's already collecting a pile of cash on the big rich-media ads it's been selling atop its home page since April. Google says YouTube's home page was 90% sold out over the third quarter. And YouTube collects six figures every day these ads run.

Washington Mutual collapsed in September '08, another calamity in the stunning financial crisis of fall 2008. The scale of failure was stunning; WaMu was the largest bank failure in U.S. history, with 10 times the assets of the next biggest failed bank.

The bank reopened the next morning under a new owner, JPMorgan Chase, which bought WaMu in a bargain $1.9 billion deal arranged by the FDIC. The addition of WaMu's branches gave Chase the nation's second-largest branch network, reaching 42% of the U.S. population.

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