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5 businesses Rupert Murdoch loved and lost

July 16, 2014: 1:17 PM ET

It's not you, it's me.

Rupert Murdoch has bought and sold more companies than anyone can remember on his way to building a vast media empire. But not all of those companies have stood the test of time.

Murdoch sent shockwaves through the entertainment industry Wednesday after 21st Century Fox (FOXA) disclosed that it had offered to buy Time Warner for the premium price of $85 billion.

Time Warner (TWX), which owns CNN and CNNMoney, rejected the offer. Fox said it's no longer in talks, but there's rampant speculation that Time Warner is now in play.

Murdoch has a reputation for not taking no for an answer. In 2007, he pushed hard to take over the Wall Street Journal publisher Dow Jones from the family that owned it. He eventually got his way. Dow Jones is now part of News Corp. (NWSA) -- which Fox split off from in 2013. (Murdoch controls both companies.)

But the octogenarian tycoon has also been known to obsess over certain assets, only to sell them at a later date when something more exciting comes along.

Here are 5 of Murdoch's "old flames":

MySpace: Before there was Facebook (FB), there was MySpace. News Corp. bought Intermix Media, which owned the early social network, for $580 million in 2005. Six years later, News Corp sold MySpace for just $35 million.

DirecTV: Before AT&T (T) recently announced plans to buy the satellite giant, there was a time when media tycoons fought over it too. Murdoch offered to buy DirecTV (DTV) for $8 billion in 2001. He was rebuffed, but he ended up taking a 34% stake in 2003. Murdoch eventually agreed to swap his stake in DirecTV with rival media mogul John Malone, who had a significant interest in News Corp at the time.

Los Angeles Dodgers: Fox bought the Dodgers for $311 million from the O'Malley family in 1998. Murdoch sold the team for $450 million to Frank McCourt, a Boston-based property developer, in 2003. The team went bankrupt in 2011 and was sold to an investment firm last year.

TV Guide: Remember when you needed a magazine to know what was on TV? In 1988, News Corp. paid a whopping $3 billion for the company that owned TV Guide. A decade later, Murdoch unloaded TV Guide for $2 billion in cash and stock to a satellite video company.

The Village Voice: It was the late 70s, and Murdoch let his hair down a bit. News Corp. bought the counter-culture publication the Village Voice for $7.6 million in 1977. Murdoch sold the Voice for $55 million in 1985 to help finance the launch of Fox broadcast network a year later.

So if Murdoch is able to convince Time Warner's board to agree to a deal, will HBO or TNT wind up being things that Murdoch unloads in a few years in order to buy the next proverbial big thing?

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Ben Rooney
Ben Rooney
Staff writer, CNNMoney

Ben Rooney is a staff writer for CNNMoney. He covers the European debt crisis and other international finance stories, in addition to writing about stocks, bonds, investing and other Wall Street-related news. Follow Ben on Twitter: @ben_rooney

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