Brian J. McCarthy

The sale of the Orange County Register in May was one of the latest chapters in the 300-year history of American newspapers.

And McCarthy helped to pen part of that particular piece of history.

"It was an interesting front-row seat watching the evolution of the media business in a world that's still trying to grapple with online and print," said McCarthy, who led Skadden's representation of the dismantling of Freedom Communications Inc., the final piece of which included the sale of the Orange County Register and six other papers to investor group 2100 Trust LLC, led by Aaron Kushner.

"The Freedom deal was for me the most interesting [deal of the year] because it was the most challenging," McCarthy said. "There was a long and storied history for the company in Southern California. It was a little sad to see the company go the way that it did."

That history dates to 1935, when newspaper publisher Raymond C. Hoiles purchased the Santa Ana Register and moved to Southern California. In 1950, Hoiles' various newspapers - some California-based and some out-of-state - were incorporated as Freedom Newspapers Inc. Freedom Communications filed for bankruptcy protection in 2008, and emerged in May 2010.

The Freedom Communications deal was particularly difficult, given the number of constituents involved, including shareholders, the board of directors and employees who "had to live with clouds of uncertainty" for some time, McCarthy said. His team explored various options for Freedom over a period of 18 months. All of Freedom's approximately 100 newspapers were sold after the company declared bankruptcy.

"The content that newspapers bring is critical for an informed electorate. But also, they do serve as having a unifying effect on communities," McCarthy said. "There is some new blood coming into the industry."

With newfound interest in local newspapers, McCarthy predicted the market may see similar deals in the near future.

"There has been renewed interest in community newspapers versus large dailies ... They have now gotten to prices where they are attractive to buyers," McCarthy said. "It wasn't the first [deal of its kind] and it is probably not going to be the last."

- ANDREW MCINTYRE