The Deal From Hell: How Moguls and Wall Street Plundered Great American Newspapers by James O’Shea | Public Affairs | 395 pages, $28.99

Many in the journalism craft have watched the decade-long struggles of Chicago’s Tribune Company with bewilderment, incredulity, and occasional gasps of horror. The story begins with Tribune, solidly profitable and staidly Midwestern in its values, swooping west to buy the parent company of the Los Angeles Times before the CEO realizes it’s for sale—stabbed in the back by his largest stockholders, the coupon-clipping cousins of Otis Chandler, great-grandson of Times Mirror’s original president. On creativity alone, it qualified as a brilliant coup. Not even Otis knew the Chandlers could sell their Times Mirror stock. The deal created the nation’s third-biggest newspaper and television powerhouse.

Closing the deal proved to be the last happy moment Tribune would savor. The suits in Tribune Tower dreamed of merging rival journalism cultures, heartland and left coast, into one contented, synergistic family. That never happened. The Chandlers’ addiction to fat dividends burned Tribune, as it had Times Mirror, and led to the emergence of CEO Sam Zell as, arguably, America’s most ill-suited media mogul. He openly loathed the journalists he employed, replaced Tribune’s old-line Republican executives with uncouth ex-radio hacks, and burdened the company with huge debt. For three years now, Zell’s Tribune has lingered in bankruptcy.

In The Deal From Hell, James O’Shea gives many of the gory details. The title comes from Zell’s reflective quip about his media ownership dalliance. O’Shea puts the label on the whole mess, which he saw up close as a Chicago Tribune senior editor, as newspaper tutor to Tribune CEOs, and as Chicago’s temporary ambassador to the rebellious Los Angeles newsroom. He was a Chicago partisan who initially celebrated his employer’s ambitions—and who relished the chance to humble swelled heads in La-La-Land—until he came to believe that journalism itself was in peril from the likes of Zell and excessive corporate focus on the bottom line.

The book’s subtitle, How Moguls and Wall Street Plundered Great American Newspapers, suggests ransacking outside invaders. But the tale in it is more about self-inflicted damage from executives, like ex-Tribune CEO Dennis FitzSimons, who fancied themselves as visionaries, but who were more consumed with personal crusades and petty jealousies than with addressing the challenges and opportunities of the digital age. While they tinkered, Tribune’s managers let themselves be blindsided by larger forces that changed the rules of the media game.

Like many Tribune watchers, I had hoped someone would write a behind-the-scenes book about the company’s troubles. I began at the Times as a college intern and stayed for twenty-five years, as a Metro reporter, roving correspondent, state desk editor, and senior projects editor. I left for The Industry Standard a few months into Tribune’s ownership; when the tech bubble burst, taking my new employer with it, I started LA Observed, a blog monitoring the local news scene. The tensions between Tribune and my friends and former colleagues at the Times quickly became the biggest media story in town. O’Shea reveals enough juicy details that his Chicago perspective keeps even a biased Angeleno engaged.

The deal from hell, as O’Shea tells it, begins to come together in April, 1999. Tribune held a nice package of papers and TV stations, but CEO John Madigan craved more. He requested a meeting with Mark Willes, CEO of Times Mirror, parent of the Times, Newsday, The Baltimore Sun, and a few smaller newspapers. As the CEOs sat down, Craig Newmark was filing the papers to create Craigslist. Stanford grad students Sergey Brin and Larry Page were preparing to announce Google’s initial public funding. And a gift shop clerk in Hollywood was gaining traction for a conservative-leaning news aggregator. His name: Matt Drudge.