Mr. Ferro is so sure of his plans for his company — which include the combining of the editor and publishers at its newspapers, using artificial intelligence and a pledge to open bureaus for The Los Angeles Times in places like Lagos and Hong Kong — that he rebuffed overtures from Gannett that would have given shareholders a rich premium. Gannett's revised offer of $ 15 a share, from the $ 12.25 a share Tribune rejected in early May, represented a 99 percent premium to the closing price on the last trading day before Gannett went public with its initial offer.
Also on Thursday, a shareholder sued members of the board, including Mr. Ferro, for breaching their fiduciary duties in potentially blocking the takeover.
Tribune is not Mr. Ferro's first foray into the newspaper business. In late 2011, a company called Wrapports, led by Mr. Ferro and Timothy P. Knight, a former publisher of Newsday, agreed to buy The Chicago Sun-Times, the city's second-biggest paper. He emulated a Silicon Valley atmosphere, creating an arcade game room and providing free candy and ice cream.
Some aspects of Mr. Ferro, however, can seem decidedly retro. He has been known to publicly comment on women's physical appearances. While Mr. Ferro was making a presentation to the City Club of Chicago several years ago, for instance, he pointed to a picture of a female Sun-Times reporter and said "she's even better looking in person," according to a YouTube video of the event. (Mr. Zell's ownership of Tribune was characterized by, among other things, a work environment that many thought was demeaning toward women.)
Mr. Ferro wears the uniform of a tech entrepreneur — which is what he was until about a decade ago. He sold Click Commerce, which made software to manage supply chains, to Illinois Tool Works for about $ 300 million (an investment that I.T.W. had to write down two years later).
That made him a millionaire many times over and Mr. Ferro used his newfound status to take seats on boards across the city, becoming intertwined with the small club of Chicago's wealthy business elite.
"Michael's punched his ticket at all these institutions that these movers and shakers are involved in," said James O'Shea, a former managing editor at The Chicago Tribune who has worked with Mr. Ferro. "He does know his way around the city."
Mr. Ferro, known for his salesmanship, persuaded the likes of John Canning, founder of the private equity firm Madison Dearborn Partners, and Andrew McKenna, chairman of McDonald's, to put capital into his new investment firm.
Merrick Ventures, as it was known, quickly made a notable bet on a company called Merge Healthcare. Mr. Ferro took a controlling stake in the company, which made medical-imaging software, and ousted the chief executive, installing his own associate, Justin Dearborn. That was a precursor to a strikingly similar move Mr. Ferro made at Tribune, where Mr. Dearborn is now the chief executive.
Mr. Ferro's stature among some in the elite Chicago community started to fade after regulators questioned Merge's related-party transactions. From a financial perspective, the deal was seen as a success. Merge sold to IBM for $ 1 billion last year, a 900 percent return from the time he invested.
In autumn 2015, Tribune Publishing announced a staff reduction plan as it faced questions about how to bolster its media properties and raise its stock price. Tension between the company and its California papers was also high. The publisher of The Los Angeles Times was fired after only a year in the job and there were disagreements about financial projections.
In February, Mr. Ferro again opened his checkbook — this time for Tribune. At the time, Tribune's board voted for his $ 44.4 million private placement at $ 8.50 a share. Mr. Ferro transferred his equity in the Sun-Times into a charitable trust. About three weeks later, Jack Griffin was fired as chief executive and Mr. Dearborn stepped in.
Not long after, Gannett saw an opportunity and made its move. Its first offer of $ 12.25 a share was quickly rejected, so the company, which is based in McLean, Va., increased it several weeks later to $ 15 a share. The intermittent dueling news releases made it clear that Mr. Ferro did not want to engage with Gannett unless he "got a piece of the action."
To fend off Gannett, Tribune issued almost five million shares to an investor, Dr. Patrick Soon-Shiong, who agreed to side with Mr. Ferro on major issues. Together the two controlled nearly one-third of Tribune shares.
For Gannett, owning Tribune's newspapers would give it a larger national footprint, as well as publications in metropolitan markets, including Baltimore and Orlando, Fla., which could help it appeal more to national advertisers. If it decides to walk away from its takeover attempt, it could still buy other newspaper companies to expand its reach, though perhaps none would have quite the same prestige as Tribune.
"Tribune was big, and it was a way to pick up a lot of scale potentially in one fell swoop," said Barry Lucas, an analyst at Gabelli & Company. "But there are other ways to make this work."
There could also be another twist: Mr. Ferro has indicated his own interest in buying Gannett.
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