Michael W. Ferro Jr. is aggressively transforming one of the most storied publishers in the country — not least by renaming it Tronc — with plans that have excited some and befuddled others at the company.

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In early summer, after the company formerly called Tribune Publishing had rejected two takeover offers from Gannett, two of its biggest investors found themselves in an escalating dispute. The investment firm Oaktree Capital Management was publicly questioning the motives of Michael W. Ferro Jr., an investor and the new chairman of the publishing company, in his decision to rebuff Gannett.

Ferro formulated his own pointed response: During a meeting in July at his estate in Lake Geneva, Wis., he suggested to top editors and executives that their journalists investigate Oaktree and Bruce Karsh, co-chairman and co-founder of the firm, according to two people with direct knowledge of the meeting.

No damaging article about Oaktree was published, but the episode provides a glimpse into the combative business style of a relatively unknown technology entrepreneur who has become one of the country’s most significant and unpredictable media moguls.

Michael W. Ferro Jr.

Age: 50

Role: Chairman of Tronc, formerly Tribune Publishing: heads Merrick Ventures, which acquired a $44 million stake in Tribune.

Source: The New York Times

Since taking a $44 million stake in Tribune Publishing in February, Ferro has installed himself as chairman, fired the chief executive and replaced him with a longtime associate, overhauled the senior executive ranks, and reshaped the company’s board so that a majority is aligned with him.

He has also taken aggressive steps to transform one of the most storied publishers in the country, pushing a technology-driven approach to journalism that includes concepts like artificial intelligence.

And most visibly, he shed the well-known Tribune name, changing it to Tronc, for Tribune online content — a move that drew instant mockery on the internet.

Ferro declined to be interviewed for this article. A spokesman for Ferro, Dennis Culloton, denied that Ferro suggested that Tronc’s papers should investigate Oaktree.

But in conversations with more than two dozen current and former employees, Chicago businessmen, and others who know him — most of whom spoke on the condition of anonymity citing fear of retribution or continuing business connections — he emerges as an audacious businessman whose wealth of ideas can by turns impress and alienate his associates and employees.

Once a teenager who outsourced his house-painting jobs to others, Ferro, 50, has never been afraid to push boundaries. He created one of the first business-to-business internet companies, which he later sold for nearly $300 million. Emboldened by the support of Chicago billionaires, he has made moves to buy some of the city’s most iconic institutions, including the Chicago Cubs and The Chicago Sun-Times.

Over the last six months, he has appeared intent on keeping Tronc, whose papers include The Los Angeles Times and The Chicago Tribune, away from Gannett — which last week reportedly sweetened its previous $15 per share offer.

His resolve has continued to vex Oaktree, the publisher’s third-largest shareholder. In a sign of the growing distrust between Oaktree and Ferro, the firm is now conducting a review into whether he has been acting out of self-interest rather than doing what is best for shareholders.

At the same time, Ferro must contend with anxious employees who are stuck in ownership limbo as Gannett continues to circle the company, with a potential deal looming in the next few weeks.

A golden ticket

Born in 1966 in Merrick, N.Y., Ferro displayed an entrepreneurial spirit from a young age.

He graduated from high school in Naperville, Ill., and attended the University of Illinois at Chicago. In his early 20s, he started a company called Chem-Roof that made coatings to treat wood, which he sold to the Pettibone Corp., a supply and equipment company, when he was 25.

In 1996, Ferro founded Click Commerce, which used the internet to streamline buying and selling between businesses. He took the company public in 2000, at the height of the dot-com bubble, and sold it six years later to Illinois Tool Works for $292 million.

The transaction was Ferro’s golden ticket: His new wealth gained him entry into a group of Chicago business elites who were enamored with Ferro’s idea to turn the city into the next Silicon Valley.

“Chicago is founded on older-school businesses,” said Matt Maloney, a friend of Ferro’s and a founder of GrubHub, the Chicago-based online food-ordering service. “There’s an element of respect in our community for the technologists because I think it’s more novel here than in other places.”

When Ferro started a fund called Merrick Ventures to invest in tech companies, he attracted millions of dollars from Chicago business stalwarts, including John Canning, a founder of the buyout firm Madison Dearborn Partners, and Andrew McKenna, chairman emeritus of McDonald’s.

“I have a great deal of trust in him,” Canning said. “It’s never a smooth ride with Michael, but it usually ends up successfully.”

Among the fund’s first investments was a stake in Merge Healthcare, a struggling medical-imaging company.

In a pattern that presaged his actions at Tribune, Ferro became chairman of Merge and replaced almost half the board. He also installed as chief executive his colleague Justin C. Dearborn, who would later become the chief executive at Tronc. (IBM bought Merge last year for $1 billion.)

Remaking Tribune

When Ferro’s fund, Merrick Ventures, invested $44 million in Tribune Publishing in early February, he received a stake worth nearly 17 percent and the title of nonexecutive chairman, traditionally an honorary role. (To assuage antitrust concerns, he donated his stake in rival Chicago newspaper The Sun-Times to a charitable trust.)

Less than three weeks later, Tribune’s chief executive was fired and replaced by Dearborn. Ferro assumed the position of chairman and was running the company.

Tronc has since rejected two takeover offers from Gannett — the latest, in May, at a 99 percent premium. Ferro brought on another investor, Patrick Soon-Shiong, a billionaire doctor in Los Angeles, to help fend off its suitor.

Ferro’s vision for Tronc has excited some and befuddled others at the company, several current and former employees said. He has combined the role of editor and publisher across his newspapers, blurring the lines between the traditionally separate business and news sides. He said in June that he wanted Tronc to produce 2,000 videos a day, a staggering number for a newspaper publisher, using artificial intelligence.

Some current and former employees said they were impressed by his enthusiasm.

“He’s got a lot of energy and a lot of ideas,” said Anne Vasquez, chief digital officer at Tronc. “That excitement — I can feed off that excitement. The sparks begin to fly. You start to think about the possibilities as opposed to the obstacles.”

Ferro has remained committed to his plans. An employee video released in June described how Tronc would use artificial intelligence and machine learning to “allow journalists to do their jobs more efficiently.”

“The role of Tronc,” the video said, “is to transform journalism, from pixels to Pulitzers.”

The video received widespread attention online, though perhaps not in the way Ferro had hoped: It was viciously mocked for its self-importance.