Alden, which already holds a 31% stake in Tribune, agreed in February to pay $17.25 a share, or almost $460 million, for the stock it doesn’t yet own. The deal requires the approval of two-thirds of non-Alden shareholders, meaning Soon-Shiong, with a 24% stake, holds a virtual veto over the sale of the Chicago Tribune, New York Daily News, Baltimore Sun, and other newspapers from Connecticut to Florida.

“If Soon-Shiong doesn’t think it’s a good deal and doesn’t vote for it, it doesn’t happen,” said Rick Edmonds, a media analyst at the Poynter Institute, a nonprofit journalism school and research organization in St. Petersburg, Florida.

The math gets even tougher thanks to Mason Slaine, a Florida businessman who owns a 3.4% stake. He told the Chicago Tribune he plans to reject Alden’s offer, saying it undervalues the company. Tribune closed Thursday in New York at $17.25, the same level as the bid.

Hasn’t Decided

In a recent interview with Bloomberg News, Soon-Shiong, 68, said he hasn’t decided how he will vote. He declined to make any additional comment Thursday. A spokesman for Tribune’s special committee, which is acting on behalf of the company in the Alden proposal, declined to comment. Alden didn’t respond.

But Soon-Shiong’s role isn’t lost on Tribune journalists who have made repeated overtures to him to block Alden’s takeover. This week, Gregory Pratt, president of the Chicago Tribune Guild, published an open letter to the biotech entrepreneur, saying, “You can single-handedly keep Alden from sealing the deal.”

“We are fighting every day to keep Alden from taking full control,” wrote Pratt, who covers City Hall for the newspaper. “You can stop it. Please do.”

If shareholders reject Alden’s bid, they could be left with no buyer at all. Since March, real estate magnate Stewart Bainum Jr. has been struggling to put together a competing bid for Tribune.

Dropped Out

He teamed up with Swiss billionaire Hansjoerg Wyss on an offer of $18.50 a share, or about $680 million, topping Alden’s price. But Wyss, who was putting in about $500 million, decided not to go forward with the proposal after conducting due diligence. After that, Tribune said it ended discussions with Bainum’s investor group.

That sent Bainum searching for new partners interested in preserving local journalism. In late April, he was discussing a fresh proposal to double his commitment to a potential bid to $200 million and tap $100 million in debt financing.

But his goal has been to find local owners for all of the Tribune newspapers, and he has struggled to find a buyer for the Chicago Tribune, according to a person familiar with the matter.

“It’s possible, with more time, that Bainum could be able to put a bid together,” Edmonds said. “But nobody in Chicago is stepping up.”

Bainum declined to comment through a representative.

The past week has seen a flurry of last-minute attempts to stop Alden. Tribune said some shareholders had filed lawsuits to block it. State treasurers in Maryland, Connecticut and Illinois — all markets with Tribune newspapers — signed a letter urging the board to consider Bainum’s bid.

“We are concerned that the Alden bid would not be in the best interests of Tribune shareholders or the communities it serves,” they said.

Journalists Rally

And Tribune journalists rallied across the country, urging investors to reject Alden’s offer. In Chicago, they held signs that said, “Vote No to Alden” and “Save Local News.”

With the clock running out and Friday’s vote looming, it looks like it will be Soon-Shiong who decides. Slaine told Bloomberg News in March that the doctor-turned-entrepreneur likely hadn’t thought much about his Tribune stake yet.

“He’s very focused on things like Covid vaccines, which is way more important than this,” Slaine said.