Tribune journalists took to the streets over the weekend to voice their disapproval of the likely sale of one of America’s largest newspaper companies to Alden, a hedge fund that has been a leading consolidator in the beleaguered local news industry.

“Just vote no!” Hartford Courant reporters chanted on a sunny Saturday afternoon in the Connecticut city. The local mayor and a senator joined in to urge shareholders of Tribune Publishing to vote against a takeover by Alden.

“Get a better buyer,” Senator Richard Blumenthal told the crowd.

The transaction would place the fate of the local US news business more firmly in the hands of financial groups. With only days to go before the shareholder vote on May 21, control of Tribune appears likely to go to Alden, the largest stockholder, which in February struck a deal to buy the rest of the company, valuing it at $630m.

If Alden takes over Tribune — owner of the Chicago Tribune, Orlando Sentinel and Hartford Courant — the hedge fund would command nearly 18 per cent of daily US newspaper circulation, estimated industry analyst Ken Doctor.

In the months after Alden’s offer was revealed, a long-shot effort to block the takeover momentarily appeared possible. Several wealthy businesspeople announced they would commit hundreds of millions of dollar to mount their own bid, in the name of protecting journalism.

But that deal fell apart last month after Swiss billionaire Hansjörg Wyss, who had offered $100m towards the offer, backed out.

The newspaper business has been shrinking for decades, as online media grew and frothy print advertising revenues dried up, leaving local papers as targets for hedge funds and private equity.

Newspaper unions across the US have lashed out at Alden in recent years, as reports swirled of heavy cost-cutting and lay-offs by the hedge fund. Tribune unions last year launched a “Save the Tribune” public relations campaign, as they sought wealthy individuals in their regions who might want to buy their local newspapers.

Three shareholder lawsuits were filed last week seeking to block the upcoming vote, alleging that Tribune “failed to disclose material information” regarding the merger.

Alden’s takeover hinges on the approval of two-thirds of shareholders, excluding the hedge fund.

Patrick Soon-Shiong remains the largest Tribune shareholder apart from Alden. The pharma billionaire and owner of the Los Angeles Times has amassed a 24 per cent stake in Tribune, giving him unique power over whether the Alden takeover goes through.

Soon-Shiong told Bloomberg this month that he had not decided how he would vote. But he would profit from the sale: he bought Tribune stock at $15 a share, below the $17.25 a share that Alden has proposed.

Mason Slaine, a Floridian tech investor who owns Tribune stock, told the Financial Times he has already voted against the Alden takeover, but with about 3 per cent of shares, he is not large enough to block the deal.

“The only one who can affect the vote significantly enough is Patrick,” said Slaine. “It looks like Alden is going to buy it. I don’t love [Alden] anyway, but they’re certainly getting a steal,” he said, referring to the hedge fund’s $630m valuation for Tribune, which he views as too low.

At the centre of the effort to block Alden’s takeover is Stewart Bainum, a Maryland hotelier who was prepared to invest $300m towards a $680m offer to buy Tribune. But while he aimed to hold on to the Baltimore Sun, Bainum’s plan hinged on lining up buyers to take control of Tribune’s other regional newspapers.

Wyss in March offered $100m towards Bainum’s bid to buy the Chicago Tribune, telling the New York Times: “I don’t want to see another newspaper that has a chance to increase the amount of truth being told to the American people going down the drain.”

However, after reviewing the Chicago Tribune’s finances during a due diligence process, Wyss pulled out.

Bainum has struggled in recent weeks to find another investor for the Chicago Tribune, according to people familiar with the matter. Without an investor for that newspaper, Bainum will be unable to proceed with his bid, these people said.