In Boston, there’s a billionaire who’s well-known… yet little-known. John Henry isn’t flashy, doesn’t like appearing on magazine covers with shocking statements, and rarely steps out in public to justify his decisions. He’s the city’s “quiet sports billionaire”—the man behind the Boston Red Sox, Liverpool FC, massive yachts, and countless global sporting assets. But for many Bostonians, John Henry’s most important asset isn’t on the field or baseball pitch.
It’s in… the newspapers.
John Henry has always been a controversial figure among Red Sox fans. Every transfer window, every time a star leaves, the complaints resurface: “He won’t spend the money,” “He couldn’t keep Alex Bregman forever,” “A stingy owner in the age of billionaires.”
It’s all part of the game of owning a team. When you own a cultural icon like the Red Sox, you’re never left in peace. People mention John Henry’s yacht – rumored to be as long as two city blocks – as a sarcastic reference to the unsigned contracts.
But amidst all that controversy, there’s something less talked about – and perhaps far more important.
When John Henry bought The Boston Globe, many considered it just a side investment. He spent $70 million – a figure that Boston sports circles jokingly say is only equivalent to two years’ salary for a third-base B-list star.
A few years later, Henry sold the Globe’s real estate holdings for $80 million, a profit on paper. But the point isn’t the profit. The point is: he didn’t ruin it.
In an era where local journalism was dying, stifled by investment funds, clickbait, layoffs, and political pressure, the Boston Globe remained… the Boston Globe. A serious newspaper. A truly functioning newsroom. A place where journalists could still do their job.
John Henry’s greatest value to the Boston Globe probably lay in what he didn’t interfere with. He didn’t turn the newspaper into a PR tool. He didn’t force editorial direction. He didn’t manipulate stories to serve personal or sporting interests.
His wife, Linda, was involved in the Globe’s operations – but by all indications, it was a constructive, not controlling, involvement. While countless newspapers, large and small, across America are floundering—shaking, shrinking, distorting—the Globe has maintained its identity, staff, and ambition.
The clearest proof? More than a dozen Globe reporters are at the Super Bowl right now. In 2026. When many other news organizations no longer have the budget to send a reporter on assignment.
In the current context, this is exceptional. John Henry isn’t the kind of billionaire lining up in the newly gilded corridors of power in Washington. He doesn’t appear in scandalous dossiers. He doesn’t rent out Venice for a lavish wedding. He doesn’t spend $75 million on a biographical film about a controversial figure.
And most importantly: he still owns a fully functioning newspaper.
That sounds like a low standard. But in 2026, that’s almost a miracle.
The Red Sox might win or lose. Liverpool might win or lose. Sports teams are cyclical. But a newspaper that survives, remains independent, and takes its work seriously in this day and age is what leaves a lasting legacy.
John Henry may be criticized for his transfer spending. He may be booed every time a star leaves. But in another corner of Boston – quietly, persistently – he is doing what very few billionaires are willing to do: letting journalism be journalism.
No need for fanfare. No need for monuments. Just acknowledgment of one simple thing: among America’s many sports billionaires, John Henry is holding – and protecting – something increasingly rare.
A newspaper that still operates. A local press that hasn’t been corrupted. And a city that still has a place to tell its own story.
Kudos, John Henry. Perhaps that’s the most valuable contract you ever signed.
