John Tomase

After Orioles sale, is it time for John Henry and Red Sox to follow suit?

The Red Sox owner has his work cut out for him, to say the least.

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They're popping crab cakes in Baltimore this morning after learning the Orioles will be sold for nearly $2 billion to a local group that includes franchise icon Cal Ripken. The new owners will displace the dysfunctional Angelos family and inherit one of baseball's best young rosters.

It's enough to make a Red Sox fan spit.

For nearly two decades, no one questioned John Henry's stewardship, but as the Red Sox refuse to spend in free agency and their grand plan to rebuild hinges exclusively on three good-but-maybe-not-great prospects, we're left to wonder: Would the Red Sox be better off with new ownership, too?

As it is, their job is about to get a lot harder. The Orioles, incredibly, have not signed a single free agent to a multi-year contract since Mike Elias took over baseball operations in 2018. But what they have done is build a Death Star of a minor-league system that just keeps pumping out No. 1 overall prospects like TIE fighters, the latest being Jackson (son of former All-Star Matt) Holliday.

The Orioles won 101 games last year without really acquiring anyone of note, and the prospect of them suddenly spending should send a shudder from Tampa to Toronto and points northeast.

It also potentially pushes the Red Sox even further down the AL East pecking order, with the very real possibility that someday soon they could own the division's fourth-highest payroll, ahead of only the impoverished Rays.

That they're doing so willingly remains borderline heartbreaking, and signals a change in philosophy that could doom them to second-division status for years, which raises the question: What's the point?

Why own the Red Sox (valuation: $4.5 billion) if you're going to treat them like a mid-market team? What's the point of overseeing one of baseball's signature franchises if the goal is simply winning 85 games and hoping to pull a Diamondbacks in October? Why cycle through chief baseball officers if you're not going to let any of them try?

It distinctly feels like Henry's heart isn't in it anymore, despite assurances from chairman Tom Werner that they plan to own the Red Sox for another 20 years. So what's the point?

Red Sox chairman Tom Werner and president/CEO Sam Kennedy
Billie Weiss/Boston Red Sox/Getty Images
John Henry didn't attend the Red Sox' Winter Weekend in 2024, leaving chairman Tom Werner and CEO Sam Kennedy to face the fans and media.

Henry's attention is certainly everywhere else, with the latest object of his affection a $3 billion stake in the PGA Tour that would add golf to Fenway Sports Group's unwieldy portfolio, which is experiencing a time of general turmoil. In addition to unhappy Red Sox fans, Henry must also handle the fallout of head coach Jurgen Klopp's shocking departure from Liverpool, as well as his Penguins being on pace to miss the NHL playoffs for the second straight year after 16 consecutive postseason appearances. Hell, even FSG partner LeBron James might miss the playoffs with the Lakers.

The Red Sox feel increasingly dysfunctional, and the Orioles demonstrate where too much dysfunction leads. The squabbling sons of Peter Angelos stepped in it at every turn, from suing each other for control of the team, to being in a perpetual dispute with the neighboring Nationals over shared TV rights, to nearly letting the lease on Camden Yards expire.

They've devoted embarrassingly few resources to the big league roster, spending less than everyone except the itinerant A's last year, but winning anyway because of their incredible farm system. They're about to start paying arbitration awards, however, and now would be the time to negotiate extensions with young stars like catcher Adley Rutschman and reigning Rookie of the Year Gunnar Henderson before they price themselves out of town.

That would've been a shaky proposition under the stingy John Angelos, but everything is on the table with billionaire Baltimore native David Rubenstein about to claim a stake in the franchise. Imagine if he starts adding talent, too? The Orioles could use a free-agent ace like Jordan Montgomery or Blake Snell every bit as much as the Red Sox, and only one of those teams just won 101 games.

The Orioles ownership situation remains complicated, since Rubenstein's group reportedly won't take complete control from the Angelos family until the 94-year-old patriarch dies, a ghoulish provision that will help his children avoid a hefty tax bill, because hey, this is America.

Either way, Orioles fans can officially start dreaming of a new day, with an owner who may actually think big again. Their Red Sox counterparts share no such optimism, unless Henry either changes his ways and invests in the product, or changes his mind and puts the team up for sale.

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