On May 20, Boston Red Sox and Fenway Sports Group (FSG) owner John Henry received the Lifetime Achievement Award at the 2026 Sports Business Awards. Most Red Sox fans would agree that he's earned the award — Henry was a huge part of the shattering of the Curse of the Bambino in 2004 and he turned the Red Sox into the winningest team in terms of championships since 2000.
According to Chris Cotillo of MassLive, Henry was introduced by David Ortiz at the event and he followed with an acceptance speech, during which he uttered a quote that Sox fans haven't taken well.
"When I arrived in Boston 25 years ago, I was told, 'If you win the World Series in Boston, you'll never have to buy another drink in this town. It doesn't actually work that way," Henry said (via Cotillo).
Maybe fans would've bought Henry a drink or two 22 years ago right when the Curse was broken, or as recently as 2018 when the winningest Boston team in history took home a fourth World Series in 14 years. But Henry has done more than enough to lose favor with Red Sox fans between then and now.
Red Sox fans are rolling their eyes at yet another tone-deaf comment from John Henry
Beyond Red Sox fans' current feelings towards Henry, his net worth is approaching six billion dollars ($5,700,000,000), according to Forbes. The last thing anyone in the world needs to be doing is buying drinks for a man with more money than god.
Henry is also perfectly aware that Red Sox fans are exhausted by his recent changes to the state of the organization. Henry purchased many other sports teams or stakes in different leagues through FSG, which has split finances and priorities between all the interests. He sold parts of the team to private equity firms. Boston hasn't signed a major free agent to a long-term deal in years and the 2018 team is entirely dismantled — all to hold onto as much money as possible.
The Red Sox haven't made a meaningful run in the playoffs since 2021, but not for a lack of luck or success, but a complete lack of effort. Henry has heard fan criticism about his approach and spending changes for so long that he's decided he's done listening — he hasn't answered questions from Red Sox media since 2020, he axed his appearances at Winter Weekend, the Red Sox's former fan festival, before changing the format altogether to avoid accountability for his decisions.
It shouldn't be surprising that no Red Sox fans are rushing to buy Henry a drink, despite the four championships he's helped bring to Boston. Accountability and people skills are important, and winning isn't everything — effort counts for something, and Red Sox fans haven't seen enough care in recent years.
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