Feb 17, 2025; Lee County, FL, USA; Boston Red Sox owner John W. Henry attends spring training at Jet Blue Park at Fenway South. Photo Credit: Chris Tilley-Imagn Images Chris Tilley-Imagn Images
The John Henry era with the Boston Red Sox has gone through plenty of different variations.
Henry, as the principal owner, purchased the Red Sox way back in 2001 along with Tom Werner and a group of investors. At the time, the Red Sox were still dealing with the Curse of the Bambino and hadn’t won a World Series title since 1918. Over the last 25 years, we’ve seen some of the highest points for the Red Sox as a franchise, and also some of the lowest moments. On the high side, Boston has won four titles with Henry as the principal owner (2004, 2007, 2013, and 2018).
Since 2019, though, there has been a lot of negative for the club. The trade sending Mookie Betts to the Los Angeles Dodgers has been the most public misstep by the team in recent memory. But Boston has just two playoff appearances since 2018 (2021 and 2025) and also has been big-name guys go elsewhere either in free agency or by way of the trade, like Rafael Devers, Xander Bogaerts, Chris Sale, and Alex Bregman, among many others.
Boston fans have been all over Henry and the Red Sox in general for years at this point. The club hasn’t spent at the same levels as it used to and with Fenway Sports Group expanding beyond baseball, it has led to hard feelings. The Red Sox won 89 games last season, but followed up with an offseason in which Bregman walked and now are 22-27. Plus, of course, Boston fired manager Alex Cora as well.
The Red Sox Aren’t Where They Want To Be
The vibes around Boston aren’t very high right now and that is because of a build-up of issues between the team and fanbase since 2019. On Wednesday, Henry received a Lifetime Achievement Award at the 2026 Sports Business Awards and had a bit of a tone-deaf comment towards the fanbase, as transcribed by Chris Cotillo of MassLive.com.
“John Henry received the Lifetime Achievement Award, given to him at the 2026 Sports Business Awards, presented by Sports Business Journal last night,” Cotillo wrote on X. “He was introduced by David Ortiz and gave an acceptance speech.
“Henry: ‘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 isn’t necessarily wrong. In the grand scheme of things, he will be remembered fondly in Boston and should get credit for the fact that he has helped lead the club to four championships since he took over. But that doesn’t remove recency bias. He is still the principal owner of the team. He should get credit for the past success, but with him still being the owner, that means he also gets the heat for the recent failures.
Whether fair or not, Henry and the Red Sox have been perceived poorly for a while now. This type of comment isn’t even that far off. But with the team sitting five games below .500, it’s not the time. Again, he helped to bring four championships to town, but that doesn’t give a pass for some down years.
