Drew Annese

An Open Letter to John Henry Dear John, I am 52 years old, the same age you were when you bought the Boston Red Sox. That parallel has been on my mind lately, because at 52, you changed the trajectory of a franchise and, in a very real way, the emotional lives of millions of fans like me. My father passed away in 2021. Because of the choices you, Larry Lucchino, and Tom Werner made, he and I were able to share something we never thought we would see together: a winning Red Sox team. For most of my dad’s adult life, and for the first 30 years of mine, we lived with the assumption that the Red Sox simply did not win titles. We hoped, we joked, we endured heartbreak, but deep down we accepted that it might never happen — and if it did, it would be in an alternate dimension or something. Then it happened. It really happened. Not once, but four times. Those championships were not abstract achievements. They were nights on the couch, phone calls, laughter, disbelief, and relief. They were memories I still carry now that my father is gone. That is something no owner can ever fully measure, and something no fan should forget. For that, you deserve real thanks. When you bought the Boston Red Sox, you were a disruptor with conviction, appetite for risk, and a clear belief that bold decisions could rewrite history. You proved it. You are 76 now. Time changes all of us. I don’t mean to get overly clinical — I’m a copywriter who does a lot of work in the healthcare space — but research is clear that as we age, dopamine levels naturally decline, and with that comes a shift in how we assess risk. Fewer decisions are driven by the upside of reward. More are shaped by the fear of loss. That is human. It is understandable. But it is also visible. It is also fair to say that some of your ownership group’s old fire may be gone in the wake of Larry Lucchino’s passing. He left a real void in that department. You, Larry, and Tom Werner were a formidable force. Together, you changed baseball in Boston forever. Sadly, your recent Red Sox teams have instead felt managed to avoid mistakes, not built to chase greatness. In light of Alex Bregman’s regrettable departure for Chicago, I would like to propose that you sign Bo Bichette. Give him an eight-year, $320 million contract. Maybe that’ll do it. If he wants 10 years, give him 10 years. Give him what it takes. If the deal turns out to be an overpay, consider it a self-imposed tax for failing, in recent years, to be aggressive enough to win the way you once were. What is the real risk in a deal like that? How involved do you realistically expect to be with this team at the end of that deal, when you are 84 years old? If Bo Bichette can’t be acquired, please pursue any and all other similarly aggressive avenues to improve this baseball team. Championships are not won by protecting balance sheets. They are won by conviction. And by good baseball players. Baseball is a game of failure. Not every deal will work out. Even some of the best teams fail to win it all. But if you are concerned with your legacy, which is worse: Trying to win, but failing? Or losing interest in even trying? This is not a criticism as much as it’s a plea for clarity. Red Sox fans love the Red Sox. We always have. We always will. Do you still? Regards, Bill Colrus (AKA @SawxSouth)