Throwing money at problems does not always solve them, but they can provide a great, temporary fix. That seems to be the case with the most marquee teams in MLB. The New York Yankees have been defined by this ever since the late George Steinbrenner bought the team, or at least since Scott Boras decided everyone of his clients needed every last stinking dollar. Where has that gotten them?
Since three-peating as World Series champions from 1998 to 2000, the Yankees have won precisely one world championship, and that came nearly two decades ago. 2009 was a long time ago. In the years since, the arch rival Boston Red Sox have won two World Series, amid their perpetual up and down nature. While the Toronto Blue Jays are now on top of the division, all eyes are on the Red Sox.
After giving heaping sums of cash to unproven rookie Kristian Campbell out of my high school, the Red Sox decided to do the great Alex Anthopoulos thing again by extending an emerging star player well before he is ready for it. Yes, the Red Sox have decided to give outfielder Roman Anthony an eight-year, $130 million extension before the end of his rookie year. What could possibly go wrong?
At the very least, the deal is team-friendly. Plus, it does extend the Red Sox's competitive life cycle.
BREAKING: Outfielder Roman Anthony and the Boston Red Sox are finalizing an eight-year, $130 million contract extension, sources tell ESPN. The deal, which is pending a physical, includes a club option and will keep Anthony under team control through 2034.
— Jeff Passan (@JeffPassan) August 6, 2025
Like the Yankees, the Red Sox probably need a new manager for any of this to matter, but yay! money!
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Roman Anthony could extend Boston Red Sox's World Series window
I am in the extreme minority when it comes to two very important topics in baseball. Prospects do nothing for me, and I would be incredibly reluctant to give any player more than a five-year deal in any sport. Injuries are a part of every game, so why guarantee anything more than the length of a great player's prime in terms of years? I understand it is all about team control at a fair price, but not for me.
Anthony may very well become the greatest thing to happen to the Red Sox since Nomar Garciaparra, but we have all seen how quickly things can turn for the worse in one's career. Garciaparra should have been on the 2004 World Series Championship team, but his eventual decline was already well underway. That being said, I do respect the Red Sox for having the stones to make a big deal like this.
Again, these type of contracts are not for me. How many Michael Harris IIs, Austin Rileys and Spencer Striders does your favorite team need to grossly and prematurely overpay before you get the point? You should be paying your homegrown stars the big bucks when they are in their primes like Freddie Freeman and Max Fried. Locking yourself into a major contract with a young player is risky business.
However, I do feel more optimistic about the Red Sox's long-term viability over the Yankees. Aaron Boone has become a long lost item in the back of your fridge. Brian Cashman gets to operate with no consequence in the front office like he is the Chris Ballard of MLB. While I do believe that Alex Cora will inevitably thumbscrew it to oblivion like Ross Geller of Friends, he will keep holding the team back.
In the end, Boston's World Series window is starting to open, whereas the Yankees' is starting to close. For an NFL comparison, I view what the Yankees are experiencing is in the vein of how I feel about Baltimore and Buffalo. If not now, when? Penn State is this in college football. As for Boston, their NFL comp feels like upstart Washington. I do not know if it is coming now, but maybe soon?
We may soon be living in a world where Aaron Judge retires ringless like Ted Williams or Tony Gwynn.