Four-time New York Yankees World Series champion Bernie Williams sat down with FanSided's Adam Weinrib on behalf of the Tune In To Lung Health campaign ahead of Rare Disease Day on Friday, Feb. 28. Visit TuneInToLungHealth.com to learn more about interstitial lung disease, and how Bernie used music to process the trauma of his father's diagnosis (along with a curated playlist).
For all the talk of parity-destroying behemoth spending, no MLB team has repeated as World Series champions for 24 Octobers and counting, leaving Bernie Williams' 1998-2000 Yankees as the last group to do so.
That might not be a point of pride much longer, though; after defeating the 2024 edition of the Yankees in the Fall Classic, the '25 Dodgers reloaded to an almost unfathomable degree, importing Roki Sasaki, Blake Snell, Tanner Scott, Kirby Yates, Hyeseong Kim and Michael Conforto in free agency while also re-signing Clayton Kershaw, Teoscar Hernández and Kiké Hernández. In essence, they left no stone untouched in their attempt to repeat, both collecting other teams' stars like infinity stones and taking care of their own.
Williams has plenty of experience with being scorned for playing in the biggest of games while carrying the biggest of targets. Under George Steinbrenner's watch, the 1990s Yankees became the "something must be done about this" team of the moment, consistently topping the league in payroll and making no apologies about it. In the four-time champion's estimation, though, the Yankees went about financially reinforcing their roster differently than the current Dodgers.
Four-time New York Yankees World Series champion Bernie Williams thinks New York used their financial advantage differently than Dodgers do
"The Yankees of the '90s spent in a way where they wanted to keep their core players with the team," Williams noted. "The spending that way was more positive. You know you're gonna become a free agent, you have this six-year tenure with the team, and now you're looking into other possibilities, so we're gonna make it so you want to spend the rest of your career here."
"Exploring other possibilities" is something Williams knows well; raised in the Yankees farm system, he happily returned after nearly defecting to Boston in 1999 once Steinbrenner and Brian Cashman found a satisfying number. New York in the '90s used their financial might to make sure their core stayed together; the 1998-2000 team mostly subsisted on standout contributions 1-through-9 rather than breaking the bank to bring in superstars. Once they started doing that, in fact, things spiraled slightly (see: Alex Rodriguez, 2004). Even Roger Clemens, the glitziest name of the dynasty era, came via trade (and cost a fan favorite in David Wells).
The Dodgers, on the other hand, are operating in a way that's earned them understandable scorn, in Williams' eyes.
"Assembling a team of different parts from different organizations ... it may look good on paper, but there's something to be said about chemistry," Williams continued. "Getting that sort of cohesiveness on a team, that only happens a few times ... I think that might be the thing that might be a little bit different with the Dodgers. But I think they're doing it the right way. They're doing it very carefully."
While it may feel slightly inorganic compared to the relentless roster he was raised on from the farm system up, Williams will never begrudge any franchise for doing whatever it takes to scale the mountaintop in back-to-back seasons.
"I will never criticize a team for trying to repeat. I knew that, when I was playing, that was probably the hardest thing and the least rewarding thing you could do," Williams said, expressing exactly what fans have long assumed to be true. "People get tired of seeing you. The Chiefs, going to the Super Bowl every year! You love to be hated, but for a team player, that's probably one of the hardest things to do. You have everything to lose and not a lot of things to gain."
"If you win, oh, it was expected. But if you lose, you lose big."