World Series: Why star players aren’t the only ones involved in Yankees vs. Dodgers heading for Hall of Fame

The 2024 World Series will commence tonight with Game 1 at Dodger Stadium between the New York Yankees and the Los Angeles Dodgers. The Yankees and Dodgers were not only the top seeds in their respective leagues, but they’re familiar foes: this will mark the 12th World Series between these franchises, with the Yankees prevailing in eight of the first 11. (The Dodgers won the most recent matchup between the two, back in 1981.)

CBS Sports has already previewed the World Series in myriad ways, from breaking down various X-factors that could swing the series to ranking every single player expected to be on the two rosters. One other angle worth hitting involves two future Hall of Famers who won’t take a single at-bat or throw a pitch in this series: Yankees general manager Brian Cashman and Dodgers president of baseball operations Andrew Friedman.

Blame it on “Moneyball,” fantasy baseball, or whatever else, but the general manager has grown into a (or, for some, the) main character over the past couple decades. Tears for Fears sang that everybody wants to rule the world. Maybe then, but these days what everybody wants to do is to generally manage their own baseball team.

With that in mind, let’s highlight the last two top executives standing this fall.

Brian Cashman, GM, Yankees

Cashman is no stranger to this position. That sentiment applies in multiple respects. Foremost, he’s the league’s longest-tenured general manager, having served in his post since 1998. Additionally, he’s been there and done that in the Fall Classic, winning four to date. Should the Yankees prevail here, Cashman would become the first GM with World Series victories across three decades in the 30-team era. (Cashman may argue he was deprived of a fourth in 2017 by the Houston Astros’ sign-stealing.)

Of course, there is no shortage of people quick to undercut Cashman’s success by belaboring the Yankees’ financial might. There’s no denying that being able to afford and simultaneously employ several well-compensated superstars makes the job easier. At the same time, the gig comes with its share of negatives (the pressures to deliver a constant winner chief among them), and Cashman’s Yankees have been among the league’s first movers on several notable innovations (including catcher framing and the sweeper); for a nontrivial chunk of the audience, that’s all they need to know and all they need to say about Cashman. (Friedman has benefitted from a fiscal powerhouse, too, but he ascended leading the Tampa Bay Rays on a shoebox budget.)

It is funny, then, to look at this particular Yankees roster and realize that most of the top contributors were home-grown. If you go off Baseball Reference’s Wins Above Replacement metric, four of the top five performing Yankees made their big-league debuts with the Yankees. (The exception being Juan Soto.) Expand the scope, and only four of the top 12 fit into the star acquisition bin: Soto, Gerrit Cole, Carlos Rodón, and Jazz Chisholm.

Again, that isn’t to suggest Cashman and the Yankees don’t benefit from their ability to run high payrolls; rather, it’s to contextualize that Cashman doesn’t receive enough credit for the larger part of his job: assembling the rest of a pennant-winning roster. 

We often hear from rival front-office executives who argue that their clubs don’t receive the credit from the media that the Rays would if they made the same moves. (Some sources are prone to pointing out the Rays halo effect that sees every prospect they acquire gain immediate public standing.) You can argue the idea if you want, but there’s truth to it. Imagine, for a second, if the Rays had done these things:

• Drafted Aaron Judge, a soon-to-be two-time MVP Award winner, with the 32nd pick in a draft;
• Turned Jake Cave into Luis Gil, and Gil into a starting pitcher with a three-win season under his belt;
• Plucked Nestor Cortes off waivers and helped him not only make an All-Star Game, but develop into a rotation anchor for several years;
• Turned Luke Weaver, a 30-year-old journeyman with a career 5.14 ERA, into an elite reliever.

You get the point. Cashman no doubt has it easier in some ways than most of his peers; that doesn’t mean his deftness should go undocumented.

Andrew Friedman, President of Baseball Ops, Dodgers

The irony of this matchup is that Friedman is the one responsible for the Rays glow-up in the first place — he’s the one who operated the derrick that lifted Tampa Bay’s organization from laughingstock to contender status. Friedman has spent nearly a decade running the Dodgers, turning them into arguably the league’s model franchise.

Perhaps the easiest summation of Friedman is that he combines Billy Beane’s lust for inefficiencies with Dave Dombrowski’s flair for dramatic moves. Friedman’s Dodgers can afford the Shohei Ohtanis, the Yoshinobu Yamamotos, the Mookie Betts, and so on. But he hasn’t lost his ability to identify and obtain the gems that allowed his Tampa Bay teams to ball on a budget. Be it Will Smith or Gavin Stone or Alex Vesia or any number of others. How, exactly, does he do it? There are a few obvious ways.

Friedman once alleged in an interview with the Tampa Bay Times that his favorite book was “The Art of War.” We don’t believe that for a second, but to his credit, he’s mastered the concepts of knowing yourself and remaining flexible.

Part of it is that Friedman’s clubs have long been on the cutting edge. We mentioned that the Yankees were one of the first teams in on catcher framing and the sweeper; Friedman’s clubs were right there, too, if not even leading the charge. He was citing exit velocity to Carlos Peña before it became a talking point. Friedman’s teams have been out in front on the shift, the elevated fastball, the launch-angle swing, the ongoing reversion to the sinker, and so on. They’ve been using novel technology, like force plates, for so long that it’s hardly notable anymore. 

Friedman is also wise enough to fund other parts of the baseball operations department. As one veteran scout told us a summer ago, the Dodgers have a massive player development staff that is capable of creating individualized progression plans. That combination explains why Los Angeles keeps overperforming its draft slot, and why it seems to be the place where afterthought trade acquisitions flourish. (Keep an eye on outfielder Zyhir Hope — he has a real chance to be the next in line.)

If there’s one obvious blemish on Friedman’s legacy it’s that he’s too often found himself doing business with players who have questionable pasts and legal histories. You individually may not care about such things, but to ignore that aspect is to fail to grasp the entirety of his career.

And what of the entirety of Friedman’s career? He’s already won his fifth pennant. A World Series victory would represent his second. He’s around the same age now that the aforementioned Dombrowski was when he took over the Detroit Tigers. In other words, Friedman might still have a few more decades left to write the rest of his story. That’s a scary proposition for the rest of Major League Baseball.