Don’t be surprised Yankee fans…

There’s been much speculation since the season ended about what Yankees’ GM Brian Cashman is going to do to fill the holes, both large and medium-sized, on the Yankees’ roster. With the assumption that Principal Owner Hal Steinbrenner may be willing to relax the purse strings somewhat, many fans are hoping to see a big-time signing or three that would put the Yankees in the “serious title contender” category. Seager, Correa, Rizzo, Freeman, Verlander, and Ray have been names bandied about over the past week and a half.

But I wouldn’t be surprised if the Yankees did this: Use their exceptionally deep farm system to make trades for roster hole-filling star players first.

As I wrote earlier this season, just the shortstop position alone is comically deep among the Yankees minor league teams. For some perspective, shortstop Trey Sweeney was a first-round pick for the team, and he just posted a 133 wRC+ with a .357/.518 OBP/SLG line and a 14% walk rate in A ball – and you never hear his name mentioned because of the talent ahead of him at that position. Everybody knows how highly regarded Jasson Dominguez is as a center fielder but let’s not forget center fielders Everson Pereira and Brandon Lockridge, who both came into 2021 with promise and both obliterated the baseball in high A and AA respectively this season. (Oh, by the way, Estevan Florial is only 23 years old as well.)

It’s no secret across MLB that Oakland will listen to offers for their All-Star first baseman Matt Olson. As GM David Forst recently came out publicly to say that Oakland has no money and re-tooling is their only option. (Which of course, is colossal BS, and also makes it laughable that there are still fans who think it’s Billy Beane’s fault the As haven’t won a World Series this century.) Olson is 27 years old and isn’t eligible for free agency for two more seasons. And in case you weren’t aware of how good Olson is, let me remind you:

He’s played in three full seasons and has improved in each one both offensively and in overall WAR (and he was pretty good to begin with). In 2021, he had both more WAR and a higher OPS+ than Freddie Freeman, Pete Alonso, Max Muncy, Joey Votto, Yuli Gurriel, Jose Abreu, and Anthony Rizzo – only Vlad Jr. topped Olson in both WAR and OPS+ among first baseman in 2021, and Paul Goldschmidt was the only other first baseman to top Olson’s WAR besides Vlad. And if one season is too small of a sample size, going back to 2018, only Freeman and Goldschmidt have accumulated more WAR than Olson since then.

Oh, and by the way: In addition to being a plus fielder, Olson has hit 89 home runs since 2019. It would have been 101 if his at-bats were in Yankee Stadium.

It’s hard to believe that only six years ago the Pirates won 98 games and made the postseason for the third year in a row. But they’ve been awful since and they may say they’re not willing to talk about center fielder Bryan Reynolds, but it’s the Pirates, so let’s talk.

Similar to Olson, not only was the 26-year-old Reynolds (who has four more seasons before free agency) a monster last season but he also improved in his second full season, and his first one was pretty damn good. Reynolds led all MLB centerfielders in both WAR and OPS+ in 2021 in addition to ranking in the 96^th percentile in MLB in Outs Above Average. For what it’s worth, he’s also a switch hitter with a sprint speed ranking in the 88^th percentile. (I might be reaching, but I think the Yankees could use someone with that skillset…)

Parting with significant prospects is never something you like doing, but if you can get a proven star in exchange it’s worth the risk far more often than not. Particularly when the Yankees have depth from which to deal in the farm system (so if not now, when?) and both Olson and Reynolds come cheap, assuaging any of Hal’s concerns about turning into his father. That’ll give the Yankees even more flexibility to open the checkbook for a shortstop.