3 biggest Yankees draft mistakes of the past decade

“The New York Yankees should stop flexing their financial muscles. Instead, they should simply build through the draft.”

OK, tough guy. Yeah, that’d be fun. But a successful franchise is supposed to be built both ways, with shrewd draft selections and a little bit of muscle-flexing when the time is right. Unfortunately, the Yankees have come up short in that first department more often than not.

It’s easy to look around the league and think, “Dang, wish we would’ve had a chance to draft some of these studs. Too bad we never tanked!”

It’s much harder to look around the league and realize some of the game’s young stars could’ve been ours anyway, if we’d only been wiser about our business.

The jury’s still out on a few of New York’s first-round picks from the past decade — oh, and we’re restricting this list to first-rounders or supplemental picks, so it doesn’t get too granular. No need to go screaming and crying about how the Yankees missed on their 12th-rounder and could’ve had a serviceable Scranton Shuttle reliever instead. Wahhhh!

From the past several years alone, we still have hope for Clarke Schmidt (2017), Austin Wells (2020), TJ Sikkema (2020), and, uh, Anthony Volpe (2019). We’re not going to make any sort of sweeping judgments there.

Unfortunately, even while attempting to take a step back and be objective, there are still a few clear misses in this scouting department’s recent history. There are some picks that felt weak at the time and have only gotten weaker as the years have passed. There are some with just … a boatload of talent directly behind them, where the Yankees had six swings at it and still managed to pull a Joey Gallo.

Join us, if you will, on this frustrating dive through drafts past. Luckily, it’s not quite as bad as we thought it was going to be, and there weren’t that many failed selections to sift through, but … it’s still fairly upsetting.

3 biggest Yankees draft busts of the past decade

3. Kyle Holder, 2015

At the time, when the Yanks selected Kyle Holder, he was viewed as a good-field, no-hit shortstop snagged at the back of the first round as the team’s supplement to James Kaprielian, their “crown jewel” who’d been chosen earlier with pick No. 16 (Holder went 30th).

Since then, Holder has become … a good-field, no-hit shortstop who was stolen from the team in the Rule 5 Draft, but has since returned. He’s reached Triple-A. He hit .265 with nine homers at Double-A back in 2019. He’s a minor-league free agent. He started as depth, he’s been depth, and he currently seems to be depth, searching for a new home at age 27 (UPDATE: He signed with the Rockies on Thursday. Cool.). A dull, but necessary, pick for the farm, but probably not someone with a lot of projectability baked in, nor someone who you must have at 30, lest he get swiped from you.

Just so we know … who did the Yankees select Holder over at 30? Clearly, they were focused on position players, so we’re not sure how they missed WORLD SERIES HERO AUSTIN RILEY, who went 41st overall!

It also usually helps when you can keep a selection in the family. Perhaps a prospect’s father is, say, a former Yankee, so you can get the inside track on any insight you might need. That’s why we’re also surprised Brian Cashman wasn’t able to pounce on KE’BRYAN HAYES, son of Charlie, also available at pick 32.

Or, if we’re talking young shortstops, the Orioles got one at pick 36, but he ultimately outgrew the position. Still … Ryan Mountcastle?! We could’ve blocked that? All in all, a pick that felt like the safest of safe options back in 2015 has developed exactly as we expected, and has also been lapped by a few players in his immediate vicinity.

2. Anthony Seigler, 2018

The Yankees’ Great Catching Blitz of 2018 had — and you’re not gonna believe this — some unintended side effects.

At the time, it was funky to watch the team’s 2018 draft room hoarding catchers, considering we had mentally locked Gary Sánchez into the spot for the next decade or so. Come on! 2017 El Gary?! How could you have any doubt about his long-term prospects?

Clearly, the Yanks couldn’t pass up Anthony Seigler with the 23rd overall selection, though. Early reports were he was a superfreak prospect, who pitched and hit in high school, and who would surely hit and defend at the next level. So far, so bad, as Seigler has barely appeared in organized baseball, hitting .219 with four homers in 151 at-bats at High-A Hudson Valley last season. In total, he’s played 95 underwhelming games across three minor-league seasons, losing all of 2020 as well for obvious reasons. The 22-year-old is still just … well, 22, but we haven’t seen any flashes yet, leading to the selection of Austin Wells two years later while the big-league catching options regressed.

Even more curiously, the team backed Seigler up with the selection of Josh Breaux in the very next round, another high school catcher. Breaux has proven to have a lot of swing-and-miss in his game and doesn’t get on base much (.298 OBP last year), but at least he’s found the power tool, rocking 23 home runs in 2021. Having a fringe second-round catcher after your first-round catcher bombed doesn’t salve the pain of missing out on … Triston Casas, though!

The hulking, slugging first baseman will be Boston’s solution to Bobby Dalbec soon enough. Remember, Dalbec was … pretty good! But not elite. And everything in Boston has to be elite. Dalbec would’ve been the Yankees’, like, fourth-best hitter last year, and he’s already on his way out. Pretty chill!

While Bobby D was playing the Monster, Casas spent 2021 starring for Team USA at the Olympics and qualifying events, destroying 14 long home runs in the minors, and OBPing .394. Why don’t the Yankees ever seem to target absolute offensive beasts? Why are we always sitting pretty with the Holders and Seiglers of the world while Casas is just hanging out there and moping around?

Again, these guys were clearly available! And only our rivals had the foresight to snag them. Serves us right.