Yankees Draft: Biggest First Round MLB Draft Busts

The New York Yankees’ draft history includes some legendary MLB Draft busts.

Good news: the New York Yankees draft history includes some absolute steals, like Andy Pettitte and Jorge Posada, who built the foundations of dynasties.

Bad news: Many of their first-round picks are completely abhorrent. Sometimes, they don’t even make them. Ever wonder why the ’80s featured so many bloated, aging stars? New York only made two first-round picks in the entire decade. Their names were Jeff Pries (’84) and Anthony Balabon (’85). They weren’t very good.

With MLB Draft night (Five-Rounds-Only Edition) finally upon us, it’s time to look in the mirror and try not to get spooked by what looks back, Yankee fans. These are the biggest first-round busts in our franchise’s history.

Author’s Note: If injuries were the sole reason for your downfall, you don’t make my list. Sorry! Writer’s choice. Ty Hensley, your story is sad, and you don’t belong here. Best of luck to you.

5. Yankees Draft: CJ Henry

CJ Henry was the Yankees’ first-round draft pick in 2005, and he didn’t make it in MLB.

With the 17th overall selection in the 2005 MLB Draft, the New York Yankees selected shortstop CJ Henry out of Putnam City High School in Oklahoma City.

At the time, this was a big deal.

An athletic shortstop? With Derek Jeter still in his prime? At pick No. 17?! They don’t usually select that high!

Turns out, New York didn’t have any plans for Henry beyond the very next season. He hit .240 at Single-A Charleston with a pair of homers in his first full season in the system in 2006…before serving as the centerpiece of the Bobby Abreu trade with the Philadelphia Phillies. What a heist!

By 2008, Henry was somehow back in the Yankees system, wrapping up his career with Single-A Tampa. By 2010, he was…playing basketball for the Kansas Jayhawks.

Henry’s bust potential is downgraded only because he netted the Yankees a legitimate star for 2.5 years. Other than that, he was catastrophic at 17 — and, if the Yanks had drafted smarter, they could’ve had Jacoby Ellsbury (No. 23) on his rookie deal instead of his bloated one.

4. Yankees Draft: David Parrish

Yankees draft bust David Parrish was not the catcher of the future.

Drafting a Michigan man in the year 2000 is supposed to result in six rings, not total bust status. Unfortunately, only one franchise gets the chance to luck into Tom Brady.

The mid-dynasty Yanks opted for Jorge Posada’s replacement in David Parrish (a bizarre decision at that juncture, anyway), and got burned yet again.

This bust gets upgraded in severity because the Yanks opted for Parrish not once, but twice — the team also selected the catcher in the 10th round out of high school in 1997, before selecting him at the end of the first in 2000.

Parrish toiled in the minors for nine seasons and a devilish 666 games, hitting 35 total home runs, and never rising above the level of “potential third-string catcher” with the big club. If the Yankees had spent an extra few hours scouting that year, they could’ve chosen…Adam Wainwright, exactly ONE pick later. The Yankees may have been the Team of the ’90s, but the Braves got their goat when the new millennium began.

3. Yankees Draft: David Walling

The New York Yankees draft guidebook didn’t seem to include pitchers in ’99-’00.

We’re not sure who was in charge of scouting pitchers for the Yankees at the end of the 1990s and the turn of the next decade, but whoever it was: A) found almost no one and B) drafted literally Brandon Weeden (2002).

Stuck in the doldrums at the end of the first round yet again in 1999 (winning the World Series STINKS!), the Yankees selected righty David Walling out of the University of Arkansas. Unfortunately, the “Woo Pig Sooie!” in this case represents a reaction to the offensive smell of Walling’s baseball career, and not a hopeful war cry.

In 2000, Walling dominated the Single-A level, going 7-2 with a 1.98 ERA. Unfortunately, he was then promoted to Double-A, where everything went off the rails (3-9, 5.29 ERA). After struggling for the first time…ever, Walling developed a compulsion, throwing to first an abnormal amount of times per start. A sports psychologist was called in to save his career, but it didn’t work — Walling walked away in 2002.

Luckily for the Yanks, the rest of the 1999 draft…was also bad! The most realistic options the Yankees passed on were Colby Lewis and Brian Roberts.

1. Yankees Draft: Brien Taylor

Brien Taylor could’ve been a part of the 1990s Yankees Dynasty. He wasn’t.

I know this sounds unfathomable, but bear with me here: the New York Yankees had the first overall pick in 1991. That’s what you get for being 67-95 during a period in time where the top selection switched leagues every year — the Braves got Chipper Jones in 1990, the Yankees got Brien Taylor in ’91. And, as high school pitchers go, he was a sure thing.

At the age of 20, Taylor whiffed 187 men in 161.1 innings at High-A Tampa, posting a 2.57 ERA. At Double-A Albany-Colonie in 1993, he went 13-7 with a 3.48 mark. That’s when the trouble started — I avoided saying “disaster struck” because it was, in fact, Taylor himself who did the striking.

His brother Brenden got in an altercation with a man named Ron Wilson that offseason. When Taylor found out, he stomped to Wilson’s trailer to defend his brother’s honor and began to throw down with Wilson’s friend Jamie Morris. During the ensuing fight, Taylor fell on his shoulder, attempted to deliver a wicked punch, missed, and destroyed the interior of his body. Surgeon Frank Jobe called the injury “one of the worst he’d seen.” After whiffing so many men himself in a two-year minor league tenure, a whiff of Taylor’s own effectively ended his career.

His numbers in his “comeback” season in 1995? 0-5, 18.73 ERA. It was all over.

While failed prospects like Ty Hensley avoided being placed here because their bodies betrayed them, Taylor did it to himself. Depressing, but true — he’s the caveat.