Yankees: 4 Draft Picks New York Couldn't Make Under 2020 Rules

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As the Yankees prepare to mold their future, the 2020 MLB Draft will offer the fulfillment of a lifelong dream to far fewer candidates than ever before.

The draft was once an endlessly sprawling event, replete with 62 rounds of potential selections with treasure at every turn (hello, Pick No. 1,390: Mike Piazza!). The modern iteration had been whittled down to 40 rounds, until the coronavirus pandemic, combined with dissent between MLB and its minor league affiliates, knocked the tradition down to a mere five rounds in 2020.

That’s an entire universe of talent that will be forced to either sign contracts as undrafted free agents, or reenter the pool in 2021.

It’s easy for casual fans to assume that very little talent can be had in the draft’s later rounds, but it’s quite routine to stumble upon cornerstones well after the first five cycles have been completed. In fact, if tragedy had struck in other years, the Yankees never would’ve been able to make these four franchise-altering selections.

New York Yankees reliever David Robertson (Photo by Paul Bereswill/Getty Images) /

The New York Yankees drafted Houdini in the 17th round.

4. David Robertson, 2006 (17th Round)

The moment he refocused himself with the bases loaded and no outs in Game 2 of the 2009 ALDS was the moment David Robertson became an all-caps YANKEE, and it never would’ve happened if he’d been draft eligible in 2020.

Robertson ended up making such an impression in Pinstripes that he was brought back for a return tour of duty midway through the 2017 season after taking his requisite free agent closer contract in Chicago following the 2014 campaign.

His best season, all things considered, was 2011, when D-Rob became the rare non-closer to earn an All-Star selection and serious Cy Young consideration (he finished 11th!), posting an insane 1.08 ERA and 100 Ks in 66.2 innings pitched. His spotless first two rounds of the 2017 postseason also cannot be ignored — save for an aberration late in Game 6 of the ALCS, Robertson was nails for his “new” team, going 4.2 innings and allowing a single hit in a five-game series with Cleveland.

Alas, there won’t be a D-Rob-esque surprise selected by the Yankees this year. They’ll never risk a top-five-round selection on a draft-eligible sophomore with a reliever profile.

Former New York Yankee Jorge Posada admires his plaque. (Photo by Jim McIsaac/Getty Images) /

Jorge Posada wouldn’t have gotten a chance in 2020’s MLB Draft.

3. Jorge Posada, 1990 (24th Round)

The Yankees liked Jorge Posada so much they selected him twice — in two separate rounds that won’t exist this year.

In 1989, they took Posada in the 43rd round out of Calhoun Community College in Decatur, AL. In 1990, they tried again, snagging him in the 24th. And you won’t believe this…it worked!

Though he silently sat around in the clubhouse during the 1995 postseason, a 25-year-old Posada got his first real chance at a backup job in 1997, hitting .250 in 224 plate appearances. His 1998 breakout power surge went under the radar thanks to so many impressive veteran performances that year, but 17 home runs from a complete unknown made him impossible to ignore.

In 2000, a 28-year-old Posada made his first of four consecutive All-Star appearances, cementing himself as perhaps the most unexpected member of the Core Four, and one of the all-time draft steals. And, thanks to the Yankees’ advanced scouting, they first found him in a round that hasn’t existed in decades.

New York Yankees starter Andy Pettitte (Photo by Focus on Sport/Getty Images) /

Andy Pettitte would never have been a Yankee if he’d been eligible for the 2020 MLB Draft.

2. Andy Pettitte, 1990 (22nd Round)

Hey, whoever drafted for the Yankees in 1990 deserves a round of applause! What’s that? They’ve already garnered a ton of accolades for building the sport’s greatest dynasty? Got it.

Even so, netting Andy Pettitte out of Deer Park HS in Texas two rounds before importing another Coresman in Posada earns this team the highest of high marks.

Andrew Eugene Pettitte had a more precipitous rise than Posada; while Georgie was on the bench observing through the ’95 run, Pettitte was living it, going 12-9 with a 4.17 mark as a 23-year-old in his rookie season. The kid was a stunningly finished product for a 22nd-rounder, too, going 10-4 with a 2.20 ERA in 168 innings in his first full season in Greensboro back in 1992.

How is an arm like that still available with such a late pick? A polished lefty with a hellacious pickoff move who’d be big-league ready after four years of minor league seasons…yeah, any team in the game would’ve signed up for that. And this summer, if they find a similar arm, they’ll be able to. All it’ll take is a signature.

Don Mattingly of the New York Yankees celebrates his first playoff berth(GREIG REEKIE/AFP via Getty Images) /

Don Mattingly was one of the New York Yankees’ greatest draft steals ever.

1. Don Mattingly, 1979 (19th Round)

Thank goodness the Yankees sent an advanced scout or two to Reitz Memorial HS in Evansville, IN.

That’s where they found Don Mattingly in 1979, two-thirds of the way through a trio of World Series appearances, but on the precipice of a strange decade in which Mattingly would become emblematic of the team for a generation of title-starved fans.

After a short cameo in 1982, Donnie Baseball was in the Bronx to stay at age 22 in 1983, before really busting out in ’84, hitting .343 with 23 homers, and finishing fifth in the MVP chase. The very next year, Mattingly had ascended an extra level, winning the honors over George Brett by knocking in an obscene 145 runs.

Any baseball fan in 1988 would’ve sworn Mattingly was headed for a Hall of Fame career, but his back betrayed him, making the 1995 postseason the slugger’s swan song, capping a high-peak burst of a career.

The ’80s edition of the Yankees-Red Sox rivalry was captained by Mattingly and Wade Boggs, two players who wouldn’t have been drafted in 2020 (Boggs was a seventh-rounder). Yup, 2020’s going to feature a very strange talent overflow.

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Yankees: 4 Draft Picks New York Couldn’t Make Under 2020 Rules