Yankees Greats Drafted After the Fifth Round

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Throughout Yankees franchise history, some of the best to ever don pinstripes came from the first round of the MLB Draft.

We're talking the likes of Derek Jeter, Aaron Judge, Thurman Munson, even Gerrit Cole, although he didn't sign initially when the Yankees drafted him in 2008.

What about the others that were picked long after the first round? You know, the players that weren't necessarily the highest-rated prospects out of school or those that fell lower than expected on draft day?

In this year's MLB Draft, those players that were been picked after round five would've been on the outside looking in. With the draft truncated to just five rounds, only 160 players were taken this week – that's compared to 1,217 across 40 rounds a year ago.

READ: Breaking Down Yankees' 2020 MLB Draft Class

To honor the ballplayers that didn't get a chance to hear their names called this time around – and those that had to wait until the later rounds to get picked in the past – here are some of the best players to be drafted by New York after round five. 

We'll start with two dynamic arms from the 2006 MLB Draft and work our way back in time from there...

Dellin Betances

2006 – Round 8, 254th overall

From high school in Brooklyn, to the mound in the Bronx. 

Dellin Betances went from the 254th pick in 2006 to one of the best relievers in the game just under a decade later.

Betances finished third in the race for the American League Rookie of the Year in 2014, earning a trip to each of the following four All-Star Games. He's no longer wearing pinstripes – signing with the New York Mets this offseason – but will go down as one of the best Yankee relievers (beyond Mariano Rivera, of course) in franchise history.

David Robertson

2006 – Round 17, 524th overall

Out of the University of Alabama, David Robertson was picked by the Yankees nine rounds after Betances. His path to the big leagues was quicker, debuting just two seasons later. 

Speaking of Mariano Rivera, for a while, Robertson was billed as his replacement. The right-hander saved 39 games for the Yankees in 2014 after shining out of a set up role for much of the previous five seasons. He too is no longer in pinstripes, but over nine yers in the Bronx, Robertson posted a 2.75 ERA with 666 strikeouts in just under 500 innings pitched. 

Marcus Thames

1996 – 30th round, 899th overall

Just a few days ago marked the 18-year anniversary of Marcus Thames' MLB debut – a game in which the slugger homered on the very first pitch he saw ... off Randy Johnson.

The 30th-round pick only ended up playing two years in New York. He spent six seasons with the Tigers, sandwiched between cups of coffee with the Rangers and Dodgers. Over his decade in the Majors, Thames mashed 115 home runs. 

Thames may not be the biggest name on this list, but he gets preferential treatment as the Yankees' hitting coach. It's only fair.

Andy Pettitte

1990 – 22nd round, 577th overall

That's right. Five-time World Series champion Andy Pettitte, one of the best postseason pitchers in baseball history, was a 22nd-rounder. 

Pettitte was taken by the Bombers in 1990 out of high school. Unbeknownst to Yankees fans at the time, the southpaw would join forces with the other members of the Core Four (yes, and Bernie Williams) in New York's farm system, biding their time before their chance to kickstart the Yankees' late-1990s dynasty.

READ: 'The Core Four's Last Dance'; Yankees Version of ESPN's Michael Jordan Miniseries

Over 18 big-league seasons, Pettitte won 256 games – including two 21-win campaigns – and made three All-Star Game appearances. He holds the record for the most wins (19) and innings pitched (276 2/3) ever in postseason play.

Derek Jeter alongside Jorge Posada, Tino Martinez and Andy Pettitte at 2019 Hall of Fame Induction

Jorge Posada

1990 – 24th round, 629th overall

If you thought Pettitte was taken low in 1990, get this. His battery mate Jorge Posada was selected two rounds later. A pitcher named Thomas Wilson was taken by New York in the middle of these two iconic members of the Core Four. Wilson never played a single game in the Yankees' Minor League system.

Not only was Posada taken off the board in the 24th round by the Bombers, but the year prior, he was selected in the 43rd round. The catcher played another year of collegiate ball and ended up with the same organization one summer later.

READ: Joe Girardi Believes Jorge Posada Belongs in the Hall of Fame

Over 17 years with the Yankees, the switch-hitting backstop hit .273/.374/.474 with 275 home runs and 1,065 RBI. He won four World Series titles with the Bombers. 

Fred McGriff

1981 – 9th round, 233rd overall

Hard to follow up the likes of Posada and Pettitte but this all-time great will do the trick. 

Fred McGriff was taken in the 9th round of the 1981 MLB Draft. Before he could make his Major League debut in a Yankees uniform, however, New York dealt him to the Toronto Blue Jays (alongside Dave Collins and Mike Morgan) for Dale Murray and Tom Dodd.

That trade is now known as arguably the worst transaction in Yankees' franchise history because McGriff went on to have a borderline Hall of Fame career. Over 19 big-league seasons, the first baseman hit 493 home runs, compiled 2,490 base hits and posted a 52.6 career WAR. 

Don Mattingly

1979 – 19th round, 493rd overall

Finally, Donny Baseball. 

In retrospect, losing McGriff was tough pill to swallow, but luckily the Yankees had Don Mattingly in his prime at first base to ease the blow. Across 14 seasons in pinstripes, Mattingly had a .307 batting average, tallied 2,153 base knocks, won a batting title (in '84) and won an American League Most Valuable Player Award (in '85).

READ: Don Mattingly Baseball Card Re-Imagined By New York Artists In Topps' 'Eclectic' Project

Mattingly has his No. 23 retired in Yankee Stadiums' Monument Park alongside some of the best ballplayers in Major League history. Looking back, the round in which the names of these all-time greats were called on draft day couldn't have had less significance on their iconic careers.

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For more from Max Goodman, follow him on Twitter @MaxTGoodman. Follow ITP on Twitter @SI_Yankees and Facebook @SIYankees