On Sunday, the Yankees are set to select at No. 20 overall in the 2021 MLB Draft. It is a first-round pick whom they hope will be a future star, but we all know it doesn’t always turn out that way.
The Yankees, compared to other teams, haven’t been the best drafters when it comes to first-round talent. Yes, they’ve had some Hall-of-Famers, but when you look at their history, there are too many players you haven’t heard of.
In the end, there are players — impactful ones — who can be appreciated as solid major leaguers. So we’ve decided to rank the five best first-rounders the Yankees have chosen.
Some criteria first: It doesn’t matter if the draft pick ended up playing somewhere else other than with the Bombers. A good pick is still that, even away from New York. Also, injuries and other circumstances do come into play. Some players end up on Hall of Fame tracks but get cut short for whatever the reason may be.
So, with that in mind, let’s start with No. 5, a familiar face to Yankees fans today…
5) Joba Chamberlain (No. 41 overall, Compensation-A pick in 2006)
The Yankees decided to take another pitcher in Chamberlain after going with Ian Kennedy at No. 21 overall in the first round. The 6-foot-2, 230 pounder threw gas coming out of the University of Nebraska-Lincoln.
He quickly got his shot in the bigs that next year, and he owned the spotlight with a 0.38 ERA in 19 games (24 innings pitched). In that short span, he still notched 34 strikeouts. He remained in a relief role in 2008 with a 2.60 ERA, but the Yankees made him a starter in 2009. They’d win a World Series, but learned after he posted a 4.75 ERA that Chamberlain was best in the bullpen.
That’s where he stayed the rest of his career. He was a solid set-up man who would eventually find his way to the Tigers, Royals and then Indians before calling it quits in 2016 at only 30 years old. It was a fast rise for Chamberlain, but it wasn’t as long a career as many believed he would have.
4) Scott McGregor (No. 14 overall in 1972)
Coming out of El Segundo High School in California, McGregor played alongside George Brett but it wasn’t his bat or outfield prowess that caught the eye of the Yankees. It was his pitching ability as a left-hander.
McGregor, though, would never play a lick of baseball in pinstripes. Instead, he was dealt away in 1976 to the Orioles as part of a 10-player trade. And that would be his home for his 13-year MLB career.
He owned a career 3.99 ERA with 138 wins and 2,140.2 innings pitched for Baltimore. He made one All-Star team in 1981 after posting a 3.26 ERA with a 13-5 record. He also had a 20-win season in 1980, and is a World Series champion from his 1983 season.
Pitching over 200 innings in six of those seasons, McGregor was a very consistent rotation piece for the O’s throughout his career.
3) Aaron Judge (No. 32 overall, Competitive Balance Round 1 pick in 2013)
The Yankees had three first-round picks in the 2013 draft — their normal pick at No. 26 overall and the No. 32 and No. 33 picks as well. In that second pick of Judge they found the next face of their franchise.
Judge became the AL Rookie of the Year in 2017 after blasting 52 homers (setting a new rookie record at the time before Pete Alonso broke it in 2019) and posting a .284/.422/.627 triple slash. Injuries made him miss a chunk of time in the three seasons after, but Judge has still proven to be a menace at the plate as well as a solid right fielder with an absolute cannon for an arm.
At 6-foot-7, 282 pounds, there is some concern that Judge’s injury issues will be continuous throughout his career, and may even cut it short at some point. For now, though, he is projecting to be one of the organization’s best first-rounders — as long as he can stay on the field.
2) Thurman Munson (No. 4 overall in 1968)
The Yankees just had a feeling they found the right man out of Kent State when they selected Munson, and they were right. In 1970, he was named the AL Rookie of the Year with a .302/.386/.415 line with 53 RBI, 25 doubles and six homers. And production like that would continue.
He would eventually become a seven-time All-Star and a true leader on the Yankees. It was only fitting that he was named captain for the first time since Lou Gehrig before the 1976 season began. And of course he won the AL MVP that year, too.
Munson won two World Series with the Yanks as well, in 1977 and 1978. He was a career .357 hitter in the postseason with three homers and 22 RBI in 30 games.
Unfortunately, Munson’s career was tragically cut short as he died in a plane crash while practicing his landing at Akron-Canton Airport. It was on Aug. 2, 1979 — the summer after winning the World Series — and he was only 32 years old.
The Yankees would honor Munson immediately by retiring his No. 15 jersey in Monument Park.
1) Derek Jeter (No. 6 overall in 1992)
There were 14 others who held the title before him, but he was nicknamed “The Captain” for a reason.
Coming out of Kalamazoo High School in Michigan, Jeter was a sure first-rounder. He had the perfect makeup for a shortstop and absolutely raked during his time playing high school ball. Though he had his struggles in the minors, Jeter worked his way up to the Yankees in 1995 when he made his debut against the Mariners. He went 0-for-5, though.
That next day, Jeter went 2-for-3 with a walk, and the rest from there is truly history. He would win Rookie of the Year in 1996, and also collect his first of five World Series rings. He was a 14-time All-Star, as he quickly gained fame among the Bronx faithful and those around the league.
Jeter was also a five-time Gold Glove and Silver Slugger recipient as well as a World Series and All-Star Game MVP. There are so many iconic moments, from “The Flip” against the A’s or his “Mr. November” walk-off against the Diamondbacks that it’s hard to keep track.
And that all led to his easily voted into the Hall of Fame. Jeter’s No. 2 is also retired by the Yankees, making it the final single digit to be placed in Monument Park. Jeter was not only a Yankee icon, but one of the best to ever do it at his position through the history of the league.
So, yes, the Yankees definitely got this one right.