Top 5 Yankees Draft Picks in Rounds 1-5 of All Time

Lou DiPietro
June 02, 2020 - 9:20 am

The 2020 MLB Draft will be an unusual one, as the league’s annual Rule 4 Selection Meeting will include only five rounds and 160 total selections, including all Competitive Balance and compensation picks – a mere fraction of the 40 rounds and 1,217 selections that were made in 2019.

The shortening of the draft also means that undrafted talent will be at a premium, so there may be quite a few players in the future whose paths mirror that of Mike Ford, who went undrafted out of Princeton in 2013, but there will be no contemporaries for fellow Class of 2013 Yankees like Chad Green (Tigers’ 11th-rounder in 2013) or Luke Voit (Cardinals’ 22nd-rounder in 2013).

The Yankees only have three selections, having forfeited their second- and fifth-rounders to sign Gerrit Cole, but the choices they do make will hope to live up to the legacies left by these men: the team’s best picks ever made in the first five rounds, according to WAR.

ROUND 1: Derek Jeter (No. 6 overall selection in 1992, 71.3 WAR)

Listen, this one is pretty obvious, and every Yankees fan surely knows how, almost 28 years ago, scout Dick Groch spoke up about the future of infield prospect Derek Jeter and his commitment to Michigan by saying, “the only place he’s going is Cooperstown.”

COVID-19 had other ideas for this year’s Hall of Fame enshrinement, but Jeter made Mr. Groch’s prophecy a reality this past winter, falling just one vote short of being the second unanimous Hall selection in history. Outside of The Captain, though, the Yankees’ storied history is mostly bereft of first-round draft success, with only 10 of their 58 first-round picks since the start of the common draft era in 1965 accruing a double-digit WAR total – and five of those 10 (including Gerrit Cole, at least until baseball resumes) have never played a single major-league inning in pinstripes.

Of those who did, the honorable mentions are Thurman Munson (46.0), Aaron Judge (19.1 and counting), Ian Kennedy (17.6), and Phil Hughes (11.0). And, to be fair, Cole is now a Yankee, Carl Everett was lost in the 1992 Expansion Draft, Eric Milton and Scot McGregor were dealt for key pieces of some World Series teams, and Mark Prior did eventually spend time in the Yankees’ system in 2011.

ROUND 2: Al Leiter (No. 50 overall selection in 1984, 40.0 WAR)

The crafty lefty may have spent more time in Yankee Stadium in the broadcast booth than in the dugout – and definitely spent more time in New York as a Met than a Yankee – but Leiter began and ended his MLB career in the Bronx, amassing an 11-13 record and 5.17 ERA in 169 innings in pinstripes.

Leiter and catcher Mike Heath, who was selected in 1973 and debuted as part of the 1978 championship team before being dealt to Texas for Dave Righetti among others, are the only Yankees second-rounders to amass double-digit WAR. Third on the list is Bo Jackson, whose first of three draft selections came from The Bronx in 1982,

Fun fact: the only Yankees second-round picks to either play 162 games or pitch 162 innings in pinstripes are Leiter (barely), Steve Balboni, and Austin Romine, and the latter two have a combined career WAR (so far) of 0.8.

ROUND 3: Fred Lynn (No. 60 overall selection in 1970, 50.2 WAR)

The third round is an exercise in how narrowing criteria can produce undesired results, as the Yankees’ best pick in this round is Lynn, who was selected out of high school in 1970 and went on to become a nine-time All-Star and the first of only three players to ever win both Rookie of the Year and either MVP or Cy Young in their freshman season.

Of course, he earned those accolades with the Red Sox and Angels, and also spent time in Baltimore, Detroit, and San Diego over a 17-year career that included exactly zero minutes with the Yankees, as he decided to go to USC in 1970 and was later a second-round pick of the Red Sox in 1973.

Second and third on the list, though, are two popular career pinstripers, with Ron Guidry at 47.8 and Brett Gardner at 42.3. Gardy is going to need a couple of big seasons to surpass Lynn or even Guidry, but the longest-tenured Yankee is safely ahead of Nick Johnson (14.5) and Dan Pasqua (10.7).

ROUND 4: Stan Bahnsen (No. 68 overall in 1965, 22.7 WAR)

Bahnsen is the leader of six Yankees fourth-rounders to amass at least a 1.0 career WAR, and he had arguably his career season right off the bat, going 17-12 with a 2.05 ERA in 267 1/3 innings en route to the AL Rookie of the Year Award in 1968. He spent three more years in pinstripes, but accrued most of his WAR in five other MLB stops over a 16-year career.

The rest of that half-dozen is a mix between cups and pots of coffee: Jim Beattie (1975) debuted on the Yankees’ 1978 title team and spent 1979 in pinstripes before being dealt to Seattle; Tim Lollar (1978) debuted in 1980 and was traded to San Diego on the eve of the 1981 season; Adam Warren (2009) has spent most of his career as a Yankee, but was traded twice at the deadline and is now in his third stint in the organization; and Jordan Montgomery (2014) is already in the top six after only 37 appearances.

Oh, and then there’s Eric Plunk (1981), whose claim to fame is that he was twice traded for Rickey Henderson; the Yankees sent him to Oakland in 1984 to get Rickey, then got him back in 1989 when they shipped Rickey back to Oakland. That time, at least, they kept him for two-plus seasons before cutting Plunk after the 1991 season, and he went on to play nine more seasons with the Indians and Brewers.

ROUND 5: B.J. Surhoff (No. 128 overall selection in 1982, 34.4 WAR)

In Yankees history, six fifth-round picks have finished with double-digit WAR totals, and that group has a 119.87 combined WAR in more than 7,500 games played/pitched – and only seven of those games came in pinstripes. The leader of that group that didn’t earn their pinstripes is Surhoff, a high school kid from Rye who spurned the Yankees in 1982 to go to North Carolina instead; it seems he made the right choice for himself, as he was the No. 1 overall pick in 1985, and spent 19 years with the Brewers, Orioles, and Braves, but that’s not exactly comforting to anyone in New York.

After Surhoff, the next four are Greg Gagne (drafted in 1979, dealt to Minnesota in 1982), Todd Stottlemyre (did not sign in 1983), Willie Upshaw (drafted in 1975, taken by Toronto in the Rule 5 Draft in 1977), and LaMarr Hoyt (taken in 1973, dealt to the White Sox for Bucky Dent in 1977) before we get to J.T. Snow, the Yankees’ fifth-rounder in 1989 who debuted as a September call-up in 1992 but was dealt to the Angels for Jim Abbott that December.

Hey, at least the fifth-round helped produce one of the biggest home runs in franchise history as well as a memorable no-hitter, right?