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Yankees Draft Preview 2016: The 5 best deep draft picks in franchise history

The Derek Jeters of the world get all the hype, but diamonds can be found in the rough.

Adam Hunger-USA TODAY Sports

With the 2016 MLB Draft coming up, the Yankees have the 18th overall pick and are geared to add a pretty good prospect into their system. Just a few seasons down the road though, fans might be looking to one of the later names taken in the draft as a key selection to the farm system. Dustin Fowler was taken down in the 17th round in 2013 but has worked his way into the top 10 with some steady performances up into Double-A.

Perhaps Fowler will one day join this group, the five best Yankees ever taken deep in the draft. To make this list, a player needed to be selected beyond the 10th round and also to have actually had success with the Yankees. Mike Lowell was an incredibly savvy 20th round pick in 1995, but since he flourished in Miami, he does not count. Fortunately, the formerly overlooked prospects here more than make up for Lowell's absence.

5. Doc Medich

Doc Medich Pictorial Parade/Getty Images

Drafted: 1970, 30th round
School: Pittsburgh

Doc Medich is one of the numerous names that have been somewhat forgotten in Yankees history; the fact that his years with the team came just before the team's three consecutive AL pennants from '76-'78 doesn't help. George Medich was nicknamed "Doc" since he continued his studies as a med student at Pitt, though ironically not much ever came of his degree since his medical license was suspended for possessing prescription drugs written to non-existent patients. Medich had an inauspicious MLB debut, giving up two singles, two walks, and two runs to the Orioles. Ralph Houk removed him before he even got an out. His ERA in '72 was infinite.

Medich rebounded to finish third in AL Rookie of the Year voting in '73 with a 2.95 ERA and 3.7 fWAR in 32 starts (235 innings), and he won 19 games in his second full season. After one more fine season in '75, he was shipped out of town, back home with the Pittsburgh Pirates. In return, the Yankees received Ken Brett of George Brett fame, Dock Ellis of LSD no-no fame, and some schmuck second baseman. Medich pitched seven more years with six different teams before his career ended in '82. His Yankee career was short, but we certainly cannot fault the Yanks for trading him considering that the infielder in the deal turned out to be Willie Randolph.

4. David Robertson

David Robertson Rich Schultz/Getty Images

Drafted: 2006, 17th round
School: Alabama

The Yankees' draft strategies have been fairly criticized over the past couple decades, but they can at least solace in their 2006 draft class. That will go down as one of the best franchise history for the sheer volume of pitching. Six of the first seven pitchers taken that year went on to become legitimate major leaguers: Dellin Betances, Ian Kennedy, Mark Melancon, Joba Chamberlain, Zach McAllister, and George Kontos. That would have been a stacked group anyway had it not been for Crimson Tide closer David Robertson.

Despite his late selection, Robertson was fairly close to a major leaguer already. In his minor league debut the next season, he fanned 12.1 batters per nine innings while rocketing from Charleston to Trenton. Robertson joined the Yankees in June 2008, just a little over two years after being drafted. It was great fun watching him rise in the bullpen ranks from unsung '09 mid-relief hero to All-Star setup man and Mariano Rivera's worthy successor by 2014. Although the two sides parted ways the following off-season, Robertson's Yankees career featured a 2.81 ERA, a 2.69 FIP, 39 saves in 2014, and 524 strikeouts in 393 1/3 innings, a 12.0 K/9. That will do.

3. Jorge Posada

Jorge Posada Nick Laham/Getty Images

Drafted: 1990, 24th round
School: Calhoun Community College (Decatur, AL)

When the Yankees drafted Jorge Posada, he was just some scout's son who couldn't play the infield. Thankfully for Posada, he had a natural ability to hit for great power, and hard work behind the plate made him a passable defender. His father's dedicated efforts to make him a switch-hitter really paid off as well. Posada had already proven himself major-league ready by the mid-'90s, but he was stuck behind Joe Girardi on the depth chart for awhile--he did not play more than 112 games in a season until age 28. Posada played a little more than Girardi by '98-'99, and in the 2000s, he took off.

Posada dominated the position for that decade, batting .283/.386/.492 with a 129 OPS+ and five All-Star selections. He finished third in AL MVP voting in '03 thanks to a 146 wRC+ and a career-high 30 bombs, then surprised everyone in '07 with a high-average season at .338/.426/.543 with a 157 wRC+. The Yankees made the playoffs in all but one season--the one they missed was the only one of the 2000s wherein Posada suffered a season-ending injury. It was hardly a coincidence that Posada's absence led to their lone season without October baseball in that stretch. By the time he hung up the spikes in 2011, Posada secured his legacy as yet another in the long line of tremendous Yankee catchers.

2. Don Mattingly

Don Mattingly Jim McIsaac/Getty Images

Drafted: 1979, 19th round
School: Reitz Memorial HS (Evansville, IN)

In hindsight, it is baffling that 492 players were selected before "Donnie Baseball" received the call from the Yankees in the '79 draft. Nonetheless, he slugged his way through the system, never spending more than a year at any level from Low-A to Triple-A, and though the Yankees' first base situation was crowded in the early-'80s, he forced them to put him in the lineup. After bouncing around between the outfield and first base in a fine rookie season in '83, he took the league by storm by beating out Hall of Fame teammate Dave Winfield for the '84 batting crown at .343. That was the beginning of a tremendous six-year run for Mattingly, who hit .327/.372/.530 with 257 doubles and 160 homers and made the All-Star team each season.

Mattingly complemented his potent bat with the best first base defense in the league, and he also won the '85 AL MVP before finishing runner-up to Roger Clemens in '86. That year, he set Yankee records for most hits (238) and most doubles (53). Mattingly looked like a surefire Hall of Famer at age 28, but a quick decline due to nagging back injuries greatly hurt his case and eventually ended his career young six years later. He finally made it to playoffs though, and some still maintain that he should be in Cooperstown. While that is up for debate, his status as one of the great draft steals and the best Yankee first baseman since Lou Gehrig is certainly not.

1. Andy Pettitte

Andy Pettitte Brian Bahr/Getty Images
Drafted: 1990, 22nd round
School: Deer Park HS (Deer Park, TX)

True talent sure was hidden in the late rounds of the '90 draft, though not so much for Tom Wilson (the Yankees draft pick taken between Pettitte and Posada). This soft-spoken lefty from Texas rose from the 22nd round to make Baseball America's Top 100 prospects list by the beginning of the 1995 season and later became the Yankees' best pitcher since Whitey Ford. His excellent career was interrupted only by a three-year stint in Houston when, during free agency, George Steinbrenner didn't feel Pettitte was worth a call, and a brief year-long retirement in 2011. Incredibly, Pettitte only had one season with an ERA- worse than league average--also that 2008 campaign. Otherwise, Pettitte was durable and consistently difficult for hitters to handle.

Pettitte also pitched to a 3.81 ERA in 276 1/3 playoff innings, matching his regular season numbers against the best offenses baseball had to offer since the beginning of the Wild Card era. He won the 2001 ALCS MVP with two terrific starts against the 116-win juggernaut Seattle Mariners, leading to their early five-game demise. Other playoff highlights include a near-shutout in the second game of the '03 World Series, a dominant 7 1/3 inning shutout start to clinch the '98 World Series, clinching wins in each round of the '09 playoffs, and of course his 8 1/3 scoreless innings in a 1-0 victory during fifth game of the '96 World Series in Atlanta. Pettitte is absolutely beloved by Yankees fans, and it's not hard to see why.

Portions of the entries have been reproduced from another draft history post I wrote in June 2013.