With the amateur draft signing deadline having just passed, I want to spend a couple of entries here looking at the Yankees’ farm system with an eye towards a very specific problem, the absence of solid outfield prospects. The Yankees don’t have them and haven’t developed one in a very long time. While Melky Cabrera and Brett Gardner have their uses, the last outfielder to emerge from the farm system and have anything like a substantial, above-average career with the Yankees was Bernie Williams.

This puts immense pressure on them to retain an aging Johnny Damon this offseason whether giving him another contract is a good idea or not. This is the same pressure that led to the decision to sign Carl Pavano and Jaret Wright a few winters ago when the farm system could not render up quality pitchers. That problem has been treated to a large extent, but the absence of quality position players continues to impel the Yankees towards free agent adventurism.

Since the great center fielder/guitarist, numerous outfielders have passed through the system on their way to the Bronx without making a lasting impression. The parade includes Gerald Williams, Shane Spencer, Ricky Ledee, Ruben Rivera, Kevin Thompson, Justin Christian, Kevin Reese, Shelley Duncan, Donzell McDonald and even Mike Vento. The best of the lot were Marcus Thames, who was dealt away to the Rangers for the mortal remains of Ruben Sierra in 2003, and Juan Rivera, a strong hitter with a tendency towards injuries. He too was traded in 2003, to the Expos as part of the package for Javier Vazquez.

What is meant by a “solid” outfield prospect? It’s a young player who might hit even five percent better than the league average at his position. That’s not asking for the moon or Joe DiMaggio. Five percent better than a Major League average left fielder would be .282/.358/.460; for a center fielder it would be .281/.353/.441; for a right fielder, .284/.362/.465. This is asking for a good player, not a great one. Don’t take those numbers too seriously — they’re just broad guideposts for a hypothetical player who might hit for more power or take fewer walks while arriving at roughly the same place. Whatever your definition of “slightly above-average outfield starter,” that is what is being aimed at.

Prior to the season, Baseball America compiled their list of the top 100 prospects in baseball and placed two Yankees position players on it, Austin Jackson (No. 36) and Jesus Montero (No. 38). Considering Yankees prospects exclusively, they ranked the top 30 players in the organization and found only 10 position players worthy of ranking that high. Among these were four outfielders: Jackson, Kelvin DeLeon, Abraham Almonte and Gardner.

Kevin Goldstein of Baseball Prospectus also compiled a top 100 prospects. As with Baseball America, Jackson (No. 46) was the only Yankees outfielder to rank among the elite prospects in the game. Goldstein also compiles rankings of each organizations top 11 prospects, plus honorable mentions. Using those lists, I compiled the top 86 prospective outfielders coming into the season. Just two of the 86, Jackson and DeLeon, belong to the Yankees.

Although Goldstein’s lists of 11 are more restrictive than BA’s top 30, the shorter list ensures that we are examining players who have a chance to start, as opposed to the likely reserves who often fill out BA’s lists for thinner organizations. Almonte may be the 30th-best prospect in the Yankees organization, but given his current offensive profile (“current” because he is quite young and could evolve) his chances of starting for the Yankees or any team is nil.

Thus, 84 of 86 top outfield prospects coming into the season belong to other organizations. The purpose is not to second guess — as you will see, some of the best of these prospects were early first-round picks, and thus unavailable to the Yankees due to the nature of their consistent high finishes, and it would be unfair to criticize them for that — but to ask what priorities and assumptions the Yankees were working off of in the draft, and to see if other teams are doing a better job of finding outfield prospects in the later rounds or on the international talent market, where good scouting and luck play a greater part.

If the Yankees are stumbling into fewer of those “solid” non-star starters than would be expected, be it because of organizational priorities or simply poor choices, we’ll see why as we explore the top 86 and where they were selected in the draft.

First Round (13): Colby Rasmus (2005/HS), Cameron Maybin (2005/HS), Andrew McCutchen (2005/HS), Brian Bogusevic (2005/C), Trevor Crow (2005/C)Travis Snider (2006/HS), Drew Stubbs (2006/C), Tyler Colvin (2006/C), Jason Heyward (2007/HS), Matt LaPorta (2007/C), Ben Revere (2007/HS), Wendell Fairley (2007/HS), Aaron Hicks (2008/HS).

What the Yankees did: These players were selected in the 2005 through 2008 drafts, so we’ll look at what the Yankees did in those drafts. In 2005, the Yankees picked at No. 17 thanks to the Phillies signing away Jon Lieber. Their own pick at No. 29 went to the Marlins because they signed Carl Pavano. By the time the Yankees picked, Maybin (No. 10), McCutchen (No. 11), and Crowe (No. 14) were off the board, as was Jay Bruce (No. 12). The Yankees spent their pick on the miserable high school shortstop C.J. Henry. Subsequently, John Mayberry (No. 19), Jacoby Ellsbury (No. 23), Bogusevic (No. 24), and Rasmus (No. 28) were selected.

In 2006, the Yankees gave up their first-round pick (No. 28) to the Red Sox to sign Damon, but for the second year in a row the Phillies handed them their own pick to sign a Yankee who wouldn’t help them much, Tom Gordon. By the time they picked at No. 21, Drew Stubbs had gone to the Red at No. 8, as had Colvin (No. 13) and Snider (No. 14). Another strong hitter, Chris Marrero, went to the Nationals at No. 15 (he was later shifted to first base). The Yankees selected Ian Kennedy. Two other outfielders went in the first 30 picks, Cody Johnson to the Braves at No. 24 (he appears to have potential in a Steve Balboni kind of way), and Jason Place to the Red Sox at No. 27.

In 2007, the Yankees picked 30th, last in the first round. Jason Heyward, who might be the best hitting prospect in baseball just now, was selected from the planet Krypton at No. 14. Ichiro-type Ben Revere went at No. 28, and the Giants took Fairley at No. 29, setting up the Yankees to shock the nation by selecting Andrew Brackman, the less said of whom the better. We’ll look at who was still on the board in the ’07 supplemental and second round when we get to the supplemental picks.

In the Year of Our Draft 2008, the Yankees picked at No. 28. Naturally, a lot of the interesting guys were gone. Even the Yankees’ own interesting guy was gone because they didn’t sign their pick, pitcher Gerrit Cole. Hicks was the only outfielder selected in the first round. He went to the Twins at No. 14.

These last four drafts have been borderline disastrous for the Yankees insofar as the first round, where the sure things are supposedly to be found. They completely missed on Henry, and only the recklessness of the Phillies allowed them to redeem the pick by taking him in return for Bobby Abreu, but it’s clear that if the Phillies took Henry they would have taken anybody — the move was the Alex Rios salary dump of 2006.

Brackman also appears to be a complete miss, but it’s too early to write him off despite the 6.56 ERA and seven walks per nine innings in the Sally League. The failure to sign Cole got the Yankees
an extra pick in the 2009 draft, but there’s still an empty spot in the organization where a player with one year of experience would have been.

Only Kennedy has rewarded the Yankees’ evaluation of him as a prospect, at least until his blood clot surgery this year. That, at least, is an act of God, not scouting. What rankles is the availability of Rasmus, now a rookie center fielder for the Cardinals, in 2005, not to mention Ellsbury, Matt Garza, and Joey Devine, all first-round selections after the Yankees took Henry. Perhaps there were extenuating circumstances, such as Georgia boy Rasmus indicating he would not be happy in the big city, but the same cannot be said of the other players available at that spot.

First Round, Supplemental: Michael Burgess (2007/HS), Kellen Kulbacki (2007/C), Corey Brown (2007/C), Julio Borbon (2007/C), Zach Collier (2008/HS), Jaff Decker (2008/HS).

What the Yankees did: The Yankees didn’t have a supplemental pick in 2007, so they got to watch as Burgess, Kulbacki, Brown, and Borbon (now playing well in the Majors) were selected. In 2008, the Yankees did get a supplemental first-rounder due to the Rockies signing Luis Vizcaino. It was the 14th of the round, two from the bottom, and Collier and Decker had already disappeared by the time they picked. They used the pick on Stanford lefty Jeremy Bleich, now pitching at Double-A Trenton. Note below that a number of quality outfield prospects were available at this point, as several were selected early in the second round.

Second Round: Seth Smith, (2004/C), Nolan Reimold (2005/C), Jon Jay (2006/C), Mike Stanton (2007/HS), Charles Blackmon (2008/C), Cutter Dykstra (2008/HS), Destin Hood (2008/HS), Xavier Avery (2008/HS), Dennis Raben (2008/C), Kenny Wilson (2008/HS), Jay Austin (2008/C).

Now things get interesting, because any of these players were available at the time that the Yankees picked at the end of the first round. In 2005, the Yankees picked at No. 15 in the second round thanks to the White Sox signing Orlando Hernandez (there should probably be an axiom in baseball that says that if the Yankees don’t feel like spending the money to retain their own free agent player, that player is probably not worth having). Their own second round pick (No. 29) went to the Braves due to the ill-considered signing of Jaret Wright. The Orioles took current rookie Reimold two picks ahead of the Yankees, who selected reliever J.B. Cox, now pitching at Trenton.

The Yankees had no second-round pick in 2006 because their pick went to the Braves as compensation for Kyle Farnsworth, which is depressing. Cardinals center field prospect Jay would have been available to them. The Yankees had the last pick of the round in 2007. They made a solid pick in catcher Austin Romine, currently batting .277/.319/.445 for High-A Tampa. The Yankees picked 29th in round two, 2008. They went with Ole Miss righty Scott Bittle, who they elected not to sign. As we will see momentarily, this meant passing on a couple of quality outfield prospects who would be selected in the third round.

We’ll pick up with the third round in our next entry.