"It's always a challenge," Oppenheimer said. "I think if you talk to the guys over there at the Rays, they're probably agonizing over their decision at No. 1 on who their guy is going to be. We all have our tough decisions to make. We're always in the position where we're at the will of whatever goes before us."
Because their board is so readily open to change, the Yankees place a high emphasis on their meetings with area scouts, as well as watching video and holding discussions to have a final blueprint lined up by the time the first name is called.
This year is no different, as the organization's homework will be of the essence. New York also obtained the 43rd selection, in Compensation Round A, from the Colorado Rockies over the offseason for losing relief pitcher Luis Vizcaino via free agency.
There is no better reminder of that pick's value than to review the success of Chamberlain, the Compensation Round A-pick from the 2006 Draft and the 41st selection overall.
"It's a good crop of players out there," Oppenheimer said. "I think the Draft has some depth to it. I'm not sure how many potential superstars there are in this Draft, but from what we've seen, it has some depth and there should be some good players. There's a huge difference between players one through five and players 25 through 30, but we'll still be happy with what we get."
MLB.com will carry every pick of the 2008 First-Year Player Draft, which takes place June 5-6 at The Milk House at Disney's Wide World of Sports Complex in Orlando, Fla. Day 1 coverage begins at 2 p.m. ET with a simulcast of ESPN2's broadcast of the first round and compensation picks. The remaining rounds on Day 1 will be shown exclusively at
MLB.com, with live analysis on site from MLB.com Draft guru Jonathan Mayo.
Several of the top amateur prospects are expected in attendance in Orlando for Day 1 of the Draft, and each of the 30 Major League clubs will be represented by front-office executives and baseball luminaries. Fans are welcome to attend Day 1 of the Draft, and admission to The Milk House is free with seating limited to a first-come, first-served basis.
Day 2 will get under way at 11:30 a.m. and continue through Round 50, if necessary. Every pick on Day 2 can be heard live at MLB.com.
Here's a glance at what the Yankees have in store as the First-Year Player Draft approaches:
In about 50 words
The Yankees have shown that they are not shy about taking financial risks other teams might not -- see last year's top pick, Andrew Brackman, who won't pitch until 2009, but still has executives excited. It's not just pitching. Catcher Austin Romine and infielders Bradley Suttle and Carmen Angelini have also proven buzzworthy.
The organization's philosophy is to look for the most talented and Major League-ready player available on the board at the time of the selection, regardless of position, and allow the rest to shake out where it may.
"You always hope to put pitching into the system, and it'd be nice to put some big arms into the system," Oppenheimer said. "It would be nice to put some athletic guys who could potentially hit in the middle of the lineup. Those guys, there's not that many of them to pick from. In terms of a particular position, I'm not going to try to shove a square peg into a round hole or anything like that. We're going to pick what's the best out there."
There's been a lot of talk about the Yankees repeating -- in a way -- what they did in last year's Draft by taking an injured college pitcher with their first-round pick. Oppenheimer said that just watching Brackman work off a mound in Tampa has the organization feeling very good about its decision to snag a bright young prospect with a little cleaning up to do. Then again, the Yankees would need a striking case to repeat the course of action.
"It has to be a pretty darn special guy, and Brackman has a lot of things going for him," Oppenheimer said. "On top of his stuff, he has athleticism and he was a basketball player. He was really what we thought was very, very special."
If the Yankees decided to draft according to Major League need, their two top priorities might be to select a power-hitting first baseman and a good left-handed arm. Of course, the progress pipeline doesn't normally feed the Bronx that quickly. Last year, the club brought Angelini up to Yankee Stadium for a taste of what life might be like if he makes it up to The Show. A shortstop, Angelini even took a locker for a day -- across the room from Derek Jeter, who didn't seem irked by the visit.
Though it selected 40 collegiate players out of 50 spots last year, four of New York's top 10 were high school players. Last year, the Yankees took 24 position players and 26 pitchers.
"We're just going to try to line them up the best we can," Oppenheimer said. "We'd like to take the guy with the highest ceiling, who is closest to the big leagues. Sometimes that's college and sometimes it's high school. We try to weigh those things and put it together, and take which one of those guys best fits that round."
Recent top picks
The Yankees selected Brackman from North Carolina State with the 30th pick in last year's Draft, despite knowing that he would likely miss all of 2008 after undergoing Tommy John elbow reconstruction surgery. Brackman is working out at the Yankees' facilities in Tampa, and is expected to begin pitching competitively in 2009.
New York's top pick in the 2006 Draft was Kennedy from the University of Southern California, who rose quickly to the Major Leagues to make his debut on Sept. 1, 2007.
High school infielder C.J. Henry was taken in the first round of the 2005 Draft and became a trade chip, helping the Yankees land Bobby Abreu from the Philadelphia Phillies in July 2006. He found his way back to the Yankees' farm system in 2007 and is currently on the Minor League disabled list.
Right-hander Dan McCutchen, a 13th-round selection in 2006 from the University of Oklahoma, was recently promoted to Triple-A Scranton/Wilkes-Barre and could be among the next group of Yankees to experience big league life. McCutchen had a 2.55 ERA in nine starts at Double-A Trenton before being promoted.
Right-hander David Robertson, a 17th-round pick in 2006, has moved quickly up the ladder and should merit consideration for a promotion to Yankee Stadium at some point this season. Robertson was promoted from Double-A Trenton in May, where he had a 0.96 ERA in nine games, walking six and striking out 26 in 18 2/3 innings.
In The Show
Chamberlain, the 41st pick in the 2006 Draft, has made a huge splash as a big league reliever and, soon, perhaps as a starter. The Yankees' first-round pick that year, Kennedy, started this season in the rotation, but has struggled and is currently on the disabled list.