SUCCESS (Amateur Drafts 1987-1991)

Interestingly, the Yankees had the best record in baseball for the decade of the 1980s, but only made the playoffs twice, losing in the ALCS to the Royals in 1980 and to the Dodgers in the 1981 World Series. The 1987-1991 period was not a good one for Yankee fans; the team's initial response to the rise of the Mets was a tailspin that bottomed out at 67-95 in 1990, and the team wasn't competitive until 1993, under Gene Michael and Buck Showalter. The interference of owner George Steinbrenner was partly to blame for the Yankees' directionless stumbling in the late 1980s, as he hired Billy Martin to manage three separate times, changed GM's almost as frequently, and allowed Dallas Green the rare opportunity to wreck both franchises. He hired Gene Michael, who had managed the Yankees in parts of 1981 and 1982, as GM, and allowed Michael more autonomy than previous GM's. The eventual results were 4 championships. Here are the humble beginnings.

1987
7) RHP Dave Eiland. 12-27, 5.74 career. 6-10, 5.23 as a Yankee. Pitched for Yankees, Padres, and Rays, 1988-2000. Eiland is now the Yankee pitching coach. His playing career was unsuccessful, in part due to the Yankees rushing him to the majors.
Later rounds: CF/LF Gerald Williams, C Brad Ausmus.
Nothing to see here. Move along.

1988
6) LHP Jeff Johnson. 8-16, 6.52 for Yankees, 1991-1993.
9) 2B Pat Kelly .249/.307/.369 career, .251/.300/.365 as a Yankee. Bench player for Yankees, Cardinals, Blue Jays, 1991-1999. Kelly played for the 1996 champs, but didn't make the postseason roster.
10) RHP Kenny Greer. 1-2, 4.85 in 13 innings with '93 Mets and '95 Giants.
Later rounds: 3B Russ Davis, CF/LF Deion Sanders, LF/RF Orlando Palmeiro (did not sign), 2B Fernando Vina (did not sign).

1989
2) SS/2B/3B Andy Fox .239/.324/.338 career, .200/.287/.264 as a Yankee. Bench player for Yankees, Diamondbacks, Marlins, Expos, Rangers, 1996-2004.
5) 1B J.T. Snow .268/.357/.427 career, went 2-for-14 for 1992 Yankees. Played for Yankees, Angels, Giants, Red Sox, 1992-2006. Snow had two 100 RBI seasons, in 1995 and 1997, and had 1509 career hits and 189 homers, in addition to being a great defensive 1B. He batted .327 in the postseason. He was traded for 2 seasons of Jim Abbott, who went 20-22 in a Yankee uniform. Oops.
7) RHP Russ Springer. 36-45, 4.52 career. 0-0, 6.19 ERA in 16 innings for 1992 Yankees. Pitched for Yankees, Angels, Phillies, Astros, Diamondbacks, Braves, Cardinals, A's, Rays. Still active. Had his best seasons for Tony LaRussa at 38 and 39. Fastball/slider middle reliever who took a long time to find his command. Throw-in in the Jim Abbott trade.
9) LHP Sterling Hitchcock, 74-76, 4.80 career. 22-24, 5.15 as a Yankee. Hitchcock proved to be a very valuable commodity. Packaged with Russ Davis, he brought the Yankees Tino Martinez and Jeff Nelson. He pitched well for the Padres in 1998 and 1999, but not nearly well enough to make it worth keeping him. Hitchcock threw hard but straight, and always allowed too many home runs. His career postseason record is 4-0 with a 1.76 ERA. Pitched for Yankees, Mariners, Padres, Cardinals, 1992-2004.

1990
1) CF/RF Carl Everett .271/.341/.462 career. Played for Marlins, Mets, Astros, Red Sox, Rangers, White Sox, Expos, Mariners, 1993-2006. Doesn't believe in dinosaurs. Everett was lost to the Marlins in the expansion draft. While Everett had great tools and had some excellent seasons-- 59 HR's, 216 RBI, and 41 steals in 1999-2000, he was a negative clubhouse influence and he was usually more trouble than he was worth. He finished with 1304 hits and 202 HR's, but was traded in his prime for Adam Everett, which should tell you something.
2) 2B Robert Eenhoorn .239/.260/.328 career. 5-for-32 as a Yankee in parts of 1994-96. Played for Yankees and Angels, 1994-97. The Yanks didn't have much luck with infield prospects until Jeter came along.
4) LHP Kirt Ojala. 3-10, 4.71 with 1997-1999 Marlins.
6) RHP Sam Militello. 4-4, 3.89 with 1992-93 Yankees. Militello lost the strike zone in 1993, and walked 54 in 20.1 minor league innings over the next three years before shutting it down. Militello was a power pitching prospect who made 9 strong starts for the Yanks in 1992. I guess he cancels out Bill Pulsipher.
7) LF Jalal Leach. 12 at bats for 2001 Giants.
Later Rounds: OF Ricky Ledee, LHP Andy Pettitte, C Jorge Posada, LF/RF Shane Spencer. Wow.

1991
3) RF/LF Lyle Mouton .280/.339/.420 as a bench player for White Sox, Orioles, Brewers, Marlins, 1995-2001. Mouton was a righty platoon outfielder, similar to Shane Spencer but got fewer opportunities.
9) LHP Keith Garagozzo. 9.64 ERA in 9.1 innings with 1994 Twins.
This was the Brien Taylor draft. Taylor was the #1 pick of the 1991 draft, who injured his pitching shoulder in a bar fight before the 1994 season. He missed all of 1994, and walked 184 in 111.1 innings with 59 wild pitches while attempting a comeback. Whether Taylor would have made the majors and pitched successfully is unknown. His walk rate was poor even before the injury, and it's easier to project him as a Kaz Ishii/ Damian Moss fringe starter than a #1 or #2 guy.

So, the core of young players drafted by the Yankees in these years looks like:

C Jorge Posada
1B J.T. Snow
2B Fernando Vina or Pat Kelly
3B Russ Davis
LF Deion Sanders
CF Carl Everett
RF Ricky Ledee / Shane Spencer
SP Andy Pettitte
SP Sam Militello
SP Sterling Hitchcock
RP Russ Springer

While this isn't nominally more impressive than the Met drafts of the same era, it does produce a future Hall of Fame catcher, and a near-HOF starting pitcher. Plus some shrewd trading to net them Tino Martinez and Jeff Nelson. The only player on this list that the Yankees gave up on too soon was J.T. Snow.

Also-- I haven't factored in international scouting, but add to the Yankee core Bernie Williams and the Met core Edgardo Alfonzo.