This is fun. Let's go by position.
C: I remember when the Sox called up first-round pick Rick Seilheimer for a cup of coffee. He was never heard from again. Kurt Brown was drafted even higher, but I don't remember his career.
1B: Eddie Pearson, a first round pick who didn't even hit in the minors. There was also a (Matt?) Berger who had, according to Schueler, the most power he'd ever seen. He never got out of A ball.
2B: I'm going with Willie Harris, but I'm sure I'm forgetting someone.
SS: Jason Dellaero easily over Mike Caruso.
3B: Lorenzo Gray over Chris Snopek.
LF: Jeff Abbott.
CF: Daryl Boston, but don't forget Julio Ramirez.
RF: Joe Borchard.
SP: Too easy. Almost every starting pitcher drafted in the last 25 years.
RP: Also easy. Many of the failed starters went on to fail in the bullpen.