That has lead me to rank the top picks Boston has had from 1990 (the year before I started collecting) through 2012 by their contributions to the Red Sox, either through their own stats or the player they were traded for. I did not rank the players since 2013 because none of them have made it to the Majors yet or been traded away. Their records are too incomplete. This is a completely subjective ranking based entirely on my own opinions.
1. DUSTIN PEDROIA (2nd Round, 2004)
2. NOMAR GARCIAPARRA (1st Round, 1994)
3. JON LESTER (2nd Round, 2002)
4. JACOBY ELLSBURY (1st Round, 2005)
Ellsbury was a monster in 2011 and probably should have won the MVP with his 30/30 season (the first ever by a Red Sox player). But that was his only real great season, and most other years he was merely decent. He did help Boston to two World Championships though and set a Red Sox record for stolen bases in a season with 70. Ellsbury lead the league in stolen bases three times.
5. TROT NIXON (1st Round, 1993)
6. AARON SELE (1st Round, 1991)
7. MATT BARNES (1st Round, 2011)
8. KELLY SHOPPACH (2nd Round, 2001)
9. DAVID MURPHY (1st Round, 2003)
10. DEVEN MARRERO (1st Round, 2012)
11. FRANKIE RODRIGUEZ (2nd Round, 1990)
12. CASEY KELLY (1st Round, 2008)
And now we are getting into players who never actually played for Boston. Kelly was a very good prospect and looked ready to make the leap to the Major Leagues after the 2010 season, but then he was traded to San Diego in the Adrian Gonzalez trade. The injuries slowed things down a little bit. He has made it to the Majors finally but has failed to impress so far. But he did get Boston one terrific season of Adrian Gonzalez and one half of another good season as well. That trade also cost Boston Anthony Rizzo though.
14. NICK HAGADONE (1st Round, 2007)
Hagadone was technically a supplemental first rounder. Boston lost their top pick to the Dodgers for signing away J.D. Drew. Not much was ever really expected of Hagadone but he has turned into a fairly reliable middle reliever. Of course that has occurred after being traded away in midseason 2009 to Cleveland in exchange for Victor Martinez. That trade also worked out pretty well for Boston.
15. ADAM EVERETT (1st Round, 1998)
16. PHIL DUMATRAIT (1st Round, 2000)
17. RICK ASADOORIAN (1st Round, 1999)
18. JOSH GARRETT (1st Round, 1996)
19. JASON PLACE (1st Round, 2006)
20. KOLBRIN VITEK (1st Round, 2010)
21. JOHN CURTICE (1st Round, 1997)
23. ANDY YOUNT (1st Round, 1995)
Yount might have made it, but we will never know. After visiting the grave of a friend who died senselessly in an accident, he squeezed a bottle in anger so tightly that it shattered lacerating several tendons in his pitching hand. Several surgeries later and Yount was eventually released. He attempted a comeback a few years later in the Tigers system, but never made it above High-A. He pitched in just 13 games in the Red Sox system. Boston's most successful signee in 1995 was Paxton Crawford, so yet another bad draft. Juan Pena looked to be a star but injuries ended his career. Boston drafted Pat Burrell but he did not sign. Roy Halladay was picked just two places after Yount.
Since 2012, Boston's top picks were Trey Ball, Michael Chavis, and Andrew Benintendi, respectively. Ball and Chavis have struggled, though it is still too early to give up on them entirely. Benintendi, on the other hand, looks like he could make it to the Majors sooner, rather than later. It is obvious that a variety of things can happen to make drafting top talent an iffy proposition. That is why I think teams frequently over-value their draft picks and why I don't spend a ton of time and money collecting players before they make it to the Major Leagues.