Over the years the Jays have had many first round picks that worked out (Halladay) and many that didn't (Beede). But what if the Jays took the guy who came after their #1 pick - IE: instead of Romero they drafted Troy Tulowitzki. How often did the Jays make the right choice, and how often the wrong one?
Stats via Baseball-Reference.com
Wins are defined as most WAR, in case of guys making majors vs other one not that counts as a win if the guy got 100 or more games in. Sub 100 games it really didn't matter except with starting pitchers (30 starts should work). Bold indicates 'winner', no bolding indicates 'no decision' due to neither doing anything in the majors of note. A guy with negative WAR can be worthwhile if he had a good year or two.
Year: drafted (results) next pick (results)
Early Years (Pat Gillick mainly)
11 picks, 2 wins (Moseby, Cerutti) 7 losses (many ugly) 2 no decisions - very ugly period for the draft with just 30 WAR while the missed pick in '81 had more than that on his own while the missed '77 pick was almost there on his own.
1977: Tom Goffena (SS-never reached majors) Dave Henderson (OF 1538 games, 27.3 WAR, 108 OPS+, All-Star, 946 OPS in playoffs over 141 PA)
1978: Lloyd Moseby (CF-led in most Jay areas when retired 24.1 WAR) Hubie Brooks (1600 games, 10.6 WARRF/3B/SS) both All Stars
1979: Jay Schroeder (CA-never reached majors) Brad Komminsk (OF - 376 games, 637 OPS)
1980: Garry Harris (SS-never reached majors) Ken Daley (RP-3.0 WAR over 385 games)
1981: Matt Williams (P-10 games) Kevin McReynolds (OF-31 WAR over 1500 games)
1981b: John Cerutti (P 6.0 WAR over 229 games) Dave Anderson (SS 3.2 WAR over 873 games) [compensation for Roy Howell]
1982: Augie Schmidt (SS-never reached majors) Jimmy Jones (RHP 153 games negative 3.1 WAR) - Dwight Gooden went shortly afterwards
1983: Matt Stark (C-13 games) Ray Hayward (LHP 19 games) [Roger Clemens drafted #19, Stark #9]
1984: no pick (lost due to signing Dennis Lamp)
1985: Greg David (OF-never reached majors) Randy Nosek (RHP 5 games)
1986: Earl Sanders (RHP-never reached majors) Mike Fetters (RHP 7.3 WAR over 620 games)
1987: Alex Sanchez (RHP 4 games) Jack Armstrong (RHP All-Star 0.7 WAR) Craig Biggio went shortly after
After all that futility (Cerutti & Moseby only ones worthwhile) something changed.
14 picks, 5 wins 5 losses 4 no decisions - better, but needs improvement, 90-100 WAR net. Johnny Damon the only big loss.
1988: Ed Sprague (3B 2.8 WAR, All-Star 1200 games) Rico Brogna (1B -1.9 WAR 848 games)
1989: Eddie Zosky (SS 44 games) Scott Bryant (OF-never reached majors)
1990: Steve Karsay (RHP 9.9 WAR over 358 games) Lance Dickson (LHP 3 games)
1991: regular pick lost for signing Ken Dayley (see 1980)
1991a: Shawn Green (RF 29.4 WAR over 1951 games) Eduardo Perez (1B 754 games 0.2 WAR) - via losing Buddy Black
1991b: Jeff Ware (RHP 18 games) Bobby Jones (RHP 6.4 WAR over 245 games) - via losing George Bell
1991c: Dante Powell (SS 70 games) Scott Hatteberg (CA/1B 8.3 WAR over 1314 games and a book) via losing Buddy Black
1992: Todd Steverson (OF 31 games) Dan Serafini (LHP -1.0 WAR over 105 games)
1992a: Shannon Stewart (OF 19.8 WAR over 1386 games) Benji Grigsby (RHP never reached majors) via losing Tom Candiotti
1992b: Brandon Cromer (SS-never reached majors) Johnny Damon (OF 50.9 WAR so far over 2389 games) via losing Tom Candiotti
1993: lost regular pick to sign Paul Molitor
1993a: Chris Carpenter (RHP 29.6 WAR over 339 games) Alan Benes (RHP 0.6 WAR over 115 games) via losing Tom Henke
1993b: Matt Farner (OF never reached majors) Kelcey Mucker (OF never reached majors) via losing David Cone
1993c: Jeremy Lee (RHP never reached majors) Jays had next pick via losing Tom Henke
1993d: Mark Lukasiewicz (LHP 41 games) Charles Rice (1B never reached majors) via losing Jimmy Key
1994: Kevin Witt (draft at SS 1B/OF in majors 146 games -0.9 WAR) Jay Payton (OF 14.7 WAR over 1259 games)
Gord Ash takes over
10 picks, 7 wins (counting McGowan) 1 loss 2 no decisions - WOW Over 100 WAR so far while none of the 'next choices' have reached 5 WAR (6 of 10 Jay picks have).
1995: Roy Halladay (RHP 59 WAR so far over 370 games) Ryan Jaroncyk (SS never reached majors)
1996: Billy Koch (RHP 6.0 WAR over 379 games in relief) John Patterson (RHP 4.4 WAR 88 games)
1996a: Joe Lawrence (SS -1 WAR over 55 games) Todd Noel (RHP never reached majors) via losing Alomar
1996b: Pete Tucci (1B never reached majors) Corey Lee (LHP 1 game in majors) via losing Alomar
1997: Vernon Wells (CF 25.3 WAR over 1489 games) Geoff Goetz (LHP never reached majors)
1998: Felipe Lopez (SS 7 WAR over 1184 games) Sean Burroughs (3B 1.1 WAR over 493 games)
1999: Alexis Rios (10.8 WAR over 1110 games) Vince Faison (OF never reached majors)
2000: Miguel Negron (OF never reached majors) Sean Burnett (LHP 2.7 WAR over 269 games)
2000a: Dustin McGowan (RHP 1.7 WAR over 76 games) Dustin Moseley (1.6 WAR over 100 games) via losing Graeme Lloyd
2001: Gabe Gross (OF 5 WAR over 657 games) Kris Honel (RHP never reached majors)
JP Ricciardi era begins
14 picks, 4 wins (Hill, Snider, JPA, Cecil) 3 losses (Adams, Romero, Cooper) 7 no decisions
Seems unfair for Romero to be a loss, but Tulowitzki was debated on by the Jays.
2002: Russ Adams (SS -1.1 WAR over 286 games) Scott Kazmir (LHP 16.7 WAR over 180 games)
2003: Aaron Hill (2B 16.1 WAR over 873 games) Ryan Wagner (RHP -0.6 WAR over 148 games)
2004: David Purcey (LHP -0.7 WAR over 87 games) Scott Elbert (LHP -0.1 WAR over 58 games)
2004a: Zach Jackson (LHP -0.7 WAR over 22 games) Justin Orenduff (RHP never reached majors) via losing Kelvim Escobar
2005: Ricky Romero (LHP 10.5 WAR over 86 games) Troy Tulowitzki (SS 23.7 WAR over 674 games)
2006: Travis Snider (OF 0.1 WAR over 232 games) Chris Marrero (OF still in minors)
2007: J.P. Arencibia (CA 0.4 WAR over 106 games) Tim Alderson (RHP still in minors)
2007a: Kevin Ahrens (3B still in minors) Blake Beavan (RHP 8 games) via losing Frank Catalanotto
2007b: Brett Cecil (LHP 3.1 WAR over 46 games) James Adkins (LHP still in minors) via losing Justin Speier
2007c: Justin Jackson (SS still in minors) Drew Cumberland (SS still in minors) via losing Frank Catalanotto
2007d: Trystan Magnuson (RHP 9 games) Mitch Canham (CA still in minors) via losing Ted Lilly
2008: David Cooper (1B 13 games) Ike Davis (1B 3.8 WAR over 138 games)
2009: Chad Jenkins (RHP still in minors) Jiovanni Mier (SS still in minors)
2009a: James Paxton (LHP not signed, in minors) Josh Phegley (CA still in minors) via losing A.J. Burnett
Alex Anthopoulos Era begins - 9 picks, none in majors for either our picks or next
9 picks already, no one in majors yet so no decisions across the board
2010: Deck McGuire (RHP in minors) Yasmani Grandal (CA in minors)
2010a: Aaron Sanchez (RHP in minors) Matt Lipka (SS in minors) via losing Marco Scutaro
2010b: Noah Syndergaard (RHP in minors) Anthony Ranaudo (RHP in minors) via not signing James Paxton
2010c: Asher Wojciechowski (RHP in minors) Drew Vettleson (OF in minors) via losing Rod Barajas
2011: Tyler Beede (RHP did not sign) Kolten Wong (2B 886 OPS in A ball)
2011a: Jacob Anderson (OF) Henry Owens (OF) via losing Scott Downs
2011b: Joseph Musgrove (RHP) Keenyn Walker (OF) via losing John Buck
2011c: Dwight Smith (OF) Brett Austin (CA) via losing Kevin Gregg
2011d: Kevin Comer (RHP) Jace Peterson (SS) via losing Miguel Olivo
So for convoluted you get Jays 3rd round pick in 2006 (used by Florida to get Torre Langley, a catcher who has 2 games in AA so far) exchanged for AJ Burnett who was lost but gained James Paxton who didn't sign so the Jays got Noah Syndergaard.
So, what does this mean?
Gillick was horrid initially, then decent before he left. Imagine how good the 80's/90's Jays would've been if Gillick took the guy after the one he did take. Not to mentions other guys he skipped who were drafted shortly after the Jays poor choice (Clemens, Gooden, etc.)
Ash, while horrid in the trade and free agent markets was amazing for the first round of the draft. That has to be one of the best records ever. No question he is the first round king of Jays GM's (so far).
JP Ricciardi was solid, his biggest mistakes on paper (Kazmir and Tulowitzki) are mitigated by Kazmir's collapse and Romero's potential ace status (could catch Tulowitzki if the stars align but I wouldn't bet on it). This story still has chapters to be written. I know Cecil doesn't have 100 games, but he is such a clear win so far I felt I should count him.
Anthopoulos is still to be decided, but it is amazing that he has had 9 first round picks in just 2 years. No other Jay GM has more than 3 in their first 2 years (Ash with Halladay, Koch and Lawrence - 2 out of 3 ain't bad). Still, it will be hard to match Moseby (Gillick's 2nd year) or Halladay (Ash's first). At one time it looked like Hill (JP's 2nd) would be hard to match as well, but not any more. With luck those 9 picks (8 signed) will have net value above any other Jays GM's first 2 years.