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| First Round Draft Pick History |
| 1 | 8 | 8 | 2000 | Annual Draft | P | Brad | Penny | MLB |
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| 1 | 5 | 5 | 1999 | Annual Draft | P | A.J. | Burnett | MLB |
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| 1 | 10 | 10 | 1998 | Annual Draft | 3B | Aramis | Ramirez | MLB |
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| 1 | 5 | 5 | 1997 | Annual Draft | SS | Miguel | Tejada | MLB |
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| 1 | 10 | 10 | 1996 | Annual Draft | 2B | Luis | Castillo | MLB |
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| 1 | 7 | 7 | 1995 | Inaugural Draft | 1B | Frank | Thomas | MLB |
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| Complete Draft History |
| 1 | 8 | 8 | 2000 | Annual Draft | P | Brad | Penny | MLB |
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| 2 | 7 | 31 | 2000 | Annual Draft | C | Toby | Hall | MLB |
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| 3 | 7 | 55 | 2000 | Annual Draft | OF | Luis | Matos | MLB |
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| 4 | 7 | 79 | 2000 | Annual Draft | 3B | Chris | Truby | MLB |
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| 5 | 7 | 103 | 2000 | Annual Draft | 2B+ | Bobby | Smith | MLB |
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| 6 | 7 | 127 | 2000 | Annual Draft | 1B | Eric | Munson | MLB |
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| 7 | 7 | 151 | 2000 | Annual Draft | P | Ed | Vosberg | MLB |
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| 8 | 7 | 175 | 2000 | Annual Draft | OF+ | Lou | Collier | MLB |
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| 9 | 7 | 199 | 2000 | Annual Draft | P | Matt | Kinney | MLB |
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| 10 | 7 | 223 | 2000 | Annual Draft | P | Alan | Benes | MLB |
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| 11 | 7 | 247 | 2000 | Annual Draft | P | Kevin | Beirne | MLB |
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| 12 | 7 | 271 | 2000 | Annual Draft | P | Mark | Clark | MLB |
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| 1 | 5 | 5 | 1999 | Annual Draft | P | A.J. | Burnett | MLB |
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| 2 | 7 | 31 | 1999 | Annual Draft | P | Doug | Davis | MLB |
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| 3 | 7 | 55 | 1999 | Annual Draft | OF | Chris | Singleton | MLB |
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| 4 | 7 | 79 | 1999 | Annual Draft | P | Lou | Pote | MLB |
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| 5 | 7 | 103 | 1999 | Annual Draft | 2B+ | John | McDonald | MLB |
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| 6 | 7 | 127 | 1999 | Annual Draft | P | Jimmy | Anderson | MLB |
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| 7 | 7 | 151 | 1999 | Annual Draft | P | Tom | Davey | MLB |
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| 8 | 7 | 175 | 1999 | Annual Draft | P | Will | Cunnane | MLB |
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| 9 | 7 | 199 | 1999 | Annual Draft | P | Dan | Reichert | MLB |
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| 10 | 7 | 223 | 1999 | Annual Draft | C | Chris | Turner | MLB |
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| 11 | 7 | 247 | 1999 | Annual Draft | P | Miguel | Del Toro | MLB |
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| 1 | 10 | 10 | 1998 | Annual Draft | 3B | Aramis | Ramirez | MLB |
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| 2 | 11 | 35 | 1998 | Annual Draft | P | John | Rocker | MLB |
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| 3 | 10 | 58 | 1998 | Annual Draft | P | Brian | Meadows | MLB |
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| 4 | 11 | 83 | 1998 | Annual Draft | P | Jesus | Sanchez | MLB |
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| 5 | 10 | 106 | 1998 | Annual Draft | C+ | Bobby | Hughes | MLB |
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| 6 | 11 | 131 | 1998 | Annual Draft | P | Bill | Risley | MLB |
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| 7 | 10 | 154 | 1998 | Annual Draft | OF | Manny | Martinez | MLB |
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| 8 | 11 | 179 | 1998 | Annual Draft | P | Terry | Mathews | MLB |
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| 9 | 10 | 202 | 1998 | Annual Draft | P | Rick | DeHart | MLB |
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| 10 | 11 | 227 | 1998 | Annual Draft | P | Carlton | Loewer | MLB |
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| 11 | 10 | 250 | 1998 | Annual Draft | P | Jeff | Kubenka | MLB |
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| 12 | 11 | 275 | 1998 | Annual Draft | P | Keith | Glauber | MLB |
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| 13 | 10 | 298 | 1998 | Annual Draft | P | Travis | Baptist | MLB |
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| 14 | 11 | 323 | 1998 | Annual Draft | P | Jeff | McCurry | MLB |
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| 15 | 10 | 346 | 1998 | Annual Draft | P | Frank | Lankford | MLB |
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| 16 | 11 | 371 | 1998 | Annual Draft | P | Eric | Weaver | MLB |
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| 1 | 5 | 5 | 1997 | Annual Draft | SS | Miguel | Tejada | MLB |
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| 2 | 3 | 27 | 1997 | Annual Draft | P | Brett | Tomko | MLB |
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| 3 | 3 | 51 | 1997 | Annual Draft | 3B+ | Kevin | Orie | MLB |
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| 4 | 3 | 75 | 1997 | Annual Draft | P | Pete | Smith | MLB |
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| 5 | 3 | 99 | 1997 | Annual Draft | P | Jim | Pittsley | MLB |
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| 6 | 3 | 123 | 1997 | Annual Draft | OF+ | Ryan | McGuire | MLB |
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| 7 | 3 | 147 | 1997 | Annual Draft | P | Ramon | Tatis | MLB |
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| 8 | 3 | 171 | 1997 | Annual Draft | P | Reggie | Harris | MLB |
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| 9 | 3 | 195 | 1997 | Annual Draft | P | Jeff | McCurry | MLB |
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| 10 | 3 | 219 | 1997 | Annual Draft | P | Heath | Murray | MLB |
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| 11 | 3 | 243 | 1997 | Annual Draft | P | Rick | Trlicek | MLB |
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| 12 | 3 | 267 | 1997 | Annual Draft | P | Takashi | Kashiwada | MLB |
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| 13 | 3 | 291 | 1997 | Annual Draft | P | John | Burke | MLB |
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| 1 | 10 | 10 | 1996 | Annual Draft | 2B | Luis | Castillo | MLB |
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| 2 | 10 | 34 | 1996 | Annual Draft | P | Osvaldo | Fernandez | MLB |
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| 3 | 10 | 58 | 1996 | Annual Draft | P | Paul | Wilson | MLB |
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| 4 | 10 | 82 | 1996 | Annual Draft | P | Archie | Corbin | MLB |
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| 5 | 10 | 106 | 1996 | Annual Draft | 3B+ | Kim | Batiste | MLB |
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| 6 | 10 | 130 | 1996 | Annual Draft | OF+ | Chris | Gwynn | MLB |
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| 7 | 10 | 154 | 1996 | Annual Draft | P | Ron | Blazier | MLB |
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| 8 | 10 | 178 | 1996 | Annual Draft | P | Marcus | Moore | MLB |
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| 9 | 10 | 202 | 1996 | Annual Draft | C | Izzy | Molina | MLB |
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| 10 | 10 | 226 | 1996 | Annual Draft | P | Dave | Wainhouse | MLB |
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| 11 | 10 | 250 | 1996 | Annual Draft | OF | Glenn | Murray | MLB |
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| 12 | 10 | 274 | 1996 | Annual Draft | P | Paul | Fletcher | MLB |
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| 1 | 7 | 7 | 1995 | Inaugural Draft | 1B | Frank | Thomas | MLB |
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| 2 | 18 | 42 | 1995 | Inaugural Draft | OF | Tony | Gwynn | MLB |
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| 3 | 7 | 55 | 1995 | Inaugural Draft | OF | Dante | Bichette | MLB |
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| 4 | 18 | 90 | 1995 | Inaugural Draft | P | Troy | Percival | MLB |
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| 5 | 7 | 103 | 1995 | Inaugural Draft | C | Charles | Johnson | MLB |
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| 6 | 18 | 138 | 1995 | Inaugural Draft | OF | Derek | Bell | MLB |
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| 7 | 7 | 151 | 1995 | Inaugural Draft | 2B | Carlos | Baerga | MLB |
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| 8 | 18 | 186 | 1995 | Inaugural Draft | 3B+ | Kevin | Seitzer | MLB |
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| 9 | 7 | 199 | 1995 | Inaugural Draft | C | Mike | Matheny | MLB |
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| 10 | 18 | 234 | 1995 | Inaugural Draft | SS | Gary | DiSarcina | MLB |
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| 11 | 7 | 247 | 1995 | Inaugural Draft | 1B | Eddie | Murray | MLB |
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| 12 | 18 | 282 | 1995 | Inaugural Draft | P | Sterling | Hitchcock | MLB |
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| 13 | 7 | 295 | 1995 | Inaugural Draft | P | Kent | Mercker | MLB |
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| 14 | 18 | 330 | 1995 | Inaugural Draft | P | Doug | Drabek | MLB |
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| 15 | 7 | 343 | 1995 | Inaugural Draft | P | Tom | Henke | MLB |
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| 16 | 18 | 378 | 1995 | Inaugural Draft | P | Terry | Mulholland | MLB |
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| 17 | 7 | 391 | 1995 | Inaugural Draft | P | Ricky | Bones | MLB |
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| 18 | 18 | 426 | 1995 | Inaugural Draft | P | Lee | Smith | MLB |
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| 19 | 7 | 439 | 1995 | Inaugural Draft | C | Don | Slaught | MLB |
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| 20 | 18 | 474 | 1995 | Inaugural Draft | P | Kevin | Gross | MLB |
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| 21 | 7 | 487 | 1995 | Inaugural Draft | P | Bryce | Florie | MLB |
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| 22 | 18 | 522 | 1995 | Inaugural Draft | 2B | Lou | Whitaker | MLB |
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| 23 | 7 | 535 | 1995 | Inaugural Draft | 3B+ | Russ | Davis | MLB |
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| 24 | 18 | 570 | 1995 | Inaugural Draft | SS+ | Alan | Trammell | MLB |
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| 25 | 7 | 583 | 1995 | Inaugural Draft | P | Larry | Casian | MLB |
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| 26 | 18 | 618 | 1995 | Inaugural Draft | P | Ron | Villone | MLB |
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| 27 | 7 | 631 | 1995 | Inaugural Draft | OF | Curtis | Goodwin | MLB |
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| 28 | 18 | 666 | 1995 | Inaugural Draft | P | Jeff | Tabaka | MLB |
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| 29 | 7 | 679 | 1995 | Inaugural Draft | P | Mark | Kiefer | MLB |
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| 30 | 18 | 714 | 1995 | Inaugural Draft | P | Paul | Wagner | MLB |
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| 31 | 7 | 727 | 1995 | Inaugural Draft | P | Mike | Birkbeck | MLB |
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| 32 | 18 | 762 | 1995 | Inaugural Draft | OF | Alex | Diaz | MLB |
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| 33 | 7 | 775 | 1995 | Inaugural Draft | P | Mike | Butcher | MLB |
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| 34 | 18 | 810 | 1995 | Inaugural Draft | OF | Kevin | Bass | MLB |
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| 35 | 7 | 823 | 1995 | Inaugural Draft | C | Randy | Knorr | MLB |
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| 36 | 18 | 858 | 1995 | Inaugural Draft | 3B+ | Spike | Owen | MLB |
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| 37 | 7 | 871 | 1995 | Inaugural Draft | C | John | Marzano | MLB |
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| 38 | 18 | 906 | 1995 | Inaugural Draft | P | Rob | Dibble | MLB |
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| 39 | 7 | 919 | 1995 | Inaugural Draft | P | Aaron | Small | MLB |
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| 40 | 18 | 954 | 1995 | Inaugural Draft | P | Steve | Bedrosian | MLB |
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