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| First Round Draft Pick History |
| 1 | 1 | 1 | 2021 | Annual Draft | P | Cristian | Javier |
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| 1 | 3 | 3 | 2020 | Annual Draft | P | Zac | Gallen |
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| 1 | 5 | 5 | 2020 | Annual Draft | 2B+ | Luis | Arraez |
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| 1 | 1 | 1 | 2019 | Annual Draft | SP | Brad | Keller |
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| 1 | 12 | 12 | 2019 | Annual Draft | OF | Daniel | Palka |
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| 1 | 1 | 1 | 2018 | Annual Draft | RP | Sandy | Alcantara |
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| 1 | 3 | 3 | 2018 | Annual Draft | OF | Jose | Martinez |
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| 1 | 20 | 20 | 2018 | Annual Draft | 3B | Christian | Arroyo |
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| 1 | 23 | 23 | 2018 | Annual Draft | OF | Dustin | Fowler |
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| 1 | 3 | 3 | 2017 | Annual Draft | SP | Robert | Gsellman |
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| 1 | 20 | 20 | 2016 | Annual Draft | OF | Max | Kepler |
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| 1 | 21 | 21 | 2016 | Annual Draft | SP | Williams | Perez |
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| 1 | 15 | 15 | 2015 | Annual Draft | RP | Cory | Rasmus |
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| 1 | 9 | 9 | 2014 | Annual Draft | 3B | Cody | Asche |
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| 1 | 6 | 6 | 2013 | Annual Draft | SP | Ryan | Cook |
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| 1 | 7 | 7 | 2012 | Annual Draft | 1B | Daniel | Murphy |
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| 1 | 4 | 4 | 2011 | Dispersal Draft | OF | Shin-Soo | Choo |
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| 1 | 8 | 8 | 2010 | Annual Draft | 3B | Geoff | Blum |
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| 1 | 8 | 8 | 2010 | Waiver Draft | SS | Tommy | Manzella |
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| 1 | 18 | 18 | 2009 | Inaugural Draft | SP | Cliff | Lee |
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| Complete Draft History |
| 1 | 1 | 1 | 2021 | Annual Draft | P | Cristian | Javier |
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| 2 | 17 | 41 | 2021 | Annual Draft | OF | Brent | Rooker |
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| 3 | 1 | 49 | 2021 | Annual Draft | P | Nick | Neidert |
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| 4 | 1 | 73 | 2021 | Annual Draft | P | Adonis | Medina |
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| 5 | 1 | 97 | 2021 | Annual Draft | OF | Shogo | Akiyama |
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| 6 | 1 | 121 | 2021 | Annual Draft | P | Zack | Burdi |
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| 7 | 1 | 145 | 2021 | Annual Draft | 2B+ | Andy | Young |
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| 9 | 1 | 193 | 2021 | Annual Draft | P | Joey | Gerber |
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| 10 | 1 | 217 | 2021 | Annual Draft | P | Tyler | Zuber |
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| 1 | 3 | 3 | 2020 | Annual Draft | P | Zac | Gallen |
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| 1 | 5 | 5 | 2020 | Annual Draft | 2B+ | Luis | Arraez |
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| 2 | 3 | 31 | 2020 | Annual Draft | P | Logan | Webb |
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| 3 | 3 | 59 | 2020 | Annual Draft | P | Martin | Perez |
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| 4 | 3 | 87 | 2020 | Annual Draft | OF | Dexter | Fowler |
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| 5 | 3 | 115 | 2020 | Annual Draft | C | Garrett | Stubbs |
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| 6 | 3 | 143 | 2020 | Annual Draft | OF | Dylan | Moore |
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| 7 | 3 | 147 | 2020 | Annual Draft | P | Lewis | Thorpe |
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| 8 | 3 | 199 | 2020 | Annual Draft | C | Dustin | Garneau |
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| 9 | 3 | 195 | 2020 | Annual Draft | P | Jairo | Diaz |
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| 10 | 3 | 255 | 2020 | Annual Draft | P | Austin | Pruitt |
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| 1 | 1 | 1 | 2019 | Annual Draft | SP | Brad | Keller |
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| 1 | 12 | 12 | 2019 | Annual Draft | OF | Daniel | Palka |
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| 2 | 1 | 25 | 2019 | Annual Draft | SS | Yairo | Munoz |
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| 3 | 1 | 49 | 2019 | Annual Draft | RP | Ryan | Pressly |
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| 4 | 1 | 85 | 2019 | Annual Draft | RP | Jesse | Biddle |
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| 5 | 1 | 113 | 2019 | Annual Draft | RP | Robbie | Erlin |
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| 6 | 1 | 121 | 2019 | Annual Draft | C | Jacob | Stallings |
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| 6 | 8 | 148 | 2019 | Annual Draft | RP | Justin | Miller |
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| 7 | 1 | 145 | 2019 | Annual Draft | RP | Justin | Anderson |
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| 7 | 8 | 152 | 2019 | Annual Draft | RP | Brad | Wieck |
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| 8 | 1 | 197 | 2019 | Annual Draft | SP | Ariel | Jurado |
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| 8 | 8 | 176 | 2019 | Annual Draft | C | Cam | Gallagher |
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| 9 | 1 | 225 | 2019 | Annual Draft | RP | Jeffrey | Springs |
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| 9 | 8 | 200 | 2019 | Annual Draft | 1B | Brandon | Dixon |
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| 1 | 1 | 1 | 2018 | Annual Draft | RP | Sandy | Alcantara |
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| 1 | 3 | 3 | 2018 | Annual Draft | OF | Jose | Martinez |
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| 1 | 20 | 20 | 2018 | Annual Draft | 3B | Christian | Arroyo |
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| 1 | 23 | 23 | 2018 | Annual Draft | OF | Dustin | Fowler |
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| 2 | 1 | 25 | 2018 | Annual Draft | OF | Magneuris | Sierra |
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| 3 | 1 | 49 | 2018 | Annual Draft | SP | Dillon | Peters |
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| 4 | 1 | 73 | 2018 | Annual Draft | C | Luis | Torrens |
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| 5 | 1 | 97 | 2018 | Annual Draft | RP | Andrew | Chafin |
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| 6 | 1 | 121 | 2018 | Annual Draft | RP | Jose | LeClerc |
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| 7 | 1 | 145 | 2018 | Annual Draft | RP | Adam | Morgan |
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| 8 | 1 | 169 | 2018 | Annual Draft | C | Raudy | Read |
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| 9 | 1 | 193 | 2018 | Annual Draft | 2B | Ryan | Flaherty |
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| 10 | 1 | 217 | 2018 | Annual Draft | RP | Zac | Curtis |
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| 1 | 3 | 3 | 2017 | Annual Draft | SP | Robert | Gsellman |
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| 2 | 21 | 49 | 2017 | Annual Draft | 1B | Trey | Mancini |
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| 3 | 3 | 59 | 2017 | Annual Draft | 3B | Jeimer | Candelario |
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| 4 | 18 | 102 | 2017 | Annual Draft | SP | Zach | Eflin |
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| 4 | 24 | 108 | 2017 | Annual Draft | OF | Jordan | Patterson |
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| 5 | 18 | 130 | 2017 | Annual Draft | SP | Andrew | Triggs |
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| 6 | 18 | 158 | 2017 | Annual Draft | RP | Matt | Barnes |
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| 7 | 18 | 186 | 2017 | Annual Draft | RP | A.J. | Schugel |
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| 8 | 18 | 214 | 2017 | Annual Draft | SP | Bryan | Mitchell |
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| 9 | 18 | 242 | 2017 | Annual Draft | OF | Jason | Coats |
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| 10 | 18 | 270 | 2017 | Annual Draft | RP | Mike | Morin |
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| 1 | 20 | 20 | 2016 | Annual Draft | OF | Max | Kepler |
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| 1 | 21 | 21 | 2016 | Annual Draft | SP | Williams | Perez |
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| 4 | 19 | 103 | 2016 | Annual Draft | 2B | Hector | Gomez |
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| 5 | 24 | 136 | 2016 | Annual Draft | SP | Aaron | Brooks |
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| 6 | 19 | 139 | 2016 | Annual Draft | OF | Adam | Duvall |
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| 6 | 24 | 164 | 2016 | Annual Draft | OF | Junior | Lake |
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| 7 | 19 | 187 | 2016 | Annual Draft | SP | Jon | Moscot |
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| 7 | 24 | 192 | 2016 | Annual Draft | OF | Keon | Broxton |
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| 8 | 19 | 187 | 2016 | Annual Draft | C | Luke | Maile |
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| 8 | 23 | 219 | 2016 | Annual Draft | RP | Chaz | Roe |
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| 8 | 24 | 192 | 2016 | Annual Draft | RP | Evan | Scribner |
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| 9 | 19 | 243 | 2016 | Annual Draft | RP | Luke | Jackson |
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| 9 | 24 | 216 | 2016 | Annual Draft | RP | Jason | Garcia |
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| 10 | 19 | 271 | 2016 | Annual Draft | OF | Jose | Tabata |
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| 1 | 15 | 15 | 2015 | Annual Draft | RP | Cory | Rasmus |
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| 2 | 15 | 43 | 2015 | Annual Draft | SP | Tsuyoshi | Wada |
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| 3 | 15 | 71 | 2015 | Annual Draft | RP | Blake | Treinen |
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| 4 | 15 | 87 | 2015 | Annual Draft | C | Josh | Thole |
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| 5 | 15 | 111 | 2015 | Annual Draft | SP | Scott | Carroll |
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| 6 | 15 | 155 | 2015 | Annual Draft | 1B | Travis | Ishikawa |
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| 7 | 15 | 183 | 2015 | Annual Draft | 2B | Jordany | Valdespin |
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| 8 | 15 | 211 | 2015 | Annual Draft | 3B | Jimmy | Paredes |
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| 9 | 15 | 239 | 2015 | Annual Draft | RP | Alex | Claudio |
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| 10 | 15 | 267 | 2015 | Annual Draft | RP | Drake | Britton |
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| 1 | 9 | 9 | 2014 | Annual Draft | 3B | Cody | Asche |
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| 2 | 9 | 37 | 2014 | Annual Draft | OF | Corey | Dickerson |
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| 3 | 9 | 65 | 2014 | Annual Draft | RP | Danny | Farquhar |
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| 4 | 9 | 93 | 2014 | Annual Draft | RP | Joakim | Soria |
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| 5 | 9 | 121 | 2014 | Annual Draft | SP | Jerome | Williams |
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| 6 | 9 | 149 | 2014 | Annual Draft | SP | Erik | Bedard |
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| 7 | 9 | 177 | 2014 | Annual Draft | SP | T.J. | McFarland |
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| 8 | 9 | 205 | 2014 | Annual Draft | SP | John | Gast |
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| 9 | 9 | 233 | 2014 | Annual Draft | RP | Chia-Jen | Lo |
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| 10 | 9 | 261 | 2014 | Annual Draft | RP | Eury | De La Rosa |
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| 1 | 6 | 6 | 2013 | Annual Draft | SP | Ryan | Cook |
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| 2 | 8 | 36 | 2013 | Annual Draft | RP | Jonathan | Broxton |
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| 3 | 7 | 63 | 2013 | Annual Draft | OF | A.J. | Pollock |
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| 4 | 6 | 90 | 2013 | Annual Draft | RP | J.P. | Howell |
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| 5 | 8 | 120 | 2013 | Annual Draft | 1B | Yan | Gomes |
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| 7 | 6 | 174 | 2013 | Annual Draft | SP | Justin | Grimm |
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| 8 | 8 | 204 | 2013 | Annual Draft | RP | Hector | Ambriz |
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| 9 | 7 | 231 | 2013 | Annual Draft | RP | Tommy | Hottovy |
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| 10 | 6 | 258 | 2013 | Annual Draft | OF | Kole | Calhoun |
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| 2 | 11 | 35 | 2013 | Amateur Draft | OF | Josh | Bell |
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| 1 | 7 | 7 | 2012 | Annual Draft | 1B | Daniel | Murphy |
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| 2 | 8 | 32 | 2012 | Annual Draft | RP | Javy | Guerra |
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| 3 | 7 | 55 | 2012 | Annual Draft | RP | Chance | Ruffin |
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| 4 | 8 | 80 | 2012 | Annual Draft | RP | Pedro | Strop |
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| 5 | 7 | 103 | 2012 | Annual Draft | RP | Josh | Lindblom |
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| 6 | 8 | 128 | 2012 | Annual Draft | RP | Jose | Ceda |
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| 7 | 7 | 151 | 2012 | Annual Draft | RP | Eric | Surkamp |
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| 8 | 8 | 176 | 2012 | Annual Draft | SP | Zach | McAllister |
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| 9 | 7 | 199 | 2012 | Annual Draft | 3B | Brandon | Laird |
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| 10 | 8 | 224 | 2012 | Annual Draft | RP | Danny | Farquhar |
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| 3 | 18 | 66 | 2011 | Annual Draft | SP | Jordan | Walden |
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| 4 | 7 | 79 | 2011 | Annual Draft | OF | Manny | Ramirez |
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| 4 | 9 | 81 | 2011 | Annual Draft | RP | Michael | Dunn |
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| 4 | 11 | 83 | 2011 | Annual Draft | SP | Jeremy | Jeffress |
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| 4 | 24 | 96 | 2011 | Annual Draft | RP | Henry | Rodriguez |
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| 5 | 9 | 105 | 2011 | Annual Draft | C | Tyler | Flowers |
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| 6 | 24 | 144 | 2011 | Annual Draft | RP | Mark | Melancon |
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| 1 | 4 | 4 | 2011 | Dispersal Draft | OF | Shin-Soo | Choo |
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| 2 | 4 | 11 | 2011 | Dispersal Draft | SP | Cliff | Lee |
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| 3 | 4 | 18 | 2011 | Dispersal Draft | OF | Hunter | Pence |
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| 4 | 4 | 25 | 2011 | Dispersal Draft | RP | Aroldis | Chapman |
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| 5 | 4 | 32 | 2011 | Dispersal Draft | C | John | Buck |
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| 6 | 4 | 39 | 2011 | Dispersal Draft | SP | Wade | Davis |
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| 7 | 4 | 46 | 2011 | Dispersal Draft | 1B | Paul | Konerko |
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| 8 | 4 | 53 | 2011 | Dispersal Draft | SP | Jair | Jurrjens |
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| 9 | 4 | 60 | 2011 | Dispersal Draft | SS | Orlando | Cabrera |
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| 10 | 4 | 67 | 2011 | Dispersal Draft | SP | Jake | Arrieta |
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| 11 | 4 | 74 | 2011 | Dispersal Draft | 2B | Felipe | Lopez |
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| 12 | 4 | 81 | 2011 | Dispersal Draft | SP | Chris | Volstad |
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| 13 | 4 | 88 | 2011 | Dispersal Draft | 3B | Casey | Blake |
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| 14 | 4 | 95 | 2011 | Dispersal Draft | SP | Kevin | Slowey |
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| 15 | 4 | 102 | 2011 | Dispersal Draft | C | Nick | Hundley |
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| 16 | 4 | 109 | 2011 | Dispersal Draft | RP | Joe | Thatcher |
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| 17 | 4 | 116 | 2011 | Dispersal Draft | 2B | Jayson | Nix |
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| 22 | 4 | 151 | 2011 | Dispersal Draft | SP | Vin | Mazzaro |
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| 23 | 4 | 158 | 2011 | Dispersal Draft | OF | Johnny | Damon |
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| 24 | 4 | 165 | 2011 | Dispersal Draft | RP | Takashi | Saito |
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| 25 | 4 | 172 | 2011 | Dispersal Draft | 3B | Geoff | Blum |
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| 28 | 4 | 193 | 2011 | Dispersal Draft | RP | Matt | Lindstrom |
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| 29 | 4 | 200 | 2011 | Dispersal Draft | SS | John | McDonald |
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| 30 | 4 | 207 | 2011 | Dispersal Draft | RP | Kevin | Jepsen |
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| 31 | 4 | 214 | 2011 | Dispersal Draft | RP | Trever | Miller |
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| 32 | 4 | 221 | 2011 | Dispersal Draft | RP | Jeff | Fulchino |
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| 33 | 4 | 228 | 2011 | Dispersal Draft | SP | Barry | Zito |
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| 34 | 4 | 235 | 2011 | Dispersal Draft | C | Humberto | Quintero |
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| 35 | 4 | 242 | 2011 | Dispersal Draft | OF | Reggie | Willits |
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| 37 | 4 | 256 | 2011 | Dispersal Draft | SP | Franklin | Morales |
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| 38 | 4 | 263 | 2011 | Dispersal Draft | C | John | Baker |
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| 39 | 4 | 270 | 2011 | Dispersal Draft | SP | Rick | Vandenhurk |
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| 40 | 4 | 277 | 2011 | Dispersal Draft | 3B | Esteban | German |
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| 41 | 4 | 284 | 2011 | Dispersal Draft | RP | Jeremy | Accardo |
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| 42 | 4 | 291 | 2011 | Dispersal Draft | RP | Steven | Jackson |
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| 43 | 4 | 298 | 2011 | Dispersal Draft | SP | Dan | Meyer |
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| 44 | 4 | 305 | 2011 | Dispersal Draft | OF | Lou | Montanez |
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| 1 | 8 | 8 | 2010 | Annual Draft | 3B | Geoff | Blum |
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| 2 | 8 | 32 | 2010 | Annual Draft | RP | Danys | Baez |
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| 2 | 21 | 45 | 2010 | Annual Draft | 3B | David | Freese |
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| 3 | 8 | 56 | 2010 | Annual Draft | SP | Dan | Meyer |
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| 3 | 21 | 69 | 2010 | Annual Draft | RP | Edward | Mujica |
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| 4 | 8 | 80 | 2010 | Annual Draft | RP | Tony | Sipp |
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| 5 | 8 | 104 | 2010 | Annual Draft | SP | Jason | Jennings |
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| 6 | 8 | 128 | 2010 | Annual Draft | C | J.R. | Towles |
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| 6 | 12 | 132 | 2010 | Annual Draft | OF | Sam | Fuld |
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| 1 | 8 | 8 | 2010 | Waiver Draft | SS | Tommy | Manzella |
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| 1 | 18 | 18 | 2009 | Inaugural Draft | SP | Cliff | Lee |
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| 2 | 7 | 31 | 2009 | Inaugural Draft | SP | Edinson | Volquez |
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| 3 | 18 | 66 | 2009 | Inaugural Draft | 2B | Jose | Lopez |
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| 4 | 7 | 79 | 2009 | Inaugural Draft | OF | Jacoby | Ellsbury |
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| 5 | 18 | 114 | 2009 | Inaugural Draft | 1B | Chris | Davis |
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| 6 | 7 | 127 | 2009 | Inaugural Draft | SP | Josh | Beckett |
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| 7 | 18 | 162 | 2009 | Inaugural Draft | C | Chris | Snyder |
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| 8 | 7 | 175 | 2009 | Inaugural Draft | OF | Carlos | Gomez |
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| 9 | 18 | 210 | 2009 | Inaugural Draft | OF | Shin-Soo | Choo |
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| 10 | 7 | 223 | 2009 | Inaugural Draft | 1B | Lyle | Overbay |
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| 11 | 18 | 258 | 2009 | Inaugural Draft | SS | Erick | Aybar |
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| 12 | 7 | 271 | 2009 | Inaugural Draft | 3B | Ty | Wigginton |
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| 13 | 18 | 306 | 2009 | Inaugural Draft | SP | Zach | Duke |
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| 14 | 7 | 319 | 2009 | Inaugural Draft | C | Jeff | Clement |
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| 15 | 18 | 354 | 2009 | Inaugural Draft | SS | Cesar | Izturis |
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| 16 | 7 | 367 | 2009 | Inaugural Draft | RP | Jeff | Samardzija |
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| 17 | 18 | 402 | 2009 | Inaugural Draft | 3B | Pedro | Feliz |
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| 18 | 7 | 415 | 2009 | Inaugural Draft | RP | Carlos | Villanueva |
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| 19 | 18 | 450 | 2009 | Inaugural Draft | RP | J.J. | Putz |
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| 20 | 7 | 463 | 2009 | Inaugural Draft | RP | Sergio | Romo |
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| 21 | 18 | 498 | 2009 | Inaugural Draft | RP | Jason | Motte |
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| 22 | 7 | 511 | 2009 | Inaugural Draft | RP | Dennis | Sarfate |
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| 23 | 18 | 546 | 2009 | Inaugural Draft | OF | Jose | Guillen |
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| 24 | 7 | 559 | 2009 | Inaugural Draft | SP | Garrett | Mock |
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| 25 | 18 | 594 | 2009 | Inaugural Draft | RP | Jon | Rauch |
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| 26 | 7 | 607 | 2009 | Inaugural Draft | SP | Dallas | Braden |
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| 27 | 18 | 642 | 2009 | Inaugural Draft | C | Wil | Nieves |
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| 28 | 7 | 655 | 2009 | Inaugural Draft | OF | Brandon | Jones |
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| 29 | 18 | 690 | 2009 | Inaugural Draft | SP | Shairon | Martis |
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| 30 | 7 | 703 | 2009 | Inaugural Draft | OF | Will | Venable |
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| 31 | 18 | 738 | 2009 | Inaugural Draft | SP | Jeff | Suppan |
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| 32 | 7 | 751 | 2009 | Inaugural Draft | 2B | Luis | Castillo |
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| 33 | 18 | 786 | 2009 | Inaugural Draft | RP | Bobby | Parnell |
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| 34 | 7 | 799 | 2009 | Inaugural Draft | RP | Jeremy | Accardo |
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| 35 | 18 | 834 | 2009 | Inaugural Draft | OF | Jolbert | Cabrera |
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| 36 | 7 | 847 | 2009 | Inaugural Draft | SP | Jason | Marquis |
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| 37 | 18 | 882 | 2009 | Inaugural Draft | C | Josh | Bard |
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| 38 | 7 | 895 | 2009 | Inaugural Draft | SP | Josh | Banks |
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| 39 | 18 | 930 | 2009 | Inaugural Draft | 2B | Miguel | Cairo |
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| 40 | 7 | 943 | 2009 | Inaugural Draft | RP | Joaquin | Benoit |
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