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| First Round Draft Pick History |
| 1 | 6 | 6 | 2024 | Annual Draft | OF | Jasson | Dominguez | MLB |
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| 1 | 3 | 3 | 2023 | Annual Draft | SS | CJ | Abrams | MLB |
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| 1 | 10 | 10 | 2022 | Annual Draft | P | Joan | Adon | MLB |
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| 1 | 7 | 7 | 2021 | Annual Draft | P | Austin | Gomber | MLB |
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| 1 | 4 | 4 | 2020 | Annual Draft | OF | Yordan | Alvarez | MLB |
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| 1 | 14 | 14 | 2019 | Annual Draft | SP | John | Gant | MLB |
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| 1 | 12 | 12 | 2018 | Annual Draft | OF | Jose | Pirela | MLB |
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| 1 | 18 | 18 | 2017 | Annual Draft | SP | David | Phelps | MLB |
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| 1 | 2 | 2 | 2016 | Annual Draft | SP | Lance | McCullers | MLB |
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| 1 | 5 | 5 | 2015 | Annual Draft | SP | Vance | Worley | MLB |
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| 1 | 10 | 10 | 2014 | Annual Draft | P | John | Lackey | MLB |
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| 1 | 2 | 2 | 2013 | Annual Draft | SP | Scott | Diamond | MLB |
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| 1 | 5 | 5 | 2012 | Annual Draft | 1B | Anthony | Rizzo | MLB |
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| 1 | 18 | 18 | 2010 | Inaugural Draft | SP | Jake | Peavy | MLB |
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| Complete Draft History |
| 1 | 6 | 6 | 2024 | Annual Draft | OF | Jasson | Dominguez | MLB |
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| 2 | 6 | 30 | 2024 | Annual Draft | P | Randy | Vasquez | MLB |
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| 3 | 6 | 54 | 2024 | Annual Draft | P | Andrew | Vasquez | MLB |
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| 4 | 6 | 78 | 2024 | Annual Draft | P | Jackson | Wolf | MLB |
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| 5 | 6 | 102 | 2024 | Annual Draft | 2B | Jose A. | Rodriguez | MLB |
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| 6 | 6 | 126 | 2024 | Annual Draft | 1B | Jared | Young | MLB |
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| 7 | 6 | 150 | 2024 | Annual Draft | OF | Travis | Blankenhorn | MLB |
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| 1 | 3 | 3 | 2023 | Annual Draft | SS | CJ | Abrams | MLB |
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| 2 | 3 | 27 | 2023 | Annual Draft | P | Jorge | Lopez | MLB |
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| 3 | 3 | 51 | 2023 | Annual Draft | P | Steven | Wilson | MLB |
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| 4 | 3 | 75 | 2023 | Annual Draft | P | Junior | Fernandez | MLB |
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| 5 | 3 | 99 | 2023 | Annual Draft | P | Andre | Jackson | MLB |
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| 6 | 3 | 123 | 2023 | Annual Draft | P | Ray | Kerr | MLB |
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| 7 | 3 | 147 | 2023 | Annual Draft | P | Fernando | Cruz | MLB |
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| 8 | 3 | 171 | 2023 | Annual Draft | OF | Luis | Liberato | MLB |
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| 1 | 10 | 10 | 2022 | Annual Draft | P | Joan | Adon | MLB |
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| 2 | 10 | 34 | 2022 | Annual Draft | OF+ | Connor | Joe | MLB |
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| 3 | 10 | 58 | 2022 | Annual Draft | P | Luis A. | Garcia | MLB |
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| 5 | 10 | 106 | 2022 | Annual Draft | P | Brad | Wieck | MLB |
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| 6 | 10 | 130 | 2022 | Annual Draft | P | Drew | Hutchison | MLB |
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| 7 | 10 | 154 | 2022 | Annual Draft | P | Adam | Conley | MLB |
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| 1 | 7 | 7 | 2021 | Annual Draft | P | Austin | Gomber | MLB |
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| 2 | 6 | 30 | 2021 | Annual Draft | P | Luis H. | Garcia | MLB |
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| 3 | 7 | 55 | 2021 | Annual Draft | P | Travis | Lakins | MLB |
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| 4 | 6 | 78 | 2021 | Annual Draft | P | Keury | Mella | MLB |
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| 5 | 7 | 103 | 2021 | Annual Draft | P | Ben | Braymer | MLB |
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| 6 | 6 | 126 | 2021 | Annual Draft | P | Sam | Freeman | MLB |
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| 7 | 7 | 151 | 2021 | Annual Draft | P | Travis | Bergen | MLB |
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| 8 | 6 | 174 | 2021 | Annual Draft | P | Jimmy | Yacabonis | MLB |
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| 9 | 7 | 199 | 2021 | Annual Draft | P | Jose | Quijada | MLB |
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| 10 | 6 | 222 | 2021 | Annual Draft | P | Seth | Romero | MLB |
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| 1 | 4 | 4 | 2020 | Annual Draft | OF | Yordan | Alvarez | MLB |
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| 2 | 4 | 28 | 2020 | Annual Draft | P | Evan | Marshall | MLB |
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| 3 | 4 | 52 | 2020 | Annual Draft | P | Nick | Goody | MLB |
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| 3 | 24 | 72 | 2020 | Annual Draft | P | Nick | Margevicius | MLB |
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| 4 | 4 | 76 | 2020 | Annual Draft | OF | Yasmany | Tomas | MLB |
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| 5 | 4 | 100 | 2020 | Annual Draft | C | Tres | Barrera | MLB |
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| 6 | 4 | 124 | 2020 | Annual Draft | P | James | Hoyt | MLB |
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| 7 | 4 | 148 | 2020 | Annual Draft | P | Pedro | Avila | MLB |
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| 8 | 4 | 172 | 2020 | Annual Draft | P | Edinson | Volquez | MLB |
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| 9 | 4 | 196 | 2020 | Annual Draft | P | Jon | Edwards | MLB |
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| 1 | 14 | 14 | 2019 | Annual Draft | SP | John | Gant | MLB |
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| 2 | 14 | 38 | 2019 | Annual Draft | SP | Caleb | Smith | MLB |
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| 3 | 14 | 62 | 2019 | Annual Draft | SP | Matt | Koch | MLB |
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| 4 | 14 | 86 | 2019 | Annual Draft | 1B | Aramis | Garcia | MLB |
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| 5 | 14 | 110 | 2019 | Annual Draft | SP | Adrian | Sampson | MLB |
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| 6 | 14 | 134 | 2019 | Annual Draft | RP | Pat | Venditte | MLB |
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| 7 | 14 | 158 | 2019 | Annual Draft | SP | Walker | Lockett | MLB |
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| 8 | 14 | 182 | 2019 | Annual Draft | RP | Cory | Mazzoni | MLB |
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| 1 | 12 | 12 | 2018 | Annual Draft | OF | Jose | Pirela | MLB |
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| 2 | 12 | 36 | 2018 | Annual Draft | OF | Allen | Cordoba | MLB |
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| 3 | 12 | 60 | 2018 | Annual Draft | SP | Deck | McGuire | MLB |
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| 4 | 12 | 84 | 2018 | Annual Draft | SP | Bronson | Arroyo | MLB |
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| 5 | 12 | 108 | 2018 | Annual Draft | SP | Christian | Bergman | MLB |
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| 6 | 12 | 132 | 2018 | Annual Draft | SP | Edwin | Jackson | MLB |
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| 7 | 12 | 156 | 2018 | Annual Draft | SP | Dayan | Diaz | MLB |
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| 8 | 12 | 180 | 2018 | Annual Draft | RP | Jean | Machi | MLB |
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| 9 | 12 | 204 | 2018 | Annual Draft | OF | Chad | Huffman | MLB |
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| 10 | 12 | 228 | 2018 | Annual Draft | SP | Chris R. | Young | MLB |
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| 1 | 18 | 18 | 2017 | Annual Draft | SP | David | Phelps | MLB |
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| 2 | 18 | 42 | 2017 | Annual Draft | 1B | Tyler | White | MLB |
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| 3 | 18 | 66 | 2017 | Annual Draft | RP | Ryan | Buchter | MLB |
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| 4 | 18 | 90 | 2017 | Annual Draft | RP | Jumbo | Diaz | MLB |
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| 5 | 18 | 114 | 2017 | Annual Draft | SP | Eddie | Butler | MLB |
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| 6 | 18 | 138 | 2017 | Annual Draft | RP | Joba | Chamberlain | MLB |
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| 7 | 18 | 162 | 2017 | Annual Draft | OF | Jabari | Blash | MLB |
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| 8 | 18 | 186 | 2017 | Annual Draft | OF | Hernan | Iribarren | MLB |
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| 9 | 18 | 210 | 2017 | Annual Draft | C | Jesus | Sucre | MLB |
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| 10 | 18 | 234 | 2017 | Annual Draft | RP | Logan | Kensing | MLB |
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| 1 | 2 | 2 | 2016 | Annual Draft | SP | Lance | McCullers | MLB |
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| 2 | 2 | 26 | 2016 | Annual Draft | OF | Preston | Tucker | MLB |
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| 3 | 2 | 50 | 2016 | Annual Draft | SP | Colin | Rea | MLB |
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| 4 | 2 | 74 | 2016 | Annual Draft | RP | Fernando | Rodriguez | MLB |
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| 5 | 2 | 98 | 2016 | Annual Draft | OF | Alex | Dickerson | MLB |
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| 6 | 2 | 122 | 2016 | Annual Draft | SP | Taylor | Jordan | MLB |
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| 7 | 2 | 146 | 2016 | Annual Draft | RP | Bobby | LaFromboise | MLB |
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| 8 | 2 | 170 | 2016 | Annual Draft | SP | Chris | Narveson | MLB |
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| 9 | 2 | 194 | 2016 | Annual Draft | OF | Chris | Dominguez | MLB |
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| 10 | 2 | 218 | 2016 | Annual Draft | SS | Nick | Noonan | MLB |
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| 11 | 2 | 242 | 2016 | Annual Draft | RP | Carlos | Contreras | MLB |
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| 1 | 5 | 5 | 2015 | Annual Draft | SP | Vance | Worley | MLB |
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| 2 | 5 | 29 | 2015 | Annual Draft | RP | Kevin | Quackenbush | MLB |
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| 2 | 13 | 37 | 2015 | Annual Draft | SP | Dylan | Axelrod | MLB |
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| 3 | 5 | 53 | 2015 | Annual Draft | RP | Frank | Garces | MLB |
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| 4 | 5 | 77 | 2015 | Annual Draft | SP | Daniel | Corcino | MLB |
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| 5 | 5 | 101 | 2015 | Annual Draft | RP | Roy | Alvarez | MLB |
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| 6 | 5 | 125 | 2015 | Annual Draft | RP | Leonel | Campos | MLB |
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| 7 | 5 | 149 | 2015 | Annual Draft | RP | Donn | Roach | MLB |
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| 8 | 5 | 173 | 2015 | Annual Draft | SP | Charlie | Leesman | MLB |
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| 9 | 5 | 197 | 2015 | Annual Draft | SP | Jason | Lane | MLB |
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| 1 | 10 | 10 | 2014 | Annual Draft | P | John | Lackey | MLB |
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| 2 | 10 | 34 | 2014 | Annual Draft | P | Mike | Dunn | MLB |
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| 3 | 10 | 58 | 2014 | Annual Draft | OF | Reymond | Fuentes | MLB |
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| 6 | 10 | 130 | 2014 | Annual Draft | P | Rhiner | Cruz | MLB |
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| 7 | 10 | 154 | 2014 | Annual Draft | P | Thad | Weber | MLB |
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| 8 | 10 | 178 | 2014 | Annual Draft | P | Jeremy | Bonderman | MLB |
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| 1 | 2 | 2 | 2013 | Annual Draft | SP | Scott | Diamond | MLB |
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| 2 | 2 | 26 | 2013 | Annual Draft | RP | Ronald | Belisario | MLB |
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| 3 | 2 | 50 | 2013 | Annual Draft | RP | Brad | Boxberger | MLB |
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| 4 | 2 | 74 | 2013 | Annual Draft | RP | Miles | Mikolas | MLB |
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| 4 | 14 | 86 | 2013 | Annual Draft | RP | Raul | Valdes | MLB |
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| 5 | 2 | 98 | 2013 | Annual Draft | P | Tom | Layne | MLB |
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| 1 | 5 | 5 | 2012 | Annual Draft | 1B | Anthony | Rizzo | MLB |
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| 3 | 5 | 53 | 2012 | Annual Draft | P | Ryan | Mattheus | MLB |
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| 4 | 4 | 76 | 2012 | Annual Draft | P | Luis | Mendoza | MLB |
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| 5 | 5 | 101 | 2012 | Annual Draft | P | Fernando | Rodriguez | MLB |
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| 6 | 4 | 124 | 2012 | Annual Draft | OF | Cedric | Hunter | MLB |
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| 7 | 5 | 149 | 2012 | Annual Draft | P | George | Kontos | MLB |
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| 8 | 4 | 172 | 2012 | Annual Draft | P | Justin | Berg | MLB |
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| 9 | 5 | 197 | 2012 | Annual Draft | P | Andrew | Carpenter | MLB |
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| 10 | 4 | 220 | 2012 | Annual Draft | P | Juan | Perez | MLB |
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| 3 | 16 | 64 | 2011 | Annual Draft | P | Randy | Flores | MLB |
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| 4 | 11 | 95 | 2011 | Annual Draft | P | Brian | Sweeney | MLB |
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| 4 | 16 | 100 | 2011 | Annual Draft | P | Enrique | Gonzalez | MLB |
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| 5 | 16 | 112 | 2011 | Annual Draft | 1B | Mike | Baxter | MLB |
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| 6 | 16 | 156 | 2011 | Annual Draft | P | Erick | Threets | MLB |
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| 7 | 11 | 155 | 2011 | Annual Draft | P | Matt | Chico | MLB |
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| 7 | 16 | 160 | 2011 | Annual Draft | 1B | Brad | Eldred | MLB |
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| 7 | 22 | 166 | 2011 | Annual Draft | 2B | Lance | Zawadzki | MLB |
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| 8 | 16 | 212 | 2011 | Annual Draft | P | John | Parrish | MLB |
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| 9 | 16 | 240 | 2011 | Annual Draft | P | Armando | Gabino | MLB |
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| 10 | 16 | 232 | 2011 | Annual Draft | P | Romulo | Sanchez | MLB |
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| 11 | 16 | 296 | 2011 | Annual Draft | P | Robert | Ray | MLB |
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| 1 | 18 | 18 | 2010 | Inaugural Draft | SP | Jake | Peavy | MLB |
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| 2 | 18 | 42 | 2010 | Inaugural Draft | OF | Josh | Willingham | MLB |
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| 3 | 18 | 74 | 2010 | Inaugural Draft | 2B | Kazuo | Matsui | MLB |
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| 4 | 18 | 90 | 2010 | Inaugural Draft | RP | Bobby | Jenks | MLB |
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| 5 | 18 | 114 | 2010 | Inaugural Draft | 3B | Juan | Francisco | MLB |
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| 6 | 18 | 158 | 2010 | Inaugural Draft | RP | Alberto | Arias | MLB |
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| 7 | 18 | 162 | 2010 | Inaugural Draft | RP | Ken | Takahashi | MLB |
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| 8 | 18 | 186 | 2010 | Inaugural Draft | RP | Ryan | Webb | MLB |
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| 9 | 18 | 242 | 2010 | Inaugural Draft | OF | Luis | Durango | MLB |
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| 10 | 18 | 234 | 2010 | Inaugural Draft | SP | Ryan | Sadowski | MLB |
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