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| First Round Draft Pick History |
| 1 | 8 | 8 | 2024 | Annual Draft | OF | Jackson | Merrill | MIN |
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| 1 | 8 | 8 | 2024 | 28 Man Draft | P | Chris | Paddack | MLB |
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| 1 | 15 | 15 | 2023 | Annual Draft | 1B | Jose | Miranda | MLB |
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| 1 | 18 | 18 | 2022 | 28 Man Draft | OF+ | Jorge | Mateo | MLB |
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| 1 | 18 | 18 | 2022 | Annual Draft | P | Tylor | Megill | MLB |
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| 1 | 7 | 7 | 2021 | 28 Man Draft | P | A.J. | Cole | MLB |
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| 1 | 7 | 7 | 2021 | Annual Draft | 3B | Alec | Bohm | MLB |
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| 1 | 4 | 4 | 2020 | 28 Man Draft | OF | Wil | Myers | MLB |
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| 1 | 5 | 5 | 2019 | Rookie Draft | SP | Brad | Keller | MLB |
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| 1 | 11 | 11 | 2018 | Rookie Draft | OF | Franchy | Cordero | MLB |
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| 1 | 12 | 12 | 2017 | Rookie Draft | 3B | Ryon | Healy | MLB |
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| 1 | 11 | 11 | 2016 | Rookie Draft | OF | Eddie | Rosario | MLB |
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| 1 | 9 | 9 | 2015 | Rookie Draft | OF | Randal | Grichuk | MLB |
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| 1 | 19 | 19 | 2015 | Rookie Draft | SP | Odrisamer | Despaigne | MLB |
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| 1 | 6 | 6 | 2014 | Rookie Draft | SP | Alex | Wood | MLB |
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| 1 | 11 | 11 | 2013 | Rookie Draft | 1B | Jose | Abreu | OS |
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| 1 | 16 | 16 | 2012 | Rookie Draft | P | Anthony | Bass | MLB |
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| 1 | 10 | 10 | 2011 | Rookie Draft | RP | Jonny | Venters | MLB |
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| 1 | 12 | 12 | 2010 | Rookie Draft | RP | Luke | Gregerson | MLB |
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| 1 | 14 | 14 | 2009 | Rookie Draft | C | John | Baker | MLB |
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| Complete Draft History |
| 1 | 8 | 8 | 2024 | Annual Draft | OF | Jackson | Merrill | MIN |
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| 1 | 8 | 8 | 2024 | 28 Man Draft | P | Chris | Paddack | MLB |
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| 2 | 8 | 32 | 2024 | 28 Man Draft | P | Seth | Martinez | MLB |
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| 2 | 8 | 32 | 2024 | Annual Draft | P | Jake | Irvin | MLB |
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| 2 | 24 | 48 | 2024 | Annual Draft | 2B+ | Jose | Caballero | MLB |
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| 3 | 8 | 56 | 2024 | Annual Draft | OF | Andy | Pages | MIN |
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| 3 | 8 | 56 | 2024 | 28 Man Draft | P | Jose | Urena | MLB |
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| 5 | 8 | 104 | 2024 | Annual Draft | C | Ben | Rortvedt | MLB |
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| 6 | 8 | 128 | 2024 | Annual Draft | P | Trent | Thornton | MLB |
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| 7 | 8 | 152 | 2024 | Annual Draft | 2B+ | Zach | Remillard | MLB |
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| 8 | 8 | 176 | 2024 | Annual Draft | 2B+ | Xavier | Edwards | MLB |
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| 9 | 8 | 200 | 2024 | Annual Draft | 3B | Andre | Lipcius | MLB |
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| 10 | 8 | 224 | 2024 | Annual Draft | 2B+ | Michael | Stefanic | MLB |
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| 1 | 15 | 15 | 2023 | Annual Draft | 1B | Jose | Miranda | MLB |
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| 2 | 15 | 39 | 2023 | Annual Draft | OF | Esteury | Ruiz | MLB |
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| 3 | 15 | 63 | 2023 | Annual Draft | P | Graham | Ashcraft | MLB |
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| 4 | 15 | 87 | 2023 | Annual Draft | P | Beau | Brieske | MLB |
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| 5 | 15 | 111 | 2023 | Annual Draft | P | Ryne | Nelson | MLB |
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| 6 | 15 | 135 | 2023 | Annual Draft | 1B | Darick | Hall | MLB |
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| 7 | 15 | 159 | 2023 | Annual Draft | OF | Jose | Azocar | MLB |
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| 8 | 15 | 183 | 2023 | Annual Draft | OF+ | Richie | Palacios | MLB |
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| 9 | 15 | 207 | 2023 | Annual Draft | 2B+ | Terrin | Vavra | MLB |
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| 10 | 15 | 231 | 2023 | Annual Draft | P | Hunter | Gaddis | MLB |
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| 1 | 18 | 18 | 2022 | 28 Man Draft | OF+ | Jorge | Mateo | MLB |
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| 1 | 18 | 18 | 2022 | Annual Draft | P | Tylor | Megill | MLB |
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| 2 | 19 | 43 | 2022 | Annual Draft | 1B | Ivan | Melendez | COL |
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| 2 | 19 | 43 | 2022 | 28 Man Draft | 2B+ | Wilmer | Difo | MLB |
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| 3 | 18 | 66 | 2022 | 28 Man Draft | P | Zack | Britton | MLB |
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| 3 | 18 | 66 | 2022 | Annual Draft | 2B+ | Andy | Ibanez | MLB |
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| 4 | 19 | 91 | 2022 | Annual Draft | OF | Yadiel | Hernandez | MLB |
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| 5 | 18 | 114 | 2022 | Annual Draft | P | Tyler | Gilbert | MLB |
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| 6 | 19 | 139 | 2022 | Annual Draft | P | Deolis | Guerra | MLB |
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| 7 | 18 | 162 | 2022 | Annual Draft | SS+ | Sergio | Alcantara | MLB |
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| 8 | 19 | 187 | 2022 | Annual Draft | OF+ | Jake | Bauers | MLB |
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| 9 | 18 | 210 | 2022 | Annual Draft | 1B+ | Taylor | Jones | MLB |
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| 10 | 19 | 235 | 2022 | Annual Draft | C | Tres | Barrera | MLB |
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| 1 | 7 | 7 | 2021 | Annual Draft | 3B | Alec | Bohm | MLB |
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| 1 | 7 | 7 | 2021 | 28 Man Draft | P | A.J. | Cole | MLB |
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| 2 | 7 | 31 | 2021 | 28 Man Draft | P | Adam | Ottavino | MLB |
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| 2 | 7 | 31 | 2021 | Annual Draft | P | Tejay | Antone | MLB |
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| 3 | 7 | 55 | 2021 | Annual Draft | SP | Jack | Leiter | COL |
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| 3 | 7 | 55 | 2021 | 28 Man Draft | P | Carson | Fulmer | MLB |
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| 4 | 7 | 79 | 2021 | Annual Draft | 2B | Ha-Seong | Kim | OS |
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| 4 | 22 | 94 | 2021 | Annual Draft | P | Taylor | Clarke | MLB |
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| 5 | 7 | 103 | 2021 | Annual Draft | P | Ryan | Castellani | MLB |
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| 6 | 7 | 127 | 2021 | Annual Draft | P | Bruce | Zimmermann | MLB |
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| 7 | 7 | 151 | 2021 | Annual Draft | P | Jake | Woodford | MLB |
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| 8 | 7 | 175 | 2021 | Annual Draft | SS+ | Ronald | Torreyes | MLB |
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| 9 | 7 | 199 | 2021 | Annual Draft | P | Nabil | Crismatt | MLB |
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| 1 | 4 | 4 | 2020 | 28 Man Draft | OF | Wil | Myers | MLB |
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| 2 | 4 | 28 | 2020 | 28 Man Draft | C | John | Hicks | MLB |
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| 2 | 4 | 28 | 2020 | Annual Draft | OF | Mike | Yastrzemski | MLB |
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| 3 | 4 | 52 | 2020 | Annual Draft | P | Jordan | Yamamoto | MLB |
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| 3 | 4 | 52 | 2020 | 28 Man Draft | OF | Yairo | Munoz | MLB |
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| 4 | 4 | 76 | 2020 | Annual Draft | P | Logan | Webb | MLB |
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| 5 | 4 | 100 | 2020 | Annual Draft | P | Dario | Agrazal | MLB |
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| 6 | 4 | 124 | 2020 | Annual Draft | P | Peter | Lambert | MLB |
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| 7 | 4 | 148 | 2020 | Annual Draft | P | Nick | Ramirez | MLB |
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| 8 | 4 | 172 | 2020 | Annual Draft | C | Cam | Gallagher | MLB |
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| 9 | 4 | 196 | 2020 | Annual Draft | P | Javy A. | Guerra | MLB |
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| 10 | 4 | 220 | 2020 | Annual Draft | P | Adrian | Sampson | MLB |
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| 1 | 5 | 5 | 2019 | Rookie Draft | SP | Brad | Keller | MLB |
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| 2 | 5 | 29 | 2019 | Rookie Draft | SP | Ryan | Yarbrough | MLB |
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| 3 | 5 | 53 | 2019 | Rookie Draft | OF | Jake | Cave | MLB |
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| 4 | 5 | 77 | 2019 | Rookie Draft | SP | Sam | Gaviglio | MLB |
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| 5 | 5 | 101 | 2019 | Rookie Draft | SP | Cal | Quantrill | MIN |
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| 6 | 5 | 125 | 2019 | Rookie Draft | 3B | Ty | France | MIN |
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| 7 | 5 | 149 | 2019 | Rookie Draft | SP | Kohl | Stewart | MLB |
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| 8 | 5 | 173 | 2019 | Rookie Draft | C | Jose | Briceno | MLB |
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| 9 | 5 | 197 | 2019 | Rookie Draft | 1B | Jim | Adduci | MLB |
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| 10 | 5 | 221 | 2019 | Rookie Draft | 2B | Gregorio | Petit | MLB |
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| 1 | 11 | 11 | 2018 | Rookie Draft | OF | Franchy | Cordero | MLB |
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| 2 | 11 | 35 | 2018 | Rookie Draft | OF | Willie | Calhoun | MLB |
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| 3 | 11 | 59 | 2018 | Rookie Draft | 3B | Christian | Arroyo | MLB |
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| 4 | 11 | 83 | 2018 | Rookie Draft | 3B | Yandy | Diaz | MLB |
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| 5 | 11 | 107 | 2018 | Rookie Draft | SP | Erick | Fedde | MLB |
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| 6 | 11 | 131 | 2018 | Rookie Draft | C | Luis | Torrens | MLB |
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| 6 | 16 | 136 | 2018 | Rookie Draft | RP | Chris | O'Grady | MLB |
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| 7 | 11 | 155 | 2018 | Rookie Draft | OF | Anthony | Santander | MLB |
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| 7 | 16 | 160 | 2018 | Rookie Draft | C | Raudy | Read | MLB |
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| 8 | 11 | 179 | 2018 | Rookie Draft | SP | Miguel | Diaz | MLB |
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| 9 | 11 | 203 | 2018 | Rookie Draft | SP | Felix | Jorge | MLB |
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| 10 | 11 | 227 | 2018 | Rookie Draft | RP | Ronald | Herrera | MLB |
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| 1 | 12 | 12 | 2017 | Rookie Draft | 3B | Ryon | Healy | MLB |
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| 2 | 12 | 36 | 2017 | Rookie Draft | OF | Albert | Almora | MLB |
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| 3 | 12 | 60 | 2017 | Rookie Draft | OF | Joey | Rickard | MLB |
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| 4 | 12 | 84 | 2017 | Rookie Draft | RP | Ryan | Buchter | MLB |
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| 5 | 12 | 108 | 2017 | Rookie Draft | SP | Braden | Shipley | MLB |
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| 6 | 12 | 132 | 2017 | Rookie Draft | SP | Luis | Cessa | MLB |
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| 7 | 12 | 156 | 2017 | Rookie Draft | SP | Paul | Clemens | MLB |
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| 8 | 12 | 180 | 2017 | Rookie Draft | SP | Matt | Cain | MLB |
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| 9 | 12 | 204 | 2017 | Rookie Draft | SS | Luis | Urias | MIN |
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| 10 | 12 | 228 | 2017 | Rookie Draft | SP | Adrian | Morejon | MIN |
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| 1 | 11 | 11 | 2016 | Rookie Draft | OF | Eddie | Rosario | MLB |
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| 2 | 10 | 34 | 2016 | Rookie Draft | 1B | Mark | Canha | MLB |
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| 2 | 16 | 40 | 2016 | Rookie Draft | OF | Preston | Tucker | MLB |
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| 3 | 11 | 59 | 2016 | Rookie Draft | RP | Felipe | Rivero | MLB |
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| 4 | 10 | 82 | 2016 | Rookie Draft | SP | Adam | Morgan | MLB |
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| 5 | 11 | 107 | 2016 | Rookie Draft | RP | Alex | Meyer | MLB |
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| 6 | 10 | 130 | 2016 | Rookie Draft | RP | Miguel | Almonte | MLB |
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| 7 | 11 | 155 | 2016 | Rookie Draft | SP | Brian | Johnson | MLB |
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| 8 | 10 | 178 | 2016 | Rookie Draft | 2B | Ryan | Brett | MLB |
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| 9 | 11 | 203 | 2016 | Rookie Draft | 2B | Yulieski | Gourriel | OS |
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| 10 | 10 | 226 | 2016 | Rookie Draft | OF | Mallex | Smith | MIN |
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| 1 | 9 | 9 | 2015 | Rookie Draft | OF | Randal | Grichuk | MLB |
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| 1 | 19 | 19 | 2015 | Rookie Draft | SP | Odrisamer | Despaigne | MLB |
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| 2 | 11 | 35 | 2015 | Rookie Draft | SP | David | Buchanan | MLB |
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| 3 | 9 | 57 | 2015 | Rookie Draft | 2B | Matt | Duffy | MLB |
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| 6 | 11 | 131 | 2015 | Rookie Draft | RP | Matt | Barnes | MLB |
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| 7 | 9 | 153 | 2015 | Rookie Draft | 1B | Kyle | Parker | MLB |
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| 8 | 11 | 179 | 2015 | Rookie Draft | RP | Edwin | Escobar | MLB |
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| 9 | 9 | 201 | 2015 | Rookie Draft | RP | Wei-Chung | Wang | MLB |
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| 10 | 11 | 227 | 2015 | Rookie Draft | OF | Bryce | Brentz | MLB |
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| 1 | 6 | 6 | 2014 | Rookie Draft | SP | Alex | Wood | MLB |
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| 1 | 11 | 11 | 2013 | Rookie Draft | 1B | Jose | Abreu | OS |
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| 2 | 11 | 35 | 2013 | Rookie Draft | RP | David | Phelps | MLB |
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| 3 | 11 | 59 | 2013 | Rookie Draft | RP | Ronald | Belisario | MLB |
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| 4 | 11 | 83 | 2013 | Rookie Draft | RP | Jeurys | Familia | MLB |
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| 5 | 11 | 107 | 2013 | Rookie Draft | RP | Nick | Maronde | MLB |
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| 6 | 11 | 131 | 2013 | Rookie Draft | SP | Jeremy | Hefner | MLB |
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| 7 | 11 | 155 | 2013 | Rookie Draft | SP | Mark | Rogers | MLB |
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| 8 | 11 | 179 | 2013 | Rookie Draft | C | Jhonatan | Solano | MLB |
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| 9 | 11 | 203 | 2013 | Rookie Draft | C | Sandy | Leon | MLB |
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| 10 | 11 | 227 | 2013 | Rookie Draft | SS | Carlos | Triunfel | MLB |
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| 1 | 16 | 16 | 2012 | Rookie Draft | P | Anthony | Bass | MLB |
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| 2 | 16 | 40 | 2012 | Rookie Draft | 3B | Jimmy | Paredes | MLB |
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| 3 | 16 | 64 | 2012 | Rookie Draft | 3B | Logan | Forsythe | MLB |
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| 4 | 16 | 88 | 2012 | Rookie Draft | 3B | Matt | Dominguez | MLB |
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| 5 | 16 | 112 | 2012 | Rookie Draft | P | Tim | Wakefield | MLB |
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| 6 | 16 | 136 | 2012 | Rookie Draft | P | Nate | Adcock | MLB |
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| 7 | 16 | 160 | 2012 | Rookie Draft | P | Fernando | Rodriguez | MLB |
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| 8 | 16 | 184 | 2012 | Rookie Draft | P | Kyle | Weiland | MLB |
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| 9 | 16 | 208 | 2012 | Rookie Draft | 2B | Cory | Spangenberg | MIN |
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| 10 | 16 | 232 | 2012 | Rookie Draft | P | Chris | Jakubauskas | MLB |
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| 1 | 10 | 10 | 2011 | Rookie Draft | RP | Jonny | Venters | MLB |
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| 2 | 10 | 34 | 2011 | Rookie Draft | 1B | Anthony | Rizzo | MIN |
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| 3 | 10 | 58 | 2011 | Rookie Draft | SP | Tyson | Ross | MLB |
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| 4 | 10 | 82 | 2011 | Rookie Draft | 2B | Matt | Downs | MLB |
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| 5 | 10 | 106 | 2011 | Rookie Draft | RP | Daniel | Moskos | MIN |
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| 6 | 10 | 130 | 2011 | Rookie Draft | SS | Yamaico | Navarro | MLB |
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| 7 | 10 | 154 | 2011 | Rookie Draft | SS | Andrew | Romine | MLB |
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| 7 | 22 | 166 | 2011 | Rookie Draft | OF | Darren | Ford | MLB |
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| 8 | 10 | 178 | 2011 | Rookie Draft | OF | Brandon | Boggs | MLB |
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| 9 | 10 | 202 | 2011 | Rookie Draft | OF | Colin | Curtis | MLB |
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| 10 | 10 | 226 | 2011 | Rookie Draft | OF | Cole | Gillespie | MLB |
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| 1 | 12 | 12 | 2010 | Rookie Draft | RP | Luke | Gregerson | MLB |
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| 2 | 12 | 36 | 2010 | Rookie Draft | RP | Sean | White | MLB |
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| 3 | 12 | 60 | 2010 | Rookie Draft | SS | Ramiro | Pena | MLB |
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| 4 | 12 | 84 | 2010 | Rookie Draft | OF | Luis | Durango | MLB |
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| 5 | 12 | 108 | 2010 | Rookie Draft | C | Hank | Conger | MIN |
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| 6 | 12 | 132 | 2010 | Rookie Draft | RP | Chris | Jakubauskas | MLB |
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| 7 | 12 | 156 | 2010 | Rookie Draft | 2B | Edwin | Maysonet | MLB |
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| 8 | 12 | 180 | 2010 | Rookie Draft | OF | Trent | Oeltjen | MLB |
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| 9 | 12 | 204 | 2010 | Rookie Draft | RP | Ernesto | Frieri | MLB |
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| 10 | 12 | 228 | 2010 | Rookie Draft | 1B | Jesus | Guzman | MLB |
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| 1 | 14 | 14 | 2009 | Rookie Draft | C | John | Baker | MLB |
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| 2 | 14 | 38 | 2009 | Rookie Draft | 1B | John | Bowker | MLB |
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| 3 | 14 | 62 | 2009 | Rookie Draft | 3B | Conor | Gillaspie | MLB |
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| 4 | 14 | 86 | 2009 | Rookie Draft | SS | Everth | Cabrera | MIN |
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| 5 | 14 | 110 | 2009 | Rookie Draft | 3B | Jeff | Larish | MLB |
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| 6 | 14 | 134 | 2009 | Rookie Draft | 1B | Oscar | Salazar | MLB |
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| 7 | 14 | 158 | 2009 | Rookie Draft | 1B | Kila | Kaaihue | MLB |
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| 8 | 14 | 182 | 2009 | Rookie Draft | 3B | Pete | Orr | MLB |
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| 9 | 14 | 206 | 2009 | Rookie Draft | 1B | Randy | Ruiz | MLB |
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| 10 | 14 | 230 | 2009 | Rookie Draft | 3B | Jeff | Baisley | MLB |
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Windy City Hit Men (WIN), 9999 - 9999
