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| Sunday, August 9th, 2020 |
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| Failed to sign 1st round draft pick Robert Hassell III. |
| Failed to sign 2nd round draft pick Trei Cruz. |
| Failed to sign 3rd round draft pick Seth Lonsway. |
| Failed to sign 4th round draft pick Nate Wohlgemuth. |
| Failed to sign 5th round draft pick Brady Smith. |
| Failed to sign 10th round draft pick George Klassen. |
| Thursday, August 6th, 2020 |
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| Placed LF Kyle Schwarber on the 60-day injured list. |
| Placed 2B Jonathan Villar on the active roster. |
| Thursday, July 30th, 2020 |
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| Traded 20-year-old minor league starting pitcher Kohl Franklin to the Miami Marlins, getting 29-year-old second baseman Jonathan Villar in return. |
| Assigned RP Casey Sadler to Triple A Iowa. |
| Thursday, July 23rd, 2020 |
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| Optioned C Miguel Amaya to Triple A Iowa. |
| Purchased the contract of C Josh Phegley from Triple A Iowa. |
| RP Casey Sadler was designated for assignment and placed on waivers. |
| Placed SP Steven Matz on the active roster. |
| Thursday, July 16th, 2020 |
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| Optioned CF Ian Miller to Triple A Iowa. |
| Placed RF Jason Heyward on the active roster. |
| Activated RF Jason Heyward from the injured list. |
| Placed RP Casey Sadler on irrevocable waivers. |
| Optioned RP Kyle Ryan to Triple A Iowa. |
| Placed SP Jon Lester on the active roster. |
| Traded 26-year-old catcher Victor Caratini to the New York Mets, getting 29-year-old starting pitcher Steven Matz in return. |
| Purchased the contract of C Miguel Amaya from Double A Tennessee. |
| Thursday, June 18th, 2020 |
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| Optioned 2B Zack Short to Triple A Iowa. |
| Purchased the contract of RP Casey Sadler from Triple A Iowa. |
| Thursday, June 11th, 2020 |
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| Placed RF Jason Heyward on the 10-day injured list, retroactive to 06/09/2020. |
| Placed RF Steven Souza Jr. on the 10-day injured list, retroactive to 06/05/2020. |
| Sent SP Jon Lester to Triple A Iowa for injury rehab. |
| Purchased the contract of 2B Zack Short from Triple A Iowa. |
| Purchased the contract of CF Ian Miller from Triple A Iowa. |
| Traded 31-year-old starting pitcher Jose Quintana to the Houston Astros, getting 33-year-old left fielder Michael Brantley in return. |
| Placed LF Michael Brantley on the active roster. |
| Wednesday, June 10th, 2020 |
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| Transferred SP Justin Steele to the 60-day IL. |
| Thursday, May 28th, 2020 |
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| Placed SP Jon Lester on the 15-day injured list, retroactive to 05/26/2020. |
| Purchased the contract of SP Adbert Alzolay from Triple A Iowa. |
| Received former Rule 5 draft pick2B Vimael Machin from the Oakland Athletics. |
| Traded 26-year-old second baseman Vimael Machin to the Oakland Athletics, getting 26-year-old minor league reliever Zack Erwin in return. |
| Assigned 2B Daniel Descalso to Triple A Iowa. |
| Thursday, May 21st, 2020 |
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| Placed RP Brandon Morrow on the 15-day injured list, retroactive to 05/20/2020. |
| Purchased the contract of RF Steven Souza Jr. from Triple A Iowa. |
| 2B Daniel Descalso was designated for assignment and placed on waivers. |
| Purchased the contract of RP Kyle Ryan from Double A Tennessee. |
| Thursday, May 7th, 2020 |
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| Sent RF Steven Souza Jr. to Triple A Iowa for injury rehab. |
| Thursday, April 23rd, 2020 |
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| Assigned RP Colin Rea to Triple A Iowa. |
| Thursday, April 9th, 2020 |
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| Demoted RP Jose Alcila to Low-A Eugene. |
| Wednesday, April 1st, 2020 |
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| Assigned 2B Hernan Perez to Triple A Iowa. |
