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| Thursday, September 3rd, 2020 |
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| Purchased the contract of RF Aristides Aquino from Triple A Louisville. |
| Placed LF Jesse Winker on the 60-day injured list. |
| Purchased the contract of LF Phillip Ervin from Triple A Louisville. |
| Purchased the contract of SP Tyler Mahle from Triple A Louisville. |
| Thursday, August 20th, 2020 |
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| Optioned LF Phillip Ervin to Triple A Louisville. |
| Placed RP Pedro Strop on the active roster. |
| Thursday, August 13th, 2020 |
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| RP Pedro Strop was designated for assignment and placed on waivers. |
| Purchased the contract of RP Joel Kuhnel from Double A Chattanooga. |
| Thursday, July 30th, 2020 |
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| Traded 29-year-old starting pitcher Trevor Bauer and $4,000,000 in cash to the San Diego Padres, getting 25-year-old minor league starting pitcher Cal Quantrill, 23-year-old minor league shortstop Owen Miller and 24-year-old minor league closer Javy Guerra in return. |
| Saturday, July 18th, 2020 |
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| Transferred SP Tejay Antone to the 60-day IL. |
| Thursday, July 2nd, 2020 |
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| Assigned SS Carson Tucker to Triple A Louisville. |
| Tuesday, June 30th, 2020 |
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| Signed Carson Tucker to a minor league contract with a signing bonus of $730,000. |
| Saturday, June 27th, 2020 |
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| Signed Storm Hierholzer to a minor league contract with a signing bonus of $750,000. |
| Assigned SP Storm Hierholzer to Triple A Louisville. |
| Assigned SP Bryce Jarvis to Triple A Louisville. |
| Assigned SP Christian Roa to Triple A Louisville. |
| Assigned CF Heston Kjerstad to Triple A Louisville. |
| Wednesday, June 24th, 2020 |
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| Signed Heston Kjerstad to a minor league contract with a signing bonus of $2,540,000. |
| Signed Bryce Jarvis to a minor league contract with a signing bonus of $940,000. |
| Saturday, June 20th, 2020 |
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| Signed Christian Roa to a minor league contract with a signing bonus of $3,200,000. |
| Thursday, May 14th, 2020 |
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| Traded 24-year-old minor league starting pitcher Packy Naughton and 21-year-old minor league reliever Jose Zorrilla to the San Francisco Giants, getting 34-year-old starting pitcher Johnny Cueto in return. |
| Thursday, May 7th, 2020 |
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| Optioned RF Aristides Aquino to Triple A Louisville. |
| Purchased the contract of LF Phillip Ervin from Triple A Louisville. |
