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| Monday, September 16th, 2019 |
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| Placed RP Adam Warren on the 10-day injured list, retroactive to 09/13/2019. |
| Placed SP Tyler Mahle on the 10-day injured list, retroactive to 09/08/2019. |
| Sunday, September 1st, 2019 |
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| Purchased the contract of 1B Brent Rooker from Triple A Indianapolis. |
| Purchased the contract of RP Fernando Romero from Triple A Indianapolis. |
| Purchased the contract of RP Gerson Moreno from Triple A Indianapolis. |
| Purchased the contract of SP Tyler Mahle from Triple A Indianapolis. |
| Purchased the contract of LF Billy McKinney from Triple A Indianapolis. |
| Purchased the contract of CF Forrest Wall from Triple A Indianapolis. |
| Thursday, July 25th, 2019 |
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| Optioned LF Billy McKinney to Triple A Indianapolis. |
| Placed CF LaMonte Wade on the active roster. |
| Sunday, July 21st, 2019 |
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| Placed RP Jonathan Loaisiga on the active roster. |
| Saturday, July 20th, 2019 |
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| Traded 32-year-old left fielder Andrew McCutchen to the Baltimore Orioles, getting 24-year-old minor league starting pitcher Jonathan Loaisiga, 20-year-old minor league catcher Miguel Amaya and 25-year-old minor league center fielder LaMonte Wade in return. |
| Monday, July 8th, 2019 |
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| Placed RP Jace Fry on the 60-day injured list. |
| Purchased the contract of RP Devan Watts from Triple A Indianapolis. |
| Wednesday, June 19th, 2019 |
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| Placed SP Patrick Corbin on the active roster. |
| Activated SP Patrick Corbin from the injured list. |
| Tuesday, June 18th, 2019 |
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| Traded 24-year-old shortstop Carlos Correa to the Minnesota Twins, getting 23-year-old minor league third baseman Bobby Dalbec, 18-year-old minor league right fielder Kristian Robinson and 18-year-old minor league starting pitcher Simeon Woods-Richardson in return. |
| Monday, June 3rd, 2019 |
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| Placed SP Patrick Corbin on the 10-day injured list, retroactive to 05/22/2019. |
| Purchased the contract of RP Matt Bush from Triple A Indianapolis. |
| Thursday, March 21st, 2019 |
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| RP Trevor May was claimed off waivers from Milwaukee. |
| Optioned RP Matt Bush to Triple A Indianapolis. |
| Placed RP Trevor May on the active roster. |
| Wednesday, March 20th, 2019 |
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| Purchased the contract of RP Matt Bush from Triple A Indianapolis. |
| Tuesday, March 19th, 2019 |
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| SP Tyson Ross was designated for assignment and placed on waivers. |
| Optioned CF Forrest Wall to Triple A Indianapolis. |
| Optioned RP Matt Bush to Triple A Indianapolis. |
| Optioned SP Taylor Hearn to Triple A Indianapolis. |
| Sunday, March 17th, 2019 |
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| Assigned 1B Brent Rooker from Spring Training camp to Triple A Indianapolis. |
| Optioned RP Fernando Romero to Triple A Indianapolis. |
| Optioned CL Devan Watts to Triple A Indianapolis. |
| Friday, March 15th, 2019 |
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| Purchased the contract of SP Taylor Hearn from Triple A Indianapolis. |
| Invited non-roster SP Bernardo Flores to Spring Training camp. |
| Invited non-roster SP Dakota Chalmers to Spring Training camp. |
| Invited non-roster RP Michel Baez to Spring Training camp. |
| Tuesday, March 5th, 2019 |
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| Optioned RP Gerson Moreno to Triple A Indianapolis. |
| Optioned CF Forrest Wall to Triple A Indianapolis. |
| Optioned LF Telmito Agustin to Double A Altoona. |
| Optioned 1B Emmanuel Tapia to Triple A Indianapolis. |
| Invited non-roster 3B Hudson Potts to Spring Training camp. |
| Invited non-roster 2B Daniel Brito to Spring Training camp. |
| Invited non-roster 1B Brent Rooker to Spring Training camp. |
| Purchased the contract of CF Forrest Wall from Triple A Indianapolis. |
| Saturday, February 23rd, 2019 |
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| Optioned C Zack Collins to Triple A Indianapolis. |
| Optioned SP Patrick Weigel to Triple A Indianapolis. |
| Optioned SP Taylor Hearn to Triple A Indianapolis. |
| Thursday, February 14th, 2019 |
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| Signed free agent 2B Jason Kipnis to a 2-year contract worth a total of $19,000,000. |
| Placed 2B Jason Kipnis on the active roster. |
| Wednesday, February 13th, 2019 |
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| Sent LF Billy McKinney to Major League New York. |
| Received LF Billy McKinney from Major League New York. |
| Purchased the contract of C Zack Collins from Triple A Indianapolis. |
| Purchased the contract of CL Devan Watts from Triple A Indianapolis. |
| Purchased the contract of RP Fernando Romero from Triple A Indianapolis. |
| Purchased the contract of SP Taylor Hearn from Triple A Indianapolis. |
| Purchased the contract of CF Forrest Wall from Triple A Indianapolis. |
| Purchased the contract of LF Telmito Agustin from Double A Altoona. |
| Purchased the contract of 1B Emmanuel Tapia from Triple A Indianapolis. |
| Purchased the contract of SP Patrick Weigel from Double A Altoona. |
| Purchased the contract of 1B Bobby Bradley from Triple A Indianapolis. |
| Purchased the contract of RP Gerson Moreno from Triple A Indianapolis. |
| Tuesday, February 5th, 2019 |
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| Traded 31-year-old right fielder Jay Bruce to the Minnesota Twins, getting 21-year-old minor league third baseman Jean Carlos Encarnacion and 23-year-old minor league starting pitcher Michel Baez in return. |
| Sunday, February 3rd, 2019 |
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| Purchased the contract of 3B Renato Nunez from Triple A Indianapolis. |
| Purchased the contract of LF Billy McKinney from Triple A Indianapolis. |
| Friday, February 1st, 2019 |
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| Purchased the contract of C Josh Phegley from Triple A Indianapolis. |
| Wednesday, January 30th, 2019 |
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| Signed free agent RP Adam Ottavino to a 2-year contract worth a total of $25,000,000. |
| Signed free agent SP Martin Perez to a 5-year contract worth a total of $42,500,000. |
| Tuesday, January 29th, 2019 |
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| Signed free agent RF Andrew McCutchen to a 4-year contract worth a total of $112,000,000. |
| Friday, January 4th, 2019 |
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| Placed RP Adam Warren on the active roster. |
