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| Thursday, December 19th , 2019 |
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| Traded 25-year old minor league 3B Matt Boyd to the Atlanta Pilots, getting 28-year old LHP Alex Perez in return. |
| Placed SP Alex Perez on the active roster. |
| Wednesday, December 11th , 2019 |
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| Placed SS Chris Phillips on the active roster. |
| Placed SS Chris Phillips on the active roster. |
| Lost SP Miguel Hernandez in the Rule 5 Draft to the Philadelphia Keystones. |
| Saturday, December 7th , 2019 |
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| Signed free agent SS Chris Phillips to a 5-year contract worth a total of $7,000,000. |
| Wednesday, November 27th , 2019 |
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| LF Justin Freeman was designated for assignment and placed on waivers. |
| Purchased the contract of C Tony McLaughlin from Triple A Montreal. |
| Tuesday, November 19th , 2019 |
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| SS Chris Phillips becomes a free-agent. |
| LF Jon Dozier received a 1-year contract through automatic renewal worth a total of $100,000. |
| SP Brian Fistler received a 1-year contract through automatic renewal worth a total of $100,000. |
| 2B Willie Rodriguez received a 1-year contract through automatic renewal worth a total of $100,000. |
| CF Matt Kelly received a 1-year contract through automatic renewal worth a total of $100,000. |
| RP Ben Craig received a 1-year contract through automatic renewal worth a total of $100,000. |
| SP Ron Clous becomes a free-agent. |
| RP Jonathan Benders becomes a free-agent. |
| 3B Gary Payer becomes a free-agent. |
| RF Torjus Rasmussen received a 1-year contract through automatic renewal worth a total of $100,000. |
| 1B Jon Witt received a 1-year contract through automatic renewal worth a total of $100,000. |
| C Paolo van Bragt received a 1-year contract through automatic renewal worth a total of $100,000. |
| RP Tyler Anson received a 1-year contract through automatic renewal worth a total of $100,000. |
| 2B Andres Martinez received a 1-year contract through automatic renewal worth a total of $100,000. |
| 1B Eddie Caballero received a 1-year contract through automatic renewal worth a total of $100,000. |
| RP Bob James becomes a free-agent. |
| RP Brian Phillips received a 1-year contract through automatic renewal worth a total of $100,000. |
| SS Robert Carrillo received a 1-year contract through automatic renewal worth a total of $100,000. |
| 1B Adolfo Milagres received a 1-year contract through automatic renewal worth a total of $100,000. |
| SP Javier Mata received a 1-year contract through automatic renewal worth a total of $100,000. |
| CL Quincy Brooks received a 1-year contract through automatic renewal worth a total of $100,000. |
| RP Mikael Öunap received a 1-year contract through automatic renewal worth a total of $100,000. |
| 2B Samppa Lehtola received a 1-year contract through automatic renewal worth a total of $100,000. |
| C Bob Ortega received a 1-year contract through automatic renewal worth a total of $100,000. |
| SP Jaheim Kinney received a 1-year contract through automatic renewal worth a total of $100,000. |
| SS Matt Blair received a 1-year contract through automatic renewal worth a total of $100,000. |
| Assigned 3B Kelvin Tillman to Triple A Montreal. |
| Assigned RF Aaron Tabron to Triple A Montreal. |
| Wednesday, November 13th , 2019 |
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| Assigned LF Sidney Botequim to Double A Ottawa. |
| Assigned 3B Mike Daniel to Double A Ottawa. |
| Sunday, November 3rd , 2019 |
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| Signed Assistant GM Christian Mullen to a 3-year, $42,500 per year contract. |
| Wednesday, October 30th , 2019 |
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| Assistant GM Luis Maldonado leaves the team, his contract was not renewed |
| Executed the contract year option of SP Jurg van Gelderen. |
| Executed the contract year option of RP Chris McCarty. |
| RF Aaron Tabron was designated for assignment and placed on waivers. |
| Saturday, October 19th , 2019 |
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| Signed Scouting Director Joel Jackson to a 4-year contract extension. |
| Signed Pitching Coach Kevin Tilley to a 4-year contract extension. |
| Assigned LF Nick Beckwith to Double A Ottawa. |
| Wednesday, October 9th , 2019 |
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| Optioned 2B Willie Rodriguez to Triple A Montreal. |
| Placed 1B Adolfo Milagres on the active roster. |
| Activated 1B Adolfo Milagres from the injured list. |
| Friday, September 27th , 2019 |
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| Assigned 2B Burkhard Peters to Double A Ottawa. |
| Assigned RF Jaheim Richardson to Double A Ottawa. |
| Tuesday, September 17th , 2019 |
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| Assigned CF Jayson Dawkins to Double A Ottawa. |
| Thursday, September 12th , 2019 |
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| Placed 1B Adolfo Milagres on the 10-day injured list, retroactive to 09/09/2019. |
| Purchased the contract of 2B Willie Rodriguez from Triple A Montreal. |
| Assigned 2B Josh Bass to Triple A Montreal. |
| Assigned RF Ken Cantrell to Double A Ottawa. |
| Monday, September 2nd , 2019 |
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| Optioned 2B Willie Rodriguez to Triple A Montreal. |
| Purchased the contract of 2B Andres Martinez from Triple A Montreal. |
| Monday, August 26th , 2019 |
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| Assigned 3B Mike Daniel to Triple A Montreal. |
| Assigned LF Nick Beckwith to Double A Ottawa. |
| Assigned LF John Hoffman to Triple A Montreal. |
| Wednesday, August 21st , 2019 |
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| Optioned RP Chris McCarty to Triple A Montreal. |
| Purchased the contract of SP Jaheim Kinney from Triple A Montreal. |
| Assigned RP Juan Navarrete to Double A Ottawa. |
| Friday, August 16th , 2019 |
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| Assigned 2B Josh Bass to Triple A Montreal. |
| Assigned RF Ken Cantrell to Double A Ottawa. |
| Assigned RF Ryan Hubbard to Double A Ottawa. |
| Sunday, August 11th , 2019 |
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| Assigned 1B Matt Nailer to Triple A Montreal. |
| Tuesday, August 6th , 2019 |
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| Assigned SP Josh Little to Double A Ottawa. |
| Assigned SS Miguel Salinas to Double A Ottawa. |
| Thursday, August 1st , 2019 |
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| Assigned LF Sidney Botequim to Double A Ottawa. |
| Assigned 1B Xi-tong Zhào to Triple A Montreal. |
| Assigned C Adri van Heijningen to Double A Ottawa. |
| Saturday, July 27th , 2019 |
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| Assigned LF John Hoffman to Triple A Montreal. |
| Assigned 3B Kelvin Tillman to Triple A Montreal. |
| Assigned RP Steven Payton to Double A Ottawa. |
| Optioned RP Brian Fistler to Triple A Montreal. |
| Assigned C Isaac Cherry to Triple A Montreal. |
| Traded 23-year old minor league RHP Jon Johnson to the Washington Warriors, getting 18-year old minor league SS Jake Faltersack, 39-year old RHP Ron Clous (retaining 40%), and 20-year old minor league LHP Jesus Garcia in return. |
| Placed SP Ron Clous on the active roster. |
| Thursday, July 25th , 2019 |
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| SP Garrett Seiter was claimed off waivers by San Francisco. |
| Wednesday, July 17th , 2019 |
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| Assigned 3B Matt Boyd to Triple A Montreal. |
| Assigned 2B Burkhard Peters to Double A Ottawa. |
| Assigned C Jake Quellhorst to Double A Ottawa. |
| RP Garrett Seiter was designated for assignment and placed on waivers. |
| Assigned RP Davin Fairley to Triple A Montreal. |
| Assigned RP Chris Miller to Triple A Montreal. |
| Assigned LF Omar Calderon to Double A Ottawa. |
| Assigned SS Yury Adigamoff to Double A Ottawa. |
| Friday, July 12th , 2019 |
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| Assigned 1B Matt Nailer to Triple A Montreal. |
| Assigned RF Rich Guardiola to Triple A Montreal. |
| Assigned RF Ryan Hubbard to Double A Ottawa. |
| Tuesday, July 2nd , 2019 |
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| Traded 18-year old minor league RHP Sal Buitrago to the El Paso Diablos, getting 25-year old minor league RHP Brian Fistler in return. |
| Thursday, June 27th , 2019 |
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| Assigned RP Ben Craig to Triple A Montreal. |
| Assigned SS Yury Adigamoff to Double A Ottawa. |
| Saturday, June 22nd , 2019 |
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| Assigned SP Danny Gipson to Triple A Montreal. |
| Assigned LF Nick Beckwith to Double A Ottawa. |
| Assigned 2B Isaac Birkbeck to Double A Ottawa. |
| Assigned 1B Robby Barrera to Triple A Montreal. |
| Assigned RP Conrad Foster to Triple A Montreal. |
| Assigned RP Davin Fairley to Triple A Montreal. |
| Assigned 2B Burkhard Peters to Double A Ottawa. |
| Assigned LF Théo Coulon to Triple A Montreal. |
| Optioned SS Robert Carrillo to Triple A Montreal. |
| Placed 3B Gary Payer on the active roster. |
| Activated 3B Gary Payer from the injured list. |
| Assigned RF Ryan Hubbard to Double A Ottawa. |
| Assigned 3B Kelvin Tillman to Triple A Montreal. |
| Traded 25-year old RHP Tyshawn Dortch and 24-year old minor league RHP Peter Auman to the Denver Cutthroats, getting 19-year old minor league SS Erhard Miller and $500,000 in cash in return. |
| Recalled SP Mikael Öunap from Triple A Montreal. |
| Thursday, June 20th , 2019 |
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| 2B Jurg Gorbatsevich was claimed off waivers by Boston. |
| Monday, June 17th , 2019 |
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| Traded 20-year old minor league RHP Jon Lowers and 21-year old minor league CF Jonah Cotton to the Houston Mavericks, getting $1,400,000 in cash in return. |
| Wednesday, June 12th , 2019 |
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| RP Conrad Foster was designated for assignment and placed on waivers. |
| Traded 24-year old minor league CF Bob Guaman and 22-year old minor league 2B Bobby Stern to the Chicago Union, getting 26-year old RHP Javier Mata in return. |
| Placed SP Javier Mata on the active roster. |
| Monday, May 27th , 2019 |
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| Placed SP Bob James on the active roster. |
| Invited non-roster C Tony McLaughlin to Spring Training camp. |
| Placed RP Garrett Seiter on the 10-day injured list, retroactive to 05/24/2019. |
| RP Miguel Hernandez was designated for assignment and placed on waivers. |
| Optioned CF Bob Guaman to Triple A Montreal. |
| Optioned 1B Jon Witt to Triple A Montreal. |
| Assigned 2B Marc Capone from Spring Training camp to Double A Ottawa. |
| Assigned RP Jaheim Kinney from Spring Training camp to Double A Ottawa. |
| Optioned SP Mikael Öunap to Triple A Montreal. |
| Assigned LF Bruce Bogan from Spring Training camp to Double A Ottawa. |
| Assigned RF Rich Guardiola from Spring Training camp to Triple A Montreal. |
| Optioned RF Aaron Tabron to Triple A Montreal. |
| Placed 3B Gary Payer on the 10-day injured list, retroactive to 05/25/2019. |
| Optioned 1B Robby Barrera to Triple A Montreal. |
| Tuesday, May 14th , 2019 |
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| Assigned RP Micah Young from Spring Training camp to Triple A Montreal. |
| Optioned RP Peter Auman to Triple A Montreal. |
| Traded 19-year old minor league RF Marco Becerra to the Atlanta Pilots, getting 29-year old RHP Bob James in return. |
| Wednesday, May 1st , 2019 |
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| Purchased the contract of RP Adrian Denning from Triple A Montreal. |
| Purchased the contract of CF Bob Guaman from Double A Ottawa. |
| Purchased the contract of SP Peter Auman from Triple A Montreal. |
| Purchased the contract of LF Jon Dozier from Triple A Montreal. |
| Purchased the contract of SP Danny Gipson from Triple A Montreal. |
| Purchased the contract of SP Garrett Seiter from Triple A Montreal. |
| Purchased the contract of SS Matt Blair from Triple A Montreal. |
| Purchased the contract of 1B Jon Witt from Triple A Montreal. |
| Purchased the contract of 3B Samppa Lehtola from Triple A Montreal. |
| Purchased the contract of SS Robert Carrillo from Advanced Prospect League Hamilton. |
| Purchased the contract of 2B Adolfo Milagres from Triple A Montreal. |
| Purchased the contract of SP Mikael Öunap from Triple A Montreal. |
| Placed RP Quincy Brooks on the active roster. |
| Invited non-roster SP Jaheim Kinney to Spring Training camp. |
| Invited non-roster 2B Marc Capone to Spring Training camp. |
| Invited non-roster LF Bruce Bogan to Spring Training camp. |
| Invited non-roster RF Rich Guardiola to Spring Training camp. |
| Invited non-roster SP Micah Young to Spring Training camp. |
| Assigned RP Ben Craig to Triple A Montreal. |
| Traded 26-year old LHP Billy Piatt to the Las Vegas Aces, getting 20-year old minor league LHP Daniel Denny and 20-year old minor league LHP Oscar Berrios in return. |
| Traded 26-year old RHP Adrian Denning and 26-year old minor league LHP Mike Schwartz to the Dallas Texans, getting 21-year old minor league RHP Jason Harvill in return. |
| Tuesday, April 2nd , 2019 |
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| RP Perry van Kooij was claimed off waivers by El Paso. |
| Monday, April 1st , 2019 |
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| Traded 21-year old minor league LHP Alexis Hernandez to the Chicago Union, getting 25-year old LHP Quincy Brooks in return. |
| Tuesday, March 26th , 2019 |
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| Placed CL Tyler Anson on the active roster. |
| Monday, February 4th , 2019 |
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| RP Perry van Kooij was designated for assignment and placed on waivers. |
| Traded 26-year old minor league 3B Brandon Phillips and 24-year old minor league C Paul Bauer to the Dallas Texans, getting 26-year old RHP Tyler Anson in return. |
| Friday, January 4th , 2019 |
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| Assigned RP Conrad Foster to Double A Ottawa. |
