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| Sunday, July 5th, 2020 |
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| Failed to sign 1st round draft pick Jonathon Nick. |
| Failed to sign 2nd round draft pick George Winston. |
| Failed to sign 2nd round draft pick Adam Collins. |
| Failed to sign 3rd round draft pick Ricardo Alvarez. |
| Failed to sign 3rd round draft pick Sean Corum. |
| Failed to sign 4th round draft pick Jake Pocock. |
| Failed to sign 5th round draft pick Josh Johnson. |
| Failed to sign 6th round draft pick Freddy Velasques. |
| Sunday, June 21st, 2020 |
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| Placed CF Akil Baddoo on the 60-day disabled list. |
| Placed SP Yovani Gallardo on the 15-day disabled list, retroactive to 06/02/2020. |
| Placed CF Abraham Almonte on the 15-day disabled list, retroactive to 06/17/2020. |
| Placed SP Chris Sale on the 15-day disabled list, retroactive to 05/19/2020. |
| Purchased the contract of CF Kwang-Min Kwon from Triple A Bridgeport. |
| Purchased the contract of SP Michael Shawaryn from Triple A Bridgeport. |
| Purchased the contract of LF Colin Winters from Triple A Bridgeport. |
| Purchased the contract of SP Jake Elliott from Triple A Bridgeport. |
| Tuesday, April 21st, 2020 |
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| Demoted 3B Matt E. Duffy to Triple A Bridgeport. |
| Placed RP Jon Lester on the active roster. |
| Activated RP Jon Lester from the disabled list. |
| Placed SP Francisco Liriano on the 60-day disabled list. |
| Purchased the contract of RP Josh D. Fields from Triple A Bridgeport. |
| Saturday, April 18th, 2020 |
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| Demoted SP Chris Bassitt to Triple A Bridgeport. |
| Demoted RP Buddy Baumann to Triple A Bridgeport. |
| Demoted RP Mike Leake to Triple A Bridgeport. |
| Demoted LF Yoenis Cespedes to Triple A Bridgeport. |
| Friday, April 3rd, 2020 |
|---|
| Sent C Gavin Stupienski from spring training camp to Triple A Bridgeport. |
| Sent 2B Roberto Jimenez from spring training camp to Triple A Bridgeport. |
| Sent RP Gio Gonzalez from spring training camp to Triple A Bridgeport. |
| Sent RF Corey Dickerson from spring training camp to Triple A Bridgeport. |
| Sent RP Josh D. Fields from spring training camp to Triple A Bridgeport. |
| Sent SP Michael Shawaryn from spring training camp to Triple A Bridgeport. |
| Sent RP J.J. Hoover from spring training camp to Triple A Bridgeport. |
| Placed RP Jon Lester on the 15-day disabled list, retroactive to 06/10/2019. |
| Sent 3B Yosvani Bell from spring training camp to Triple A Bridgeport. |
| RP Buddy Baumann was designated for assignment and placed on waivers. |
| SP Chris Bassitt was designated for assignment and placed on waivers. |
| RP Mike Leake was designated for assignment and placed on waivers. |
| LF Yoenis Cespedes was designated for assignment and placed on waivers. |
| Saturday, February 29th, 2020 |
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| Purchased the contract of RP Josh D. Fields from Triple A Bridgeport. |
| Purchased the contract of RF Corey Dickerson from Triple A Bridgeport. |
| Saturday, February 15th, 2020 |
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| Demoted RP Josh D. Fields to Triple A Bridgeport. |
| Friday, January 31st, 2020 |
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| Signed free agent RP Josh D. Fields to a 2-year contract worth a total of $16,180,000. |
| Monday, December 23rd, 2019 |
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| Purchased the contract of SP Michael Shawaryn from Triple A Bridgeport. |
| Monday, November 25th, 2019 |
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| C Gavin Stupienski received a 1-year contract through automatic renewal worth a total of $507,500. |
| SP Yovani Gallardo received a 1-year contract through automatic renewal worth a total of $507,500. |
| 3B Matt E. Duffy received a 1-year contract through automatic renewal worth a total of $507,500. |
| 3B Yosvani Bell received a 1-year contract through automatic renewal worth a total of $507,500. |
| RP Michael Lorenzen received a 1-year contract through automatic renewal worth a total of $507,500. |
| CF Akil Baddoo received a 1-year contract through automatic renewal worth a total of $507,500. |
| SS John Devine received a 1-year contract through automatic renewal worth a total of $507,500. |
| RP Buddy Baumann received a 1-year contract through automatic renewal worth a total of $761,250. |
| SP Chris Bassitt received a 1-year contract through automatic renewal worth a total of $507,500. |
| RP Mike Leake received a 1-year contract through automatic renewal worth a total of $507,500. |
| LF Ryan Rua received a 1-year contract through automatic renewal worth a total of $507,500. |
| RF Corey Dickerson received a 1-year contract through automatic renewal worth a total of $2,940,000. |
| Friday, November 22nd, 2019 |
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| CL Craig Kimbrel received a 1-year contract through arbitration worth a total of $7,500,000. |
| RP Jon Lester received a 1-year contract through arbitration worth a total of $6,300,000. |
| CF Adam Jones was not offered arbitration, becomes a free agent. |
| CF Abraham Almonte received a 1-year contract through arbitration worth a total of $1,500,000. |
| RP Gio Gonzalez received a 1-year contract through arbitration worth a total of $10,625,000. |
| 1B Kole Calhoun was not offered arbitration, becomes a free agent. |
| RF Josh Reddick received a 1-year contract through arbitration worth a total of $4,000,000. |
| 3B Todd Frazier received a 1-year contract through arbitration worth a total of $3,740,000. |
| RP J.J. Hoover received a 1-year contract through arbitration worth a total of $800,000. |
| SP Francisco Liriano received a 1-year contract through arbitration worth a total of $4,200,000. |
| RP Jake Diekman received a 1-year contract through arbitration worth a total of $2,712,000. |
| RP Will Smith received a 1-year contract through arbitration worth a total of $4,750,000. |
| 2B Roberto Jimenez received a 1-year contract through arbitration worth a total of $761,250. |
| RP Tony Watson received a 1-year contract through arbitration worth a total of $11,550,000. |
| RP Seth Maness received a 1-year contract through arbitration worth a total of $1,000,000. |
| LF Oswaldo Arcia received a 1-year contract through arbitration worth a total of $6,875,000. |
| C Nick Hundley was not offered arbitration, becomes a free agent. |
| SP Chris Sale received a 1-year contract through arbitration worth a total of $6,500,000. |
| 3B Asdrubal Cabrera received a 1-year contract through arbitration worth a total of $2,400,000. |
| SP Shelby Miller received a 1-year contract through arbitration worth a total of $1,800,000. |
| Wednesday, November 6th, 2019 |
|---|
| Signed LF Corey D. Ray to a 4-year contract extension worth a total of $34,800,000. |
| Saturday, November 2nd, 2019 |
|---|
| Activated SP Vincent Velasquez from the 60-day disabled list. |
| Activated SP Jon Lester from the 60-day disabled list. |
| Activated RF Josh Reddick from the disabled list. |
| Activated LF Oswaldo Arcia from the disabled list. |
| Activated C Travis d'Arnaud from the disabled list. |
| Recalled 3B Yosvani Bell from Triple A Bridgeport. |
| Recalled CF Akil Baddoo from Triple A Bridgeport. |
| Recalled SS John Devine from Triple A Bridgeport. |
| Recalled SP Buddy Baumann from Triple A Bridgeport. |
| Recalled SP Chris Bassitt from Triple A Bridgeport. |
| Recalled SP Mike Leake from Triple A Bridgeport. |
| Recalled C Nick Hundley from Triple A Bridgeport. |
| Recalled LF Ryan Rua from Triple A Bridgeport. |
| Friday, November 1st, 2019 |
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| RP Tony Watson declines his contract option. |
| RP Chris Archer declines his contract option. |
| Pitching Coach Carlos Carrion leaves the team, his contract was not renewed. |
| Scouting Director Thomas Wayne leaves the team, his contract was not renewed. |
| Sunday, August 25th, 2019 |
|---|
| Placed C Travis d'Arnaud on the 15-day disabled list, retroactive to 08/10/2019. |
| Placed LF Oswaldo Arcia on the 15-day disabled list, retroactive to 07/27/2019. |
| Placed C Salvador Perez on the active roster. |
| Activated C Salvador Perez from the disabled list. |
| Placed SP Gio Gonzalez on the active roster. |
| Activated SP Gio Gonzalez from the 60-day disabled list. |
| Placed RF Josh Reddick on the 15-day disabled list, retroactive to 07/07/2019. |
| Placed CF Adam Jones on the active roster. |
| Activated CF Adam Jones from the disabled list. |
| Demoted SP Mike Leake to Triple A Bridgeport. |
| Placed 3B Matt E. Duffy on the active roster. |
| Activated 3B Matt E. Duffy from the disabled list. |
| Saturday, July 13th, 2019 |
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| Demoted LF Chris Lewandowski to Short Season A Connecticut. |
| Monday, July 8th, 2019 |
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| Demoted 2B Jalen Hunt to Short Season A Connecticut. |
| Friday, July 5th, 2019 |
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| Failed to sign 2nd round draft pick Chris McCluskey. |
| Failed to sign 3rd round draft pick Matt Boguta. |
| Failed to sign 5th round draft pick Matt Rhodes. |
| Friday, June 28th, 2019 |
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| Signed Chris Lewandowski to a minor league contract with a signing bonus of $1,220,000. |
| Sunday, June 23rd, 2019 |
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| Signed Jalen Hunt to a minor league contract with a signing bonus of $180,000. |
| Thursday, June 20th, 2019 |
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| Placed SP Jon Lester on the 60-day disabled list. |
| Purchased the contract of SP Mike Leake from Triple A Bridgeport. |
| Tuesday, May 28th, 2019 |
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| Placed C Salvador Perez on the 15-day disabled list, retroactive to 05/21/2019. |
| Purchased the contract of C Gavin Stupienski from Triple A Bridgeport. |
| Tuesday, April 23rd, 2019 |
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| RF Jonathan Roof was designated for assignment and placed on waivers. |
| Thursday, April 18th, 2019 |
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| Demoted SP Chris Archer to Triple A Bridgeport. |
| Demoted CF Delino DeShields Jr. to Triple A Bridgeport. |
| Wednesday, April 3rd, 2019 |
|---|
| Sent CF Akil Baddoo from spring training camp to Triple A Bridgeport. |
| Sent RF Jonathan Roof from spring training camp to Triple A Bridgeport. |
| Sent RF Corey Dickerson from spring training camp to Triple A Bridgeport. |
| Sent SP Buddy Baumann from spring training camp to Triple A Bridgeport. |
| Sent SP Chris Bassitt from spring training camp to Triple A Bridgeport. |
| Sent C Gavin Stupienski from spring training camp to Triple A Bridgeport. |
| Sent C Nick Hundley from spring training camp to Triple A Bridgeport. |
| Sent 3B Yosvani Bell from spring training camp to Triple A Bridgeport. |
| Sent SS John Devine from spring training camp to Triple A Bridgeport. |
| Sent LF Ryan Rua from spring training camp to Triple A Bridgeport. |
| Placed 3B Matt E. Duffy on the 15-day disabled list, retroactive to 03/31/2019. |
| Placed CF Adam Jones on the 15-day disabled list, retroactive to 03/28/2019. |
| Placed LF Oswaldo Arcia on the active roster. |
| Activated LF Oswaldo Arcia from the 60-day disabled list. |
| Sent SP Mike Leake from spring training camp to Triple A Bridgeport. |
| SP Chris Archer was designated for assignment and placed on waivers. |
| CF Delino DeShields Jr. was designated for assignment and placed on waivers. |
| Thursday, February 28th, 2019 |
|---|
| Purchased the contract of RF Corey Dickerson from Triple A Bridgeport. |
| Purchased the contract of RF Jonathan Roof from Triple A Bridgeport. |
| Purchased the contract of CF Akil Baddoo from Triple A Bridgeport. |
| Purchased the contract of SP Chris Bassitt from Triple A Bridgeport. |
