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| Sunday, February 23rd, 2020 |
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| Signed scouting director Tim Hoeksema. |
| Signed team doctor Steve Finch. |
| Friday, February 21st, 2020 |
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| Signed bench coach Ben Brennecke. |
| Thursday, February 20th, 2020 |
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| Promoted SS Jonathan Masche to Triple A Pawtucket. |
| Promoted CF Alex Schindler to Triple A Pawtucket. |
| Promoted 1B Manny Fauria to Triple A Pawtucket. |
| Promoted LF Wu-han Chia to Triple A Pawtucket. |
| Promoted C Ben Bradley to Double A Portland. |
| Promoted C Jayden Ballard to Double A Portland. |
| Promoted RF Hector Carrillo to Double A Portland. |
| Promoted 2B Luis Sanchez to Double A Portland. |
| Promoted RF Joe McMann to Double A Portland. |
| Promoted SS Mike Swain to Double A Portland. |
| Promoted LF Jaden Chappell to Double A Portland. |
| Promoted LF Josh Rowan to Double A Portland. |
| Sent SP Nick Rios to High-A Salem. |
| Sent SP Steve Wagner to High-A Salem. |
| Sent RP Joe Friese to High-A Salem. |
| Sent SP Andres Gutierrez to High-A Salem. |
| Sent RP Mike Ward to High-A Salem. |
| Sent RP Gerben Dikken to High-A Salem. |
| Sent 3B Rod Neira to High-A Salem. |
| Received SP Mike Eddy from Low-A Lowell. |
| Received SP Victor Munoz from Low-A Lowell. |
| Received SP Dan Chambers from Low-A Lowell. |
| Received RP Steve Randolph from Low-A Lowell. |
| Received CL David Quintero from Low-A Lowell. |
| Received SP Pat Alt from Low-A Lowell. |
| Received C Dave Shoemaker from Rookie League Fort Myers (BOS). |
| Received C Nelson Gardea from Rookie League Fort Myers (BOS). |
| Received 2B Marco Castillo from Rookie League Fort Myers (BOS). |
| Received LF Kevin Block from Rookie League Fort Myers (BOS). |
| Received SS Bob Lopez from Rookie League Fort Myers (BOS). |
| Received 2B Alex Quinones from Rookie League Fort Myers (BOS). |
| Received LF Franklin Sanchez from Rookie League Fort Myers (BOS). |
| Received CF Mike Davis from Rookie League Fort Myers (BOS). |
| Received LF Jose Buonaiuti from Rookie League Fort Myers (BOS). |
| Received 1B Alex Pena from Rookie League Fort Myers (BOS). |
| Received 3B Mike Hanson from Rookie League Fort Myers (BOS). |
| Received RF Tony McMillian from Rookie League Fort Myers (BOS). |
| Received RF Wilfredo Sanchez from Rookie League Fort Myers (BOS). |
| Sent 3B Kevin Block to High-A Salem. |
| Sent 2B Alex Quinones to High-A Salem. |
| Sent LF Franklin Sanchez to High-A Salem. |
| Received RP Mike Ward from High-A Salem. |
| Received RP Gerben Dikken from High-A Salem. |
| Received C David Gonzales from High-A Salem. |
| Received SS Tony Rodriquez from Low-A Lowell. |
| Received RF Salvadaro Sengo from Low-A Lowell. |
| Received 3B Julian Grover from Low-A Lowell. |
| Demoted RP Pat Alt to Low-A Lowell. |
| Demoted RP David Quintero to Low-A Lowell. |
| Demoted C Nelson Gardea to Low-A Lowell. |
| Received SP Stephen Keller from Triple A Pawtucket. |
| Received 1B Kevin Block from High-A Salem. |
| Demoted SP Dan Chambers to Low-A Lowell. |
| Demoted 3B Julian Grover to Low-A Lowell. |
| Sent 3B Kevin Block to High-A Salem. |
| Received 2B Dave Todd from Low-A Lowell. |
| Received LF Franklin Sanchez from High-A Salem. |
| Demoted LF Salvadaro Sengo to Low-A Lowell. |
