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| Thursday, March 5th , 2099 |
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| Promoted international complex member SP Arturo Rivera to Rookie League Toronto (GCL). |
| Promoted international complex member SP Mario Santiago to Rookie League Toronto (GCL). |
| Promoted international complex member RF Jose Renteria to Rookie League Toronto (GCL). |
| Purchased the contract of 1B Kevin Winter from Double A New Hampshire. |
| Purchased the contract of SS Brian Burton from Double A New Hampshire. |
| Purchased the contract of RP Harry Reid from High-A Dunedin. |
| Purchased the contract of SP Jonathan McBride from Triple A Buffalo. |
| Purchased the contract of SS Damani Fowlkes from Triple A Buffalo. |
| Purchased the contract of 2B Greg Phillips from Triple A Buffalo. |
| Purchased the contract of C William Taveras from Triple A Buffalo. |
| Purchased the contract of CF Steve Bova from Class A Lansing. |
| Purchased the contract of SP Gary Brooks from Triple A Buffalo. |
| Placed CF Greg Bates on the active roster. |
| Tuesday, February 10th , 2099 |
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| Signed free agent CF Mario Rosario to a minor league contract with a $20,000 signing bonus. |
| Signed international amateur SS Alex Duran out of Venezuela to a minor league contract with a $310,000 signing bonus. |
| Signed international amateur LF Eduardo Rutz out of Dominican Republic to a minor league contract with a $360,000 signing bonus. |
| Signed international amateur SP Mike Solis out of Dominican Republic to a minor league contract with a $430,000 signing bonus. |
| Traded 31-year old SS Brian Jones (retaining 40%), 28-year old LHP Domingo Tamayo, 23-year old LHP Curtis Moore, and 22-year old minor league RHP Josh Montgomery to the Chicago White Sox, getting 24-year old CF Greg Bates and a 6th round draft pick in return. |
| Placed RP Curt Tupper on the active roster. |
| Assigned C Kenny Franks to Triple A Buffalo. |
| Monday, January 19th , 2099 |
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| Signed free agent SP Curt Tupper to a 3-year contract worth a total of $11,500,000. |
| Signed free agent SP Rodolfo Piedra to a minor league contract. |
| Traded $1 in cash and $4,900,000 in international amateur bonus pool room to the Chicago White Sox, getting $1 in cash in return. |
| Traded $1 in cash and $9,000,000 in international amateur bonus pool room to the Chicago Cubs, getting $1 in cash in return. |
| Received former Rule 5 draft pick C Kenny Franks from the Los Angeles Dodgers. |
| Thursday, January 8th , 2099 |
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| Signed 1B Dennis Desper to a 1-year contract extension worth a total of $24,800,000. |
| Promoted RP Jim Rainey from Low-A Vancouver to Class A Lansing. |
| Promoted RP Josh Montgomery from High-A Dunedin to Double A New Hampshire. |
| Sent RP Kevin Brannon from Class A Lansing to High-A Dunedin. |
| Sent SP Nick Bondi from Class A Lansing to High-A Dunedin. |
| Promoted SP Angel Arellano from Low-A Vancouver to High-A Dunedin. |
| Promoted 2B Devon Phillips from Rookie League Toronto (GCL) to Class A Lansing. |
| Promoted 3B Marcos Amor from Rookie League Bluefield to Low-A Vancouver. |
| Sent C Alvaro Chairez from Rookie League Toronto (GCL) to Rookie League Bluefield. |
