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| Thursday, November 23rd , 2000 |
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| SP Charlie Wagner received a 1-year contract through automatic renewal worth a total of $555,000. |
| C Hal Wagner becomes a free-agent. |
| SS Tommy Brown becomes a free-agent. |
| SP Ray Herbert becomes a free-agent. |
| CF Adam Jones becomes a free-agent. |
| LF Sixto Lezcano becomes a free-agent. |
| SP Jason Hammel becomes a free-agent. |
| SP Roy Oswalt becomes a free-agent. |
| 2B Marcus Giles becomes a free-agent. |
| RP Tim Belcher becomes a free-agent. |
| RP Kodi Whitley becomes a free-agent. |
| RF Tommy Medica becomes a free-agent. |
| CF Don Young becomes a free-agent. |
| CL Red Witt becomes a free-agent. |
| LF Harlin Pool received a 1-year contract through automatic renewal worth a total of $555,000. |
| 2B Lou Stringer received a 1-year contract through automatic renewal worth a total of $555,000. |
| Tuesday, November 21st , 2000 |
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| RP Mike Dunn received a 1-year contract through arbitration worth a total of $1,217,670. |
| RF Skip Schumaker received a 1-year contract through arbitration worth a total of $1,700,000. |
| C Harry Chiti received a 1-year contract through arbitration worth a total of $1,100,000. |
| RP Fred Baczewski received a 1-year contract through arbitration worth a total of $1,000,000. |
| LF Greg Dobbs received a 1-year contract through arbitration worth a total of $1,100,000. |
| RP Paul Fry received a 1-year contract through arbitration worth a total of $1,584,000. |
| 1B Mike Shannon received a 1-year contract through arbitration worth a total of $2,600,000. |
| RP MacKenzie Gore received a 1-year contract through arbitration worth a total of $1,530,200. |
| RP Johan Oviedo received a 1-year contract through arbitration worth a total of $1,600,000. |
| SP Brad Halsey received a 1-year contract through arbitration worth a total of $3,273,600. |
| RP Dave Beard received a 1-year contract through arbitration worth a total of $1,317,600. |
| Wednesday, October 11th , 2000 |
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| Released SP Tom Gordon. |
| Thursday, September 28th , 2000 |
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| Purchased the contract of RF Tommy Medica from Triple A Chesterfield. |
| Thursday, September 7th , 2000 |
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| Purchased the contract of SP Charlie Wagner from Triple A Chesterfield. |
| Purchased the contract of C Harry Chiti from Triple A Chesterfield. |
| Purchased the contract of SP Fred Baczewski from Triple A Chesterfield. |
| Purchased the contract of RP Paul Fry from Triple A Chesterfield. |
| Tuesday, August 1st , 2000 |
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| Traded 29-year old RHP Mike Fiers to the Milwaukee Brewers, getting 23-year old minor league RHP Bob Osborn and a 3rd round draft pick in return. |
| Purchased the contract of SP Johan Oviedo from Triple A Chesterfield. |
| Sunday, June 25th , 2000 |
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| Signed free agent RF Sixto Lezcano to a 1-year contract worth a total of $5,500,000. |
| Demoted C Harry Chiti to Triple A Chesterfield. |
| Thursday, June 22nd , 2000 |
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| Demoted RP Paul Fry to Triple A Chesterfield. |
| Demoted 1B Joe Hauser to Triple A Chesterfield. |
| Purchased the contract of 3B Greg Dobbs from Triple A Chesterfield. |
| Traded 26-year old minor league 1B Joe Hauser and 29-year old RHP Luke Weaver to the San Francisco Giants, getting 26-year old RHP Tom Gordon, 37-year old RHP Kodi Whitley, a 1st round draft pick, and $1 in cash in return. |
| Traded 25-year old minor league RHP Dave Coggin, 29-year old minor league RHP Clyde King, 28-year old LHP Max Macon, and 29-year old 2B Angel Berroa to the Seattle Mariners, getting 30-year old RHP Aaron Small, 34-year old 2B Jeff Kent, 39-year old RHP Red Witt, a 2nd round draft pick, a 3rd round draft pick, and a 4th round draft pick in return. |
| Thursday, June 1st , 2000 |
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| Demoted CL Greg Bollo to Triple A Chesterfield. |
| Demoted RF Bobby Higginson to Triple A Chesterfield. |
| Purchased the contract of 2B Lou Stringer from Triple A Chesterfield. |
| Purchased the contract of LF Harlin Pool from Triple A Chesterfield. |
| Traded 26-year old minor league RHP Greg Bollo, 26-year old minor league RF Bobby Higginson, and 33-year old 2B Orlando Cabrera to the Milwaukee Brewers, getting 25-year old RHP Dave Coggin, a 1st round draft pick, and a 2nd round draft pick in return. |
| Monday, May 15th , 2000 |
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| Signed free agent SP Roy Oswalt to a 1-year contract worth a total of $7,000,000. |
| Signed free agent 2B Tommy Brown to a 1-year contract worth a total of $13,000,000. |
| Demoted RP Charlie Wagner to Triple A Chesterfield. |
| Demoted 2B Lou Stringer to Triple A Chesterfield. |
| Sunday, May 14th , 2000 |
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| Demoted 3B Greg Dobbs to Triple A Chesterfield. |
| Saturday, May 13th , 2000 |
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| Signed free agent 2B Marcus Giles to a 1-year contract worth a total of $8,500,000. |
| Sunday, April 2nd , 2000 |
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| Demoted RP MacKenzie Gore to Triple A Chesterfield. |
| Demoted RP Johan Oviedo to Triple A Chesterfield. |
| Demoted RP Fred Baczewski to Triple A Chesterfield. |
| Demoted C Harry Chiti to Triple A Chesterfield. |
| Demoted CF Enrique Hernández to Triple A Chesterfield. |
| Demoted 2B Don Buddin to Triple A Chesterfield. |
| Purchased the contract of C Harry Chiti from Triple A Chesterfield. |
| Demoted LF Harlin Pool to Triple A Chesterfield. |
| Purchased the contract of CF Adam Jones from Triple A Chesterfield. |
| Wednesday, March 1st , 2000 |
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| Signed free agent SP Tim Belcher to a 1-year contract worth a total of $1,700,000. |
| Signed free agent SS Orlando Cabrera to a 1-year contract worth a total of $1,600,000. |
| Signed free agent SP Jason Hammel to a 1-year contract worth a total of $1,500,000. |
| Signed free agent SP Ray Herbert to a 1-year contract worth a total of $1,300,000. |
| Tuesday, February 29th , 2000 |
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| Signed free agent C Hal Wagner to a 1-year contract worth a total of $4,000,000. |
| Friday, January 14th , 2000 |
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| Released C Ron Hassey. |
