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| Monday, October 29th , 2001 |
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| LF John Titus retired from professional baseball. |
| Signed Pitching Coach Kevin Tibke to a 3-year contract extension. |
| Monday, September 17th , 2001 |
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| Placed SP Kerry Wood on the 10-day injured list, retroactive to 09/14/2001. |
| Purchased the contract of SP Claude Osteen from Triple A Columbus. |
| Assigned RP Mike Ignasiak to Triple A Columbus. |
| Thursday, September 13th , 2001 |
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| Assigned 1B Tip O'Neill to Double A Albuquerque. |
| Assigned SP Claude Osteen to Triple A Columbus. |
| Optioned SP Frank Sullivan to Triple A Columbus. |
| Purchased the contract of SP Jim Clinton from Triple A Columbus. |
| Monday, September 10th , 2001 |
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| Sent SP Jim Clinton to Triple A Columbus for injury rehab. |
| 1B Tip O'Neill was designated for assignment and placed on waivers. |
| SP Claude Osteen was designated for assignment and placed on waivers. |
| Saturday, September 8th , 2001 |
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| Signed free agent RP Jack Killilay to a 2-year contract worth a total of $6,800,000. |
| Monday, September 3rd , 2001 |
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| Placed LF Pete Browning on the 10-day injured list. |
| Purchased the contract of 3B Dave Malarcher from Triple A Columbus. |
| Monday, August 27th , 2001 |
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| Assigned RP Bruce Sutter to Triple A Columbus. |
| Thursday, August 23rd , 2001 |
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| Assigned RP Ed Fallenstein to Class A Bingo Long's. |
| Purchased the contract of LF Pete Browning from Triple A Columbus. |
| Transferred SP John Flynn to the 60-day IL. |
| RP Bruce Sutter was designated for assignment and placed on waivers. |
| Purchased the contract of SP Scott Downs from Triple A Columbus. |
| Purchased the contract of SP Frank Sullivan from Triple A Columbus. |
| Purchased the contract of SP Kerry Wood from Double A Albuquerque. |
| Purchased the contract of RF Tony Conigliaro from Triple A Columbus. |
| Purchased the contract of LF Billy L Williams from Triple A Columbus. |
| Purchased the contract of 2B Billy Herman from Triple A Columbus. |
| Monday, August 20th , 2001 |
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| Sent LF Pete Browning to Triple A Columbus for injury rehab. |
| Saturday, August 18th , 2001 |
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| Assigned RF Dan Ford to Triple A Columbus. |
| Friday, August 17th , 2001 |
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| RF Dan Ford was designated for assignment and placed on waivers. |
| Thursday, August 16th , 2001 |
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| Optioned 2B Billy Herman to Triple A Columbus. |
| Purchased the contract of 2B Ryne Sandberg from Triple A Columbus. |
| Wednesday, August 15th , 2001 |
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| Placed SP Jim Clinton on the 10-day injured list. |
| Purchased the contract of SP Bob Shaw from Triple A Columbus. |
| Monday, August 13th , 2001 |
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| Sent 2B Ryne Sandberg to Triple A Columbus for injury rehab. |
| Wednesday, August 8th , 2001 |
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| Signed SP Eddie Rommel to a 4-year contract extension worth a total of $1,100,000. |
| Placed LF Pete Browning on the 10-day injured list. |
| Purchased the contract of RF John Titus from Triple A Columbus. |
| Monday, August 6th , 2001 |
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| Optioned SP Bob Shaw to Triple A Columbus. |
| Purchased the contract of 1B Anthony Rizzo from Triple A Columbus. |
| Optioned 1B Cap Anson to Triple A Columbus. |
| Purchased the contract of SP Jim Clinton from Triple A Columbus. |
| Sunday, August 5th , 2001 |
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| Signed 1B Tip O'Neill to a 3-year contract extension worth a total of $6,520,000. |
| Signed RP Hector Neris to a 3-year contract extension worth a total of $1,130,000. |
| Thursday, August 2nd , 2001 |
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| Sent 1B Anthony Rizzo to Triple A Columbus for injury rehab. |
| Wednesday, August 1st , 2001 |
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| Placed 2B Ryne Sandberg on the 10-day injured list. |
| Purchased the contract of 2B Billy Herman from Triple A Columbus. |
| Monday, July 30th , 2001 |
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| Assigned 1B Tip O'Neill to Class A Bingo Long's. |
| Thursday, July 26th , 2001 |
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| Sent SP Jim Clinton to Triple A Columbus for injury rehab. |
| Assigned RP Hector Neris to Class A Bingo Long's. |
| Tuesday, July 24th , 2001 |
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| Signed free agent 1B Tip O'Neill to a 1-year contract worth a total of $2,760,000. |
| Thursday, July 19th , 2001 |
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| Assigned RP John Romonosky to Class A Bingo Long's. |
| Assigned RP Randy Moffitt to Triple A Columbus. |
| Monday, July 16th , 2001 |
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| Assigned SP Wade Miller to Double A Albuquerque. |
| Assigned RP Chris Mahoney to Class A Bingo Long's. |
| Tuesday, July 10th , 2001 |
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| Traded 21-year old 2B Frank Grant to the San Francisco Sea Lions, getting 19-year old minor league 1B John Beckwith and a 3rd round draft pick in return. |
| Traded 23-year old minor league SS Luis Aparicio, 29-year old 3B Jung Ho Kang, and a 7th round draft pick to the Philadelphia Stars, getting 32-year old RHP Larry Jackson in return. |
| Traded 36-year old 1B Joe Harris and 34-year old RHP Lee Smith to the Kansas City Monarchs, getting 19-year old minor league CF Heliodoro Hidalgo, 29-year old minor league LHP Jimmy Key, and a 3rd round draft pick in return. |
| Assigned 3B John Beckwith to Triple A Columbus. |
| Placed RP Larry Jackson on the active roster. |
| Placed SP Jimmy Key on the active roster. |
| Optioned CL Bruce Sutter to Triple A Columbus. |
| Purchased the contract of 1B Mark McGwire from Triple A Columbus. |
| Purchased the contract of 1B Cap Anson from Double A Albuquerque. |
| Purchased the contract of SS Craig Reynolds from Double A Albuquerque. |
| Assigned RP Tom Tuckey to Double A Albuquerque. |
| Monday, July 2nd , 2001 |
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| Placed 1B Anthony Rizzo on the 10-day injured list, retroactive to 06/29/2001. |
| Purchased the contract of 3B Jung Ho Kang from Triple A Columbus. |
| Saturday, June 23rd , 2001 |
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| Signed free agent RP Rube Vickers to a 1-year contract worth a total of $1,900,000. |
| Saturday, June 16th , 2001 |
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| Optioned RP Frank Sullivan to Triple A Columbus. |
| Purchased the contract of SP Karl Spooner from Triple A Columbus. |
| Placed SP Jim Clinton on the 10-day injured list. |
| Purchased the contract of SP Bob Shaw from Triple A Columbus. |
| Monday, June 11th , 2001 |
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| Optioned RP Wade Miley to Triple A Columbus. |
| Optioned RP Kerry Wood to Triple A Columbus. |
| Purchased the contract of SP Kyle Peterson from Triple A Columbus. |
| Purchased the contract of SP Jim Clinton from Triple A Columbus. |
| Thursday, June 7th , 2001 |
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| Assigned RP Vinnie Pestano to Class A Bingo Long's. |
| Monday, June 4th , 2001 |
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| Assigned RP Don Elston to Class A Bingo Long's. |
| Thursday, May 31st , 2001 |
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| Assigned RP Pat House to Double A Albuquerque. |
| Assigned RP Rob Scahill to Class A Bingo Long's. |
| Saturday, May 26th , 2001 |
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| Signed free agent RP Bill Landrum to a 1-year contract worth a total of $2,920,000. |
| Thursday, May 24th , 2001 |
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| Assigned 2B Orlando Cabrera to Triple A Columbus. |
| Monday, May 21st , 2001 |
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| Optioned 1B Bob Robertson to Triple A Columbus. |
| Placed LF Pete Browning on the active roster. |
| Activated LF Pete Browning from the injured list. |
| 2B Orlando Cabrera was designated for assignment and placed on waivers. |
| Friday, May 18th , 2001 |
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| Signed free agent SP Vito Tamulis to a 1-year contract worth a total of $8,500,000. |
| Assigned CL Ad Gumbert to Class A Bingo Long's. |
| Monday, May 7th , 2001 |
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| Assigned RF John Titus to Triple A Columbus. |
| Optioned 2B Orlando Cabrera to Triple A Columbus. |
| Purchased the contract of 2B Frank Grant from Triple A Columbus. |
| Monday, April 30th , 2001 |
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| Sent 2B Frank Grant to Triple A Columbus for injury rehab. |
| Monday, April 16th , 2001 |
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| Signed free agent RP Bob Geary to a 1-year contract worth a total of $7,100,000. |
| Sent RP Ad Gumbert to Triple A Columbus for injury rehab. |
| Saturday, April 14th , 2001 |
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| Placed LF Pete Browning on the 10-day injured list, retroactive to 04/13/2001. |
| Purchased the contract of 1B Bob Robertson from Triple A Columbus. |
| Monday, April 9th , 2001 |
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| Signed free agent RP Stan Yerkes to a 1-year contract worth a total of $2,160,000. |
| Thursday, April 5th , 2001 |
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| Optioned SP Kyle Peterson to Triple A Columbus. |
| Placed CL Bruce Sutter on the active roster. |
| Activated CL Bruce Sutter from the injured list. |
| Tuesday, April 3rd , 2001 |
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| Placed RP Ad Gumbert on the 10-day injured list. |
| Purchased the contract of SP Kyle Peterson from Triple A Columbus. |
| Monday, April 2nd , 2001 |
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| Assigned SP Rufe Gentry to Class A Bingo Long's. |
| Assigned SP Ad Brennan to Class A Bingo Long's. |
| Wednesday, March 28th , 2001 |
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| Assigned SP Scott Downs from Spring Training camp to Triple A Columbus. |
| Assigned SP Kyle Peterson from Spring Training camp to Triple A Columbus. |
| Optioned 1B Cap Anson to Triple A Columbus. |
| Assigned 1B Bob Robertson from Spring Training camp to Triple A Columbus. |
| Assigned RP Arnold Carter from Spring Training camp to Triple A Columbus. |
| Tuesday, March 27th , 2001 |
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| Assigned LF Cy Williams from Spring Training camp to Triple A Columbus. |
| Placed CL Bruce Sutter on the 10-day injured list, retroactive to 03/24/2001. |
| Optioned RF Dan Ford to Triple A Columbus. |
| Monday, March 26th , 2001 |
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| Optioned SP Jocko Flynn to Triple A Columbus. |
| Sunday, March 25th , 2001 |
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| Optioned SP Claude Osteen to Triple A Columbus. |
| Saturday, March 24th , 2001 |
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| Assigned RP Bill Shores to Class A Bingo Long's. |
| Assigned SS Luis Aparicio from Spring Training camp to Triple A Columbus. |
| Friday, March 23rd , 2001 |
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| Optioned RP Tom Niedenfuer to Triple A Columbus. |
| Wednesday, March 21st , 2001 |
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| Assigned RP Chad Kuhl from Spring Training camp to Triple A Columbus. |
| Assigned C Eugene Hargrave from Spring Training camp to Triple A Columbus. |
| Placed 2B Frank Grant on the 10-day injured list, retroactive to 03/18/2001. |
| Assigned 3B Chris Brown from Spring Training camp to Triple A Columbus. |
| Assigned 3B Deacon White from Spring Training camp to Triple A Columbus. |
| Assigned 2B Bunny Downs from Spring Training camp to Triple A Columbus. |
| Assigned CF Jerry Mumphrey from Spring Training camp to Triple A Columbus. |
| LF Luis Gonzalez was designated for assignment and placed on waivers. |
| Traded 24-year old 2B Charlie Gehringer and a 3rd round draft pick to the Detroit Wolverines, getting 23-year old minor league LHP Claude Osteen and a 1st round draft pick in return. |
| Placed SP Claude Osteen on the active roster. |
| Traded 29-year old C Gabby Hartnett, 23-year old minor league RHP Rollie Fingers, and a 4th round draft pick to the Memphis Red Sox, getting 25-year old RF Sammy Sosa in return. |
| Placed RF Sammy Sosa on the active roster. |
| Thursday, March 15th , 2001 |
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| Assigned 1B Mark Grace to Triple A Columbus. |
| Wednesday, March 14th , 2001 |
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| 1B Mark Grace was designated for assignment and placed on waivers. |
| Friday, March 9th , 2001 |
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| Assigned 1B Mark McGwire to Class A Bingo Long's. |
| Thursday, March 8th , 2001 |
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| Assigned RP Bill Stoneman from Spring Training camp to Class A Bingo Long's. |
| Assigned SP Jim Clinton from Spring Training camp to Class A Bingo Long's. |
| Assigned SP Larry Dierker from Spring Training camp to Class A Bingo Long's. |
| Assigned RP Karl Spooner from Spring Training camp to Class A Bingo Long's. |
| Assigned RP Ken McBride from Spring Training camp to Class A Bingo Long's. |
| Assigned C Darren Daulton from Spring Training camp to Class A Bingo Long's. |
| Assigned 1B Cody Bellinger from Spring Training camp to Class A Bingo Long's. |
| 1B Mark McGwire was designated for assignment and placed on waivers. |
| Assigned 3B Jung Ho Kang from Spring Training camp to Class A Bingo Long's. |
| Assigned 2B Billy Herman from Spring Training camp to Class A Bingo Long's. |
| Assigned SS Craig Reynolds from Spring Training camp to Class A Bingo Long's. |
| Assigned LF Billy L Williams from Spring Training camp to Class A Bingo Long's. |
| Assigned RF Fred Lynn from Spring Training camp to Class A Bingo Long's. |
| Assigned RF Tony Conigliaro from Spring Training camp to Class A Bingo Long's. |
| Monday, February 26th , 2001 |
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| Invited non-roster SP Fergie Jenkins to Spring Training camp. |
| Invited non-roster SP Rick Reuschel to Spring Training camp. |
| Invited non-roster SP CC Sabathia to Spring Training camp. |
| Invited non-roster RP Frank Sullivan to Spring Training camp. |
| Invited non-roster RP Wade Miley to Spring Training camp. |
| Invited non-roster RP Lee Smith to Spring Training camp. |
| Invited non-roster RP Kerry Wood to Spring Training camp. |
| Invited non-roster C Frank Chance to Spring Training camp. |
| Invited non-roster 2B Frank Grant to Spring Training camp. |
| Invited non-roster SP Scott Downs to Spring Training camp. |
| Invited non-roster RP Tom Niedenfuer to Spring Training camp. |
| Invited non-roster 2B Bunny Downs to Spring Training camp. |
| Invited non-roster 1B Cody Bellinger to Spring Training camp. |
| Invited non-roster RP Ad Gumbert to Spring Training camp. |
| Invited non-roster SS Luis Aparicio to Spring Training camp. |
| Invited non-roster RP Karl Spooner to Spring Training camp. |
| Invited non-roster 1B Mark Grace to Spring Training camp. |
| Invited non-roster RF Tony Conigliaro to Spring Training camp. |
| Invited non-roster 3B Cap Anson to Spring Training camp. |
| Invited non-roster C Darren Daulton to Spring Training camp. |
| Invited non-roster LF Billy L Williams to Spring Training camp. |
| Invited non-roster SP Jocko Flynn to Spring Training camp. |
| Invited non-roster 3B Deacon White to Spring Training camp. |
| Invited non-roster RP Bill Stoneman to Spring Training camp. |
| Invited non-roster SS Craig Reynolds to Spring Training camp. |
| Invited non-roster SP Kyle Peterson to Spring Training camp. |
| Invited non-roster CF Jerry Mumphrey to Spring Training camp. |
| Invited non-roster 1B Mark McGwire to Spring Training camp. |
| Invited non-roster RP Ken McBride to Spring Training camp. |
| Invited non-roster 3B Jung Ho Kang to Spring Training camp. |
| Invited non-roster 2B Billy Herman to Spring Training camp. |
| Invited non-roster C Gabby Hartnett to Spring Training camp. |
| Invited non-roster C Bubbles Hargrave to Spring Training camp. |
| Invited non-roster RP Arnold Carter to Spring Training camp. |
| Invited non-roster SS Orlando Cabrera to Spring Training camp. |
| Invited non-roster 2B Charlie Gehringer to Spring Training camp. |
| Invited non-roster RP Chad Kuhl to Spring Training camp. |
| Invited non-roster CF Cy Williams to Spring Training camp. |
| Invited non-roster SP Larry Dierker to Spring Training camp. |
| Invited non-roster 3B Chris Brown to Spring Training camp. |
| Invited non-roster CF Fred Lynn to Spring Training camp. |
| Invited non-roster SP Johnny Podres to Spring Training camp. |
| Invited non-roster 1B Bob Robertson to Spring Training camp. |
| Assigned SP Jim Clinton to Triple A Columbus. |
| Assigned SP Johnny Podres from Spring Training camp to Triple A Columbus. |
| Invited non-roster SP Jim Clinton to Spring Training camp. |
| Thursday, February 22nd , 2001 |
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| SP Jim Clinton was designated for assignment and placed on waivers. |
| Monday, February 19th , 2001 |
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| Assigned SP Kyle Peterson to Class A Bingo Long's. |
| Monday, February 12th , 2001 |
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| Assigned RP Chris Leroux to Class A Bingo Long's. |
| Monday, February 5th , 2001 |
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| Assigned SP Bill Stoneman to Class A Bingo Long's. |
| Monday, January 29th , 2001 |
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| Signed free agent RP Stan Yerkes to a 3-year contract worth a total of $4,680,000. |
| Friday, January 19th , 2001 |
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| Assigned SP Jocko Flynn to Triple A Columbus. |
| Assigned C Bubbles Hargrave to Triple A Columbus. |
| Assigned 1B Trey Mancini to Triple A Columbus. |
| Thursday, January 18th , 2001 |
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| SP Jocko Flynn was designated for assignment and placed on waivers. |
| C Bubbles Hargrave was designated for assignment and placed on waivers. |
| 1B Trey Mancini was designated for assignment and placed on waivers. |
| Monday, January 15th , 2001 |
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| Assigned SP Frank Dwyer to Double A Albuquerque. |
| Assigned SP Bill Lee to Double A Albuquerque. |
| Assigned 1B Cody Bellinger to Double A Albuquerque. |
| Sunday, January 14th , 2001 |
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| Failed to sign 1st round draft pick Zack Greinke. |
| Friday, January 12th , 2001 |
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| Signed Frank Dwyer to a minor league contract with a signing bonus of $95,000. |
| Wednesday, January 10th , 2001 |
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| Signed Cody Bellinger to a minor league contract with a signing bonus of $240,000. |
| Tuesday, January 9th , 2001 |
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| Signed free agent RP Phil Reccius to a 3-year contract worth a total of $7,200,000. |
| Signed Bill Lee to a minor league contract with a signing bonus of $275,000. |
| Monday, January 1st , 2001 |
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| Assigned RP Ad Gumbert to Double A Albuquerque. |
| Assigned C Darren Daulton to Class A Bingo Long's. |
