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Sunday, December 26th , 1999
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Signed free agent CF Rick Miller to a minor league contract with a major league option.
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Friday, December 24th , 1999
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Signed free agent RP Mike Stanton to a 1-year contract worth a total of $1,750,000.
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Monday, December 6th , 1999
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Signed SS Matt Williams to a 6-year contract extension worth a total of $42,000,000.
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Monday, November 29th , 1999
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Signed SP Tommy Milone to a 6-year contract extension worth a total of $22,500,000.
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Signed SP Kirk Rueter to a 6-year contract extension worth a total of $30,000,000.
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Thursday, November 25th , 1999
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SP Jose Rijo becomes a free-agent.
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1B Tony Lupien received a 1-year contract through automatic renewal worth a total of $555,000.
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SS Matt Williams received a 1-year contract through automatic renewal worth a total of $555,000.
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RP Wally Ritchie becomes a free-agent.
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SP Sammy Ellis received a 1-year contract through automatic renewal worth a total of $555,000.
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C Keibert Ruiz received a 1-year contract through automatic renewal worth a total of $555,000.
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SP Kirk Rueter received a 1-year contract through automatic renewal worth a total of $555,000.
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1B Mike Carp received a 1-year contract through automatic renewal worth a total of $555,000.
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RP Jovani Moran received a 1-year contract through automatic renewal worth a total of $555,000.
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RP Joey Eischen received a 1-year contract through automatic renewal worth a total of $555,000.
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SP Tommy Milone received a 1-year contract through automatic renewal worth a total of $555,000.
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CF Jim Russell becomes a free-agent.
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RP Severino Gonzalez received a 1-year contract through automatic renewal worth a total of $555,000.
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RP Win Ballou becomes a free-agent.
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RP Rob Rasmussen becomes a free-agent.
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SP Harry Feldman becomes a free-agent.
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Tuesday, November 23rd , 1999
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RP Ted Abernathy received a 1-year contract through arbitration worth a total of $1,163,280.
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RP Blaine Boyer received a 1-year contract through arbitration worth a total of $850,000.
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SS Wilmer Difo was not offered arbitration, becomes a free agent.
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RP Robinson Tejeda was not offered arbitration, becomes a free agent.
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Sunday, November 7th , 1999
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Signed RF Debs Garms to a 2-year contract extension worth a total of $1,300,000.
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Thursday, October 7th , 1999
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Signed 3B Miguel Andújar to a minor league contract extension.
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Thursday, September 9th , 1999
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Signed free agent RP Rob Rasmussen to a minor league contract.
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Thursday, August 19th , 1999
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Signed free agent RP Win Ballou to a minor league contract with a $60,000 signing bonus.
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Saturday, June 26th , 1999
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Signed DH Jack Rothrock to a 6-year contract extension worth a total of $211,200,000.
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Thursday, June 24th , 1999
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Signed free agent RP Wally Ritchie to a 1-year contract worth a total of $555,000.
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Thursday, June 3rd , 1999
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Signed free agent 3B Miguel Andújar to a minor league contract.
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Signed free agent 3B Dean Palmer to a minor league contract.
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Signed free agent SP Harry Feldman to a minor league contract.
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Signed free agent RP Brian Maxcy to a minor league contract.
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Signed free agent RP Jerry Robertson to a minor league contract.
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Saturday, May 15th , 1999
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Signed SP Sam Jones to a 6-year contract extension worth a total of $34,500,000.
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Sunday, May 2nd , 1999
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RF Kirk Gibson did not elect for free agency and will remain in the Chicago (N) organization.
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Wednesday, January 27th , 1999
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Signed free agent RF Kirk Gibson to a minor league contract with a major league option.
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Tuesday, January 12th , 1999
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Drafted CF Julio Rodriguez in the 1998 first-year player draft (Round 1, Pick 10, 10th overall pick).
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Drafted SP Kirk Rueter in the 1998 first-year player draft (Round 1, Pick 17, 17th overall pick).
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Drafted RP Jovani Moran in the 1998 first-year player draft (Round 2, Pick 8, 28th overall pick).
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Drafted LF Jonny Gomes in the 1998 first-year player draft (Round 2, Pick 10, 30th overall pick).
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Drafted RF Paul Householder in the 1998 first-year player draft (Round 2, Pick 14, 34th overall pick).
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Drafted RP Jesse Orosco in the 1998 first-year player draft (Round 2, Pick 17, 37th overall pick).
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Drafted RP Dustin McGowan in the 1998 first-year player draft (Round 3, Pick 8, 48th overall pick).
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Drafted 2B Fernando Gonzalez in the 1998 first-year player draft (Round 3, Pick 10, 50th overall pick).
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Drafted CF Jose Zardon in the 1998 first-year player draft (Round 3, Pick 17, 57th overall pick).
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Drafted RP George Lauzerique in the 1998 first-year player draft (Round 4, Pick 10, 70th overall pick).
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Drafted RP David McKay in the 1998 first-year player draft (Round 5, Pick 10, 90th overall pick).
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Drafted 2B Edwin Diaz in the 1998 first-year player draft (Round 6, Pick 10, 110th overall pick).
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Thursday, January 7th , 1999
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Signed free agent 3B Willy Aybar to a 2-year contract worth a total of $10,000,000.
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