Sunday, June 22nd, 1969
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Montreal Expos: Signed SS Don Buddin to a 6-year contract extension worth a total of $39,000,000.
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Friday, June 20th, 1969
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Montreal Expos: Signed CF Irv Noren to a 1-year contract extension worth a total of $2,000,000.
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Pittsburgh Pirates: Signed RP Darren Holmes to a 4-year contract extension worth a total of $48,000,000.
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Pittsburgh Pirates: Signed RP Stan Thomas to a 3-year contract extension worth a total of $22,000,000.
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Montreal Expos: Signed SP Denny McLain to a 3-year contract extension worth a total of $31,500,000.
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Pittsburgh Pirates: Signed CF Vada Pinson to a 6-year contract extension worth a total of $102,000,000.
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Friday, April 25th, 1969
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Montreal Expos: Signed RP Cy Buker to a 2-year contract extension worth a total of $10,000,000.
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Thursday, April 10th, 1969
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Bronx Yankees: Signed free agent RP Wilton Lopez to a 1-year contract worth a total of $1,250,000.
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Saturday, February 1st, 1969
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New York Mets: Signed free agent RP Cam Bedrosian to a 1-year contract worth a total of $1,800,000.
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Detroit Tigers: Signed free agent RP Gabe Molina to a minor league contract.
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Milwaukee Brewers: Signed free agent CF Ron E Davis to a minor league contract.
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Milwaukee Brewers: Signed free agent RP Chuck Seelbach to a 2-year contract worth a total of $5,000,000.
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Colorado Rockies: Signed free agent SP Bob Cain to a 2-year contract worth a total of $14,560,000.
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Milwaukee Brewers: Signed free agent 3B Rick Schu to a 3-year contract worth a total of $13,500,000.
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Detroit Tigers: Signed free agent RP Kanekoa Texeira to a minor league contract.
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Milwaukee Brewers: Released SS Ray Morehart.
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Milwaukee Brewers: Released RP Augie Walsh.
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Milwaukee Brewers: Released RP Henry Owens.
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Milwaukee Brewers: Released 3B Terry Pendleton.
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The Chicago Cubs traded 28-year-old catcher Miguel Montero to the Miami Marlins, getting 24-year-old minor league right fielder Jack Voigt in return.
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The Kansas City Royals traded 35-year-old minor league starting pitcher Dick Pole to the Miami Marlins, getting $1 in cash in return.
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Wednesday, January 8th, 1969
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St. Louis Cardinals: Signed free agent CF Paul Blair to a minor league contract.
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Detroit Tigers: Signed free agent SP Toby Borland to a 1-year contract worth a total of $2,800,000.
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Baltimore Orioles: Signed free agent SP Francisco Cordova to a 3-year contract worth a total of $39,000,000.
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St. Louis Cardinals: Signed free agent SP Bill F Henry to a minor league contract.
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Chicago Cubs: Signed SS Ed Romero to a 4-year contract extension worth a total of $7,000,000.
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Detroit Tigers: Signed free agent 3B Floyd Rayford to a minor league contract.
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St. Louis Cardinals: Signed free agent RF Jim Fuller to a minor league contract.
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New York Mets: Signed free agent C Eddie Kenna to a 1-year contract worth a total of $1,100,000.
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