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| Thursday, November 6th, 1969 |
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| SP Vincent Velasquez retires. |
| Monday, October 6th, 1969 |
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| Demoted RP Don Kirkwood to Triple A Albuquerque. |
| Demoted LF Milt Bocek to Triple A Albuquerque. |
| Demoted LF Dick Davis to Triple A Albuquerque. |
| Released CF Howie Goss. |
| Demoted C Eddie Kenna to Triple A Albuquerque. |
| Demoted C Brad Ausmus to Triple A Albuquerque. |
| Demoted RP Tom Davey to Triple A Albuquerque. |
| Demoted SP Clise Dudley to Triple A Albuquerque. |
| Demoted SP Steve Comer to Triple A Albuquerque. |
| Demoted 2B Bobby Mattick to Triple A Albuquerque. |
| Purchased the contract of LF John Stephenson from Triple A Albuquerque. |
| Released RP Cam Bedrosian. |
| Released SP Vincent Velasquez. |
| Purchased the contract of LF Dick Davis from Triple A Albuquerque. |
| Purchased the contract of C Brad Ausmus from Triple A Albuquerque. |
| Demoted RP Severino Gonzalez to Triple A Albuquerque. |
| Purchased the contract of 2B Bobby Mattick from Triple A Albuquerque. |
| Demoted C Brad Ausmus to Triple A Albuquerque. |
| Purchased the contract of C Eddie Kenna from Triple A Albuquerque. |
| Wednesday, October 1st, 1969 |
|---|
| Purchased the contract of SP George Jeffcoat from Triple A Albuquerque. |
| Demoted SP George Jeffcoat to Triple A Albuquerque. |
| Purchased the contract of SP Steve Comer from Triple A Albuquerque. |
| Monday, September 1st, 1969 |
|---|
| Purchased the contract of SP D J Houlton from Triple A Albuquerque. |
| Demoted SP D J Houlton to Triple A Albuquerque. |
| Purchased the contract of RP Don Kirkwood from Triple A Albuquerque. |
| Wednesday, July 16th, 1969 |
|---|
| Traded 35-year-old center fielder Carl Furillo and 26-year-old starting pitcher John Mitchell to the South Side White Sox, getting 29-year-old shortstop Jose Ramirez and 28-year-old reliever Scott Stewart in return. |
| Traded 25-year-old minor league starting pitcher Jose Lima to the Brooklyn Dodgers, getting 31-year-old reliever Jimmie Keenan in return. |
| Tuesday, July 1st, 1969 |
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| Demoted RF Cody Ross to Triple A Albuquerque. |
| Purchased the contract of LF Dick Davis from Triple A Albuquerque. |
| Thursday, June 5th, 1969 |
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| Signed CF Kirby Puckett to a 6-year contract extension worth a total of $196,800,000. |
| Thursday, May 1st, 1969 |
|---|
| Purchased the contract of SP Clise Dudley from Triple A Albuquerque. |
| Demoted SP Clise Dudley to Triple A Albuquerque. |
| Traded 29-year-old minor league right fielder Scott Northey and $1 in cash to the Chicago Cubs, getting 29-year-old left fielder Bob Elliott, 29-year-old minor league reliever Bill Dailey and 30-year-old shortstop Ed Romero in return. |
| Traded 32-year-old minor league shortstop Al Lefevre and 25-year-old left fielder Dwight Evans to the South Side White Sox, getting 31-year-old center fielder Kirby Puckett, 34-year-old left fielder Josh Reddick and 26-year-old starting pitcher John Mitchell in return. |
| Traded 31-year-old starting pitcher Nick Willhite and $1 in cash to the Miami Marlins, getting 35-year-old center fielder Carl Furillo in return. |
| Released LF Josh Reddick. |
| Wednesday, April 16th, 1969 |
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| Demoted CF Marlon Byrd to Triple A Albuquerque. |
| Purchased the contract of RF Scott Northey from Triple A Albuquerque. |
| Monday, April 7th, 1969 |
|---|
| Demoted SP Clise Dudley to Triple A Albuquerque. |
| Demoted RP Gary Dotter to Triple A Albuquerque. |
| Demoted RP Severino Gonzalez to Triple A Albuquerque. |
| Demoted C Brad Ausmus to Triple A Albuquerque. |
| Demoted RF Cody Ross to Triple A Albuquerque. |
| Purchased the contract of LF Dick Davis from Triple A Albuquerque. |
| Demoted LF Luis Silverio to Triple A Albuquerque. |
| Purchased the contract of RF Cody Ross from Triple A Albuquerque. |
| Monday, March 3rd, 1969 |
|---|
| Traded $1 in cash to the Brooklyn Dodgers, getting 27-year-old catcher Josh Willingham in return. |
| Invited non-roster SP Matt Garza to Spring Training camp. |
| Invited non-roster SP Mickey Haefner to Spring Training camp. |
| Invited non-roster SP Chad Gaudin to Spring Training camp. |
| Invited non-roster RP Al Hrabosky to Spring Training camp. |
| Invited non-roster 3B Phil B Clark to Spring Training camp. |
| Invited non-roster CF Marlon Byrd to Spring Training camp. |
| Invited non-roster LF Milt Bocek to Spring Training camp. |
| Invited non-roster LF Luis Silverio to Spring Training camp. |
| Invited non-roster SS Kevin Baez to Spring Training camp. |
| Saturday, February 1st, 1969 |
|---|
| Signed free agent RP Cam Bedrosian to a 1-year contract worth a total of $1,800,000. |
| Wednesday, January 8th, 1969 |
|---|
| Signed free agent C Eddie Kenna to a 1-year contract worth a total of $1,100,000. |
