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| Sunday, August 3rd, 1969 |
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| Signed free agent 3B Dean Palmer to a minor league contract with a $100,000 signing bonus. |
| Signed free agent LF Maurice Archdeacon to a minor league contract with a $200,000 signing bonus. |
| Signed free agent 3B Jonathan Villar to a minor league contract with a $400,000 signing bonus. |
| Signed free agent RF Pat McNulty to a 1-year contract worth a total of $2,200,000. |
| Signed free agent RP Bill Wertz to a minor league contract with a $75,000 signing bonus. |
| Signed free agent RP Tom Dozier to a minor league contract with a $65,000 signing bonus. |
| Friday, August 1st, 1969 |
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| Traded 35-year-old left fielder Ken Singleton, 33-year-old starting pitcher Lary Sorensen, 28-year-old minor league closer Chris Leroux, 27-year-old minor league second baseman Josh Barfield and 25-year-old minor league left fielder Jack Voigt to the St. Louis Cardinals, getting 30-year-old second baseman Wade Boggs in return. |
| Traded 29-year-old minor league center fielder Scott Northey to the St. Louis Cardinals, getting $1 in cash in return. |
| Traded 23-year-old minor league shortstop Glenn Hoffman to the Detroit Tigers, getting 31-year-old reliever Craig Kimbrel in return. |
| Traded 31-year-old starting pitcher Kirk McCaskill to the Milwaukee Brewers, getting $1 in cash in return. |
| Saturday, May 3rd, 1969 |
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| Signed free agent RP Dennis Powell to a minor league contract. |
| Signed free agent RP Dave Schuler to a minor league contract. |
| Thursday, May 1st, 1969 |
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| Traded 29-year-old left fielder Bob Elliott, 29-year-old minor league reliever Bill Dailey and 30-year-old shortstop Ed Romero to the New York Mets, getting 29-year-old minor league right fielder Scott Northey and $1 in cash in return. |
| Demoted CF Scott Northey to Triple A Mesa. |
| Purchased the contract of RP Bob Apodaca from Triple A Mesa. |
| Purchased the contract of SS Doug Flynn from Triple A Mesa. |
| Wednesday, April 9th, 1969 |
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| Signed free agent LF Ken Singleton to a minor league contract. |
| Signed free agent RP Andy Hansen to a minor league contract with a $10,000 signing bonus. |
| Wednesday, March 5th, 1969 |
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| Signed free agent RP J P Howell to a minor league contract. |
| Thursday, February 6th, 1969 |
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| Signed free agent 1B Jeff Conine to a minor league contract. |
| Saturday, February 1st, 1969 |
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| Traded 28-year-old catcher Miguel Montero to the Miami Marlins, getting 24-year-old minor league right fielder Jack Voigt in return. |
| Wednesday, January 8th, 1969 |
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| Signed SS Ed Romero to a 4-year contract extension worth a total of $7,000,000. |
