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| Thursday, November 6th, 1969 |
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| SP Jack Hallett retires. |
| Friday, August 1st, 1969 |
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| Demoted SP Ryan Jensen to Triple A Memphis. |
| Demoted 1B Harley Boss to Triple A Memphis. |
| Demoted SS Yuniesky Betancourt to Triple A Memphis. |
| Traded 30-year-old second baseman Wade Boggs to the Chicago Cubs, getting 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 in return. |
| Traded $1 in cash to the Chicago Cubs, getting 29-year-old minor league center fielder Scott Northey in return. |
| Demoted LF Jack Voigt to Triple A Memphis. |
| Demoted CF Scott Northey to Triple A Memphis. |
| Tuesday, July 1st, 1969 |
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| Demoted RP Jon Switzer to Triple A Memphis. |
| Purchased the contract of SP Ryan Jensen from Triple A Memphis. |
| Friday, May 16th, 1969 |
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| Demoted C Tom Murphy to Triple A Memphis. |
| Purchased the contract of 2B Boyd Bartley from Triple A Memphis. |
| Monday, April 7th, 1969 |
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| Purchased the contract of RP Jon Switzer from Triple A Memphis. |
| Purchased the contract of SS Dave Concepcion from Triple A Memphis. |
| Purchased the contract of CF Peanuts Lowrey from Triple A Memphis. |
| Wednesday, February 5th, 1969 |
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| Signed free agent RP Ed Whitson to a 1-year contract worth a total of $1,700,000. |
| Wednesday, January 1st, 1969 |
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| Purchased the contract of SP Ed Correa from Triple A Memphis. |
