Desmond's letters refers to a box of letters that Desmond wrote to Penelope Widmore while he was incarcerated at Southway Garrison. After being released from prison and dishonorably discharged from the Royal Regiment of Scotland, it was revealed that Penelope's father, Charles Widmore had intercepted all of the letters. He then returned them to Desmond in a box as he attempted to bribe Desmond into ceasing all further contact with his daughter. ("Live Together, Die Alone")
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- Desmond's letters
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| - Desmond's letters refers to a box of letters that Desmond wrote to Penelope Widmore while he was incarcerated at Southway Garrison. After being released from prison and dishonorably discharged from the Royal Regiment of Scotland, it was revealed that Penelope's father, Charles Widmore had intercepted all of the letters. He then returned them to Desmond in a box as he attempted to bribe Desmond into ceasing all further contact with his daughter. ("Live Together, Die Alone")
- After Desmond was released from his imprisonment and then dishonourably discharged from the Royal Scots Regiment, he was met by Charles Widmore outside the Southway Garrison. Desmond entered his car and was told that he had two present for him, one containing his past, the other his future. Desmond opened the first box only to find all the letters that he had written to Penny during his imprisonment. The other box he opened contain a large sum of money for "his new life".
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| - The box of letters revealed by Charles Widmore.
- Desmond thumbs through a stack of letters from the box.
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| - After Desmond was released from his imprisonment and then dishonourably discharged from the Royal Scots Regiment, he was met by Charles Widmore outside the Southway Garrison. Desmond entered his car and was told that he had two present for him, one containing his past, the other his future. Desmond opened the first box only to find all the letters that he had written to Penny during his imprisonment. The other box he opened contain a large sum of money for "his new life". When Penny arrived in Los Angeles and confronted Desmond, she inquired as to why he didn't write her while he was in prison. Desmond changed the subject to her upcoming marriage, and did not reveal that it was her father who had prevented the letters from getting to her.
- Desmond's letters refers to a box of letters that Desmond wrote to Penelope Widmore while he was incarcerated at Southway Garrison. After being released from prison and dishonorably discharged from the Royal Regiment of Scotland, it was revealed that Penelope's father, Charles Widmore had intercepted all of the letters. He then returned them to Desmond in a box as he attempted to bribe Desmond into ceasing all further contact with his daughter. ("Live Together, Die Alone") Later, when Penelope discovered Desmond's location and confronted him, she asked why he didn't write to her while in prison. Desmond did not reveal that he had, but that her father had taken all of the letters.
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