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Last onths Rent & Security Deposit

Question for a friend: A tenant moved in Aug 3 08, and signed a 1 year lease that expires Aug 3 09, He paid First, Last & Security Deposit, Rent is $1,199.00 a month & security was to be $1,199.00 as well, he only paid $600.00, with a verbal promise to pay the rest but never did, but did collect in total $2,998.00. with all monies combined. On the lease it shows he paid a security deposit of $1,199.00 but does not show that he paid last months in advance. After he signed it, then last months rent was paid so it is not written in the contract.  He emailed a notice that he was leaving somewhere between May & July which broke the lease and he moved out June 29, 09.  With that being said, my friend rely's on the rent she receives to pay her mortgage, plus there were some damages minor when he moved out and the house had to be cleaned. It was filthy.  Questions: Is he entitled to his last months rent he paid in advance?  Is he entitled to all or partial of the security deposit?
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Generally, you may deduct all unpaid rent, charges and physical damages from any deposit or pre-paid rent.
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