Communication can be done in different ways; one of which is a condolence message. A person can communicate his feelings and express his condolences to the person who has suffered a loss of a loved one or something like that. Finding the right words to say when someone's mourning death can be difficult. The present study is an attempt to investigate the concept of condolences in certain messages given by the American President Barak Obama. It aims to: reveal the most frequent syntactic structure of expressive speech acts used in his condolence messages; find out Elwood's strategies used by Barak Obama. It is hypothesized that: declarative sentence is the most frequent syntactic structure of expressive speech acts used by Obama in the data under study and expression of sympathy is the most common strategy of Elwood's strategies that are used in these messages. The study develops an eclectic model of analysis based on syntactic structure of expressive speech acts and Elwood's 2004 strategies. Both of the hypotheses above are validated.