The poster is a Memphis Chicks Schedule poster from the late 1980's or early 1990's (notice the Chicks patch on the left sleeve). I had one in my room during that time period. Once people noticed the poster on Seinfeld they were for sale all over town.
Hope this helps... but pretty sure it does not depict Barack Obama (he would have been a first year law student at Harvard around the time it was issued)
Good Luck tracking one down - - -
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