Answer
See below.
Work Step by Step
a) Chaplin was a man, an entertainer with an FBI file more than $2000$ pages long, thus he goes to V.
b) Einstein was a man, not an entertainer with an FBI file not more than $2000$ pages long, thus he goes to VII.
c) King was a man, not an entertainer with an FBI file more than $2000$ pages long, thus he goes to IV.
d) Roosevelt was a woman, not an entertainer with an FBI file more than $2000$ pages long, thus she goes to I.
e) Sinatra was a man, an entertainer with an FBI file not more than $2000$ pages long, thus he goes to VI.