Scene 1: Fortune
1. What would Machiavelli say about the opening quote of this film,
"New York, it can destroy you or fulfill you depending a good
deal on luck"? Were Machiavelli alive today, and a citizen
of the United States, would he choose to live in New York City or
Washington, D.C.? Where do you think the greater opportunities lie?
2. Addresses his fellow Athenians, Socrates refers to Athens as
coming from "the greatest city" in the world. How does
New York City differ from Athens, as it appears in The Apology
Scene 2: Deal Making
1.The Mayor of New York and a party boss named Frank Anselmo are
making a deal in this scene. Do they strike you as friendly or adversarial?
Or both? Explain your answer.
2. Frank refers in this scene to the Mayor's boy, Kevin Calhoun,
whose voice we hear in the first scene. Would Kevin be pleased to
hear of himself referred to as "the Mayor's boy"?
3. What is Frank hoping to get from the Mayor in this scene? What
is the Mayor hoping to get from Frank? Do they each succeed?
Scene 3: Menschkite
1. In this scene a distinguished Judge is implicated in some wrongdoing.
The judge is a friend of the Mayor. Kevin's advice to the mayor
is to "put some distance" between himself and the judge.
What does he mean by that? How would they go about doing such a
thing? Why is it that the Mayor refuses to follow Kevin's advice?
2. How would you explain what the Mayor means by "menschkite"?
Do you admire the Mayor for the importance he places on "the
stuff between men"? Or do you think him foolish?
3. Whose position would Machiavelli back in this scene, Kevin's
or the Mayor's? Explain the reasons for your answer.
4. Does the idea of "menchskite" make some sense of the
exchange between Frank Anselmo and the Mayor in scene 2? Explain.
Scene 4: Politics as a Disease
1. Although Kevin claims that "there is something special
about small town life," he is in New York by way of Washington.
Explain Kevin's answer to Mary Beth's question, "What are you
doing in New York?" What does it mean to "catch politics
like a disease"?
2. Kevin says that working for the Mayor, he has found a position
in government where he can "make a difference." What does
that expression mean? What does Kevin hope for from politics?
3. Mary Beth tells Kevin that he has made a difference, to the
wife of Eddie Santos. That is not enough for Kevin - he wants to
see how far the corruption in this scandal leads. He is willing
to risk the officer's name and pension for that. Does he do the
4. Is it at all Machiavellian for Kevin to threaten the "full
weight of the Mayor's office" to keep Mary Beth from jeopardizing
the outing of the full truth?
Scene 5: Menschkite revisited
1. It seems Kevin has learned something about the Mayor since the
last scene. What do you think it is?
2. Why do you suppose the city has lost its bid for a political
3. Frank Anselmo has shot himself, because he was so deeply implicated
in this scandal. Once again, as was the case in Scene 3 with Judge
Walter Stern, Kevin and the Mayor revisit "menschkite,"
because the Mayor wants to go pay his respects to Frank's widow,
and Kevin is worried about the "perception." Is Kevin's
Machiavellian advice - worry about appearances? Why or why not?
4. What is the Mayor's initial response to the breadth of this
scandal, which reaches all the way to him? Why isn't Kevin "bursting
with admiration" for Mayor's readiness to turn "adversity
into triumph"? What does he know better?
5. Why does the Mayor say, "don't fathers listen to their
sons?" Why does the Mayor, John Pappas, call Kevin, Pappy?
6. Is "menschkite" "horseshit," as Kevin says?
Is it all about political corruption? If not, where is the line
one cannot cross? Where does the grey end and the black begin?
7. Are there shades of grey here that Kevin does not recognize?
Or is the Mayor deluding himself?
8. Why does Kevin insist that the Mayor "take himself out"
1 . What does the movie say about power and morality? Does this
movie confirm Machiavelli's teaching that the man who wants to make
a profession of good in all regards will come to ruin among so many
who are not good?. Does the film add something to Machiavelli's
2.Compare the relationship between Elizabeth and Walsingham to
that between Kevin and the Mayor. What does each learn about politics
from the older and more experienced practitioner?
3. Compare the relationship between the Mayor and Kevin to that
between Sonny and C. How does the protege of each transcend his
4. Compare Kevin in City Hall to Henry in Primary
Colors. Is City Hall more hopeful about politics than
Primary Colors? If so, on what grounds does it reach a
5. How does City Hall address Socrates' reservations
about political life? Does it agree or disagree with Socrates about
what one can expect from politics?