| # | Clue | Answer As Given | Value | Round | Category | Air Date | Show |
|---|---|---|---|---|---|---|---|
| The Times felt "Grand Illusion" failed to be the definitive, nuanced portrait of this man, "America's Mayor" | Rudolph Giuliani | $400 | DJ | THE NEW YORK TIMESBOOK REVIEW | 2007-04-23 | #5216 | |
| Follow along as New Yorker Tony Roberts reads this former mayor's book "Leadership" | Rudolph Giuliani | $600 | J | BOOKS TO LISTEN TO | 2003-06-23 | #4346 |