Bob Mankoff considers the phrase "think outside the box," and he and his assistant, Colin, peer inside a box of Donald Trump-themed items.

The cartoon ran not before the current crisis, it ran in 1927 during the bubble that led to the Wall Street Crash of 1929. A month after the crash, a cartoon has "a woman giving money to a vagrant.

Today, Mankoff speaks to Tom Power about his career, how he views the art form as "thinking through drawing," and how he tackled the most recent U.S. election through cartoons.