Image Description:

Illustration depicts William Jennings Bryan, the 1908 Democractic candidate for president, behind a mask of his own face. The mask shows text such as “The Conservative Bryan” and “The New Bryan”. Signs on Bryan's pants depict common themes of his campaign such as the government ownership of railroads, the free silver movement, populism, and anti-imperialism. A toy donkey peers beneath the mask at the real Bryan saying “I know who it is.” The toy donkey is being held on a string by Miss Democracy who is dressed like Little Bo Beep and carrying a staff. Miss Democracy questions Bryan “Are you sincere? You gay deceiver.”  

As the title, “A HALLOWE’EN PARTY. NEARLY TIME TO UNMASK, WILLIE” suggests, at the time the 1908 presidental election was just days away.  The artist of the cartoon is Fred Morgan and it was printed in the Philadelphia Inquirer on 10-31-1908.
 

Inscription:

I'm fooling them all (William Jennings Bryan)

Are you sincere? You gay deceiver (Miss Democracy)

The Conservative Bryan
Anything to win
Heores
SMS
The friend of labor
Bogus labor plank
Promises promises
The New Bryan
  (Mask)

Govt ownership of railrds
Anti imperialism
Free silver
16 to 1
The old Bryan
Populism
Initiative and referendum
  (William Jennings Bryan's clothes)

I know who it is (Toy donkey speech bubble)

Dem. Party (On toy donkey)

MISS DEMOCRACY (Dress)

Fred Morgan (Signature)

Phila Inquirer 10-31-08 (Handwritten note)

A HALLWE'EN PARTY. NEARLY TIME TO UNMASK, WILLIE (Bottom text)