A 1912 novelty Teddy Roosevelt game is among the most intriguing offerings in Heritage Auctions’ sale of the Frent Collection on October 21.

Wacky political memorabilia isn’t just a feature of modern elections.

It turns out people have been at it for years.

Teddy Roosevelt ran for the independent Progressive Party in the 1912 US election

In 1912 (three years after he was ousted as president), Teddy Roosevelt put himself up for the Republican ticket but was passed over.

So he decided to start his own movement, the Progressive Party – also known as the Bull Moose Party.

He ultimately lost out to Democrat Woodrow Wilson.

The novelty item was made to promote Roosevelt's campaign. It's constructed from cardboard, with a pair of pince-nez made of metal and glass.

The idea is to try and get two balls in the centre of each eye.

The writing under his chin reads: “The Teddy Sideways glance makes the political bosses dance.

“To do this little stunt, make his eyes look straight in front. Then you'll vote and I'll vote and with other votes galore we'll land the Bull Moose President within the White House door."

The design is extremely rare.

In fact, Heritage states it’s the only example it has ever seen. Two others were created in 1908 for the William Taft and William J Bryan campaigns.

Of the three, the Bryan is the most common – with three known survivors. One of those made $8,000 in a recent sale.

Heritage Auction estimates the Roosevelt at somewhere in excess of $2,000. It describes it as “one of the Frents’ favorite items in the collection and understandably so.”

The sale will also include a remarkable letter from Ulysses S Grant that totally changed the direction of the US Civil War.

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