GUEST: This has been in my family for four generations.

My grandfather got it from his father.

My mother gave it to me.

But the person I associate most with this is my grandfather.

He was a big water person.

He was a swimming coach, a lifeguard, and then he was in the Navy.

This is his favorite piece.

APPRAISER: It's a great piece of folk art.

It isn't by any known maker, but that's the nature of folk art.

This is what's called a shadow box picture.

And what it is depicting is the America's Cup race, which is an enormously prestigious race, initially between the United States and Great Britain.

And the fact that an American ship could beat the British at their own game was like the Revolutionary War all over again.

The first victory of the Americans over the British was in 1851, and it was won by the ship America.

This was a victory that happened in 1885, where the Puritan triumphed over the British.

Now, the Puritan has an association to Boston because it was owned by John Forbes.

Not the New Jersey Forbes of Forbes Magazine, but enormously wealthy, very successful Bostonians.

This became a subject of legend and something that motivated folk artists to memorialize.

This was made probably pretty close to the actual event.

It could have been anywhere from 1885 to 1900.

The background is probably artist board.

The sails are made from paper that's been sort of sewn and appliquéd onto the mast and the sails.

And there are these figures on the deck, and they're just adorable.

And they're probably paper cutouts that have been painted and sprinkled with mica so they sparkle.

And the neat thing is the sea, which is this sort of crinkled paper or composition that has been manipulated in such a way that when it's painted, it looks like the choppy seas that the Puritan would have been traveling in.

Beyond that, you have the legend here, "Winner of the American Cup."

Should be "the America's...

GUEST: Yes.

APPRAISER: ...Cup."

And I can only tell you that the guy who did this was so enthusiastic about doing it that his enthusiasm overtook his dictionary.

So it's just a really charming, vibrant, exciting piece.

And the consensus is that something in the range to, of $4,000 to $6,000...

GUEST: Oh, my gosh.

APPRAISER: ...would be an auction estimate.

GUEST: That's fantastic.