GUEST: I brought some silk boxer shorts that John F. Kennedy left in our house.

My father was a prominent politician in Indiana.

He got very involved in JFK's presidential campaign.

In October of '59, Kennedy came through our hometown in Southern Indiana, and my dad created a big fundraiser for him.

Kennedy needed a place to stay for the day, and so he stayed in our house.

He was battling a very sore back, apparently.

So he bathed in our upstairs bathroom.

After the whole event was finished and he left town, my mom found these boxer shorts on the bathroom floor.

Apparently, he forgot them.

APPRAISER: In 1959, Kennedy was the junior senator out of Massachusetts, and he wouldn't declare his official candidacy for the presidency, even though it was expected, until January of 1960.

APPRAISER: But as you said, in the fall, he would have been traveling around America, continuing to lay the groundwork for his candidacy, getting ready for the primaries, and meeting important Democratic supporters and fundraisers, of which your father was one.

GUEST: Right.

APPRAISER: I had a chance to take a look, and on October 4, 1959, in your hometown of Huntingburg, Indiana... GUEST: Right!

APPRAISER: ...it was a hot fall day.

It made it to 88 degrees.

GUEST: I did not know that.

APPRAISER: He had events to go to, a lot of standing.

He then retired to your family's home.

So, your father was sort of his host.

APPRAISER: And where he could cool off.

And who hasn't left things behind as a guest?

GUEST: Right.

APPRAISER: This is a pair of silk or synthetic undershorts.

There's a store label from Lewis and Thomas Saltz and Company from D.C., and they were a very prominent haberdashery, menswear, in Washington, D.C., serving all the politicians and businessmen.

On the inside front of the waistband is also some block letters in a permanent ink that say "K-E-N-N."

GUEST: Mm-hmm.

APPRAISER: I imagine that's from the junior senator having his clothes sent out to a laundry.

And you've also bought a photo of Kennedy.

In your family home?

GUEST: It is our family home, he's standing on the stairwell, and he signed it to my parents.

APPRAISER: The best kind of provenance is when the individual who's a historic person has given it to a trusted confidant or if it's from the family of the historic person.

And we don't have that-- we don't have... We don't have a picture of JFK giving these to your mom.

What we do have is a meticulously documented history.

And also it's documented in two books.

GUEST: One book was written about my father.

In it, the story is described just as I told you.

GUEST: Then there's another book, the history of Huntingburg itself, and the same story is described there.

So apparently, in that book, it said that my father wrote him a humorous letter saying, "Well, if you're accustomed to leaving your boxer shorts around the country, maybe you need another pair," so he sent him a new pair.

APPRAISER: That is utterly charming.

GUEST: And that's my dad's sense of humor.

APPRAISER: Kennedy's special.

GUEST: Yes, he is.

APPRAISER: The idealism, the charisma, and the social impact of the president and his family.

For auction purposes, we'd put an estimate of $3,000 to $5,000.

GUEST: Yeah, that's nice.

(both chuckle) APPRAISER: This is probably about $500 itself, but it is helping to verify, uh, the story.

APPRAISER: And so these kind of need to be kept together.

For insurance value, I would have $10,000... GUEST: Mm.

APPRAISER: ...on these.

The, the collection, yeah.

GUEST: Okay.