APPRAISER: You've brought an interesting archive, and we've singled out a few pieces here to tell a story I'm going to call, "Winston Churchill's Havana Connection." And what we have to start out with are two very nice portrait photographs of Winston Churchill, probably taken in the early '40s, early '50s. Beautiful signature in this instance, "Winston S. Churchill." Looking formidable, determined, unflappable, as he always did. This particular one is unusual because it's inscribed to Senora Giraudier.

GUEST: Right.

APPRAISER: Senora Giraudier was a relative of yours, I understand.

GUEST: Yes.

APPRAISER: Your great-aunt and great-uncle. What was their business?

GUEST: They started Polar Beer in Cuba, and they also had a tobacco plantation. This gentleman here is Tony Cuesta, and him and my great-uncle, Antonio Giraudier, had a tobacco factory. And interestingly enough, there's a portrait of Winston Churchill on the shelf there in the factory.

APPRAISER: Right.

GUEST: My great-aunt and my great-uncle striked up a friendship with Winston and Lady Clementine, and they would come to Cuba. They visited twice, and they stayed with them. And he would send Christmas cards and they would send cigars and brandy. After the years went by, they knew just exactly his particular brand of cigars and the brandy that he liked. And he was obviously grateful for the gift of good cigars.

APPRAISER: We found a letter of his secretary saying, "Your further consignment of cigars "arrived at the beginning of this week. "Mr. Churchill was here "when the stack of parcels were brought in, so we had to open them all under his eyes. He patted and purred with pleasure over them." This is a marvelous piece, too. "Your cigars reached Mr. Churchill safely and gave him much pleasure in Washington." My personal favorite in the archive is this letter here, which was written right after Churchill was elected for his final term as prime minister. It was a very troubled time, and he alludes to that in his letter. "To become prime minister of this country at the present time "is nothing to be overjoyed about. We are beset by difficulties." And I think that's a marvelous expression of his concerns about the fate of his nation and the free world in 1951. What we thought we would do is value the entire archive, which is full of letters, telegrams, postcards, pictures of the factory, ranging in date from 1949 all the way up to 1965, maybe beyond. I would value it for insurance purposes at $12,000.

GUEST: Wow. Thank you.

APPRAISER: It's a marvelous group of things, and it's wonderful you've taken such good care of them. Thanks for coming to ANTIQUES ROADSHOW.

GUEST: Phew! Yeah, thank you very much. Twelve thousand?

APPRAISER: Yeah.

GUEST: Wow.