APPRAISER: You shared an important part of your early life with the 44th president, Barack Obama, when you were a student.

GUEST: Sure, well, we were freshmen together at Occidental College in Los Angeles. And we were there for two years. We were in the same dormitory freshman year, and then, after our sophomore year, we both transferred to Columbia College in New York, and we were roommates for the first semester that we lived there in New York. And then after we both graduated, we stayed in touch. We wrote letters back and forth, and that's what I brought here, is some of the letters.

APPRAISER: That's great. And what was he like?

GUEST: Well, he was a very charismatic, fun guy. You could tell he'd be successful at something. Very thoughtful. I didn't see him as the first Black president of the United States, but I knew he'd be successful at something.

APPRAISER: Well, what I find fascinating about this group of letters, which includes seven postcards and three very lengthy handwritten letters...

GUEST: Mm-hmm.

APPRAISER: Is the two sides of Barack Obama, the, the man and the student, and then the idealist and the philosophy that he was building in these years. The letters date from the early 1980s to the late 1990s. To start with some of the, the later material first, I think this is a great card that he sent you, soon after he married Michelle, and he included a photograph of her with it.

GUEST: Right.

APPRAISER: And he wrote this little wonderful biographical comment: "I still have the nicotine habit, "but Michelle has made me promise to quit "as soon as the book is done. Otherwise, no babies."

GUEST: Right. That'd be "Dreams from My Father," the book that became a best-seller and helped, helped him in his career, yeah.

APPRAISER: That's right, that's right. And then, five years later, as his, he's ascending in his career, the, this letter gets very short. "Michelle and I have a beautiful baby daughter, "Malia, one year old. "I'm running for Congress. Life is hectic, but good."

GUEST: Right. As his life got busier, and became a senator and so on, his communications became shorter.

APPRAISER: In real estate, we all know the famous phrase about value: "location, location, location."

GUEST: Right.

APPRAISER: With letters and correspondence, it's "content, content, content." And in this letter is really where we see incredibly important content. This was written in November of 1985, five months after he became a community organizer in the South Side of Chicago. He talks about his work with his colleagues and as a community organizer, and his thoughts and his reflections on what was going on. He says, "I walk into a room "and make promises I hope I can keep. "They generally trust me, despite the fact that "they've seen earnest young men pass through here before, "expecting to change the world and eventually succumbing to "a lure of a corporate office. "And in a short time, "I've learned to care for them very much "and want to do everything I can for them. "It's tough, though. Lots of frustration when "you see a 43% dropout rate in the public schools "and don't know where to begin denting that figure. "But about five percent of the time, "you see something happening-- "a shy housewife standing up to a bumbling official, "or the sudden sound of hope in the voice of a grizzled old man "that gives a hint of the possibilities "of people taking hold of their lives, "working together to bring about a small justice. "And it's that possibility that keeps you going through all of the trenchwork." We all remember Shepard Fairey's campaign poster of, of Obama, that wonderful image of him with the word beneath it, "hope."

GUEST: Yeah.

APPRAISER: And here it is, "hope."

GUEST: Right.

APPRAISER: Not only do we see the word "hope" in this letter, but we see "love," and others of the postcards and letters are signed "love." These are two very simple, very basic four-letter words, and they show him in his formative years as he's developing what would evolve into his presidential politics. And I think that that's an amazing resource for us biographically to, to kind of understand his mindset in, in these early years.

GUEST: I did visit the White House in 2011. It was nice to go to the Oval Office and hang out for what turned out to be 15 minutes, so that was pretty exciting.

APPRAISER: In terms of putting on a value of letters like this, it's hard, because from a biographical point of view, there, there's endless value. It's very, very rich. Letters have come on the market, but nothing of, of this kind of caliber. This letter alone, I would give a fair market value of $8,000.

GUEST: Wow, that's a lot.

APPRAISER: All together, I would give the entire group, the seven postcards and the three letters, a fair market value of $25,000.

GUEST: Mm, wow.

APPRAISER: And in terms of insurance, I think you should think of them in the range of about $40,000.

GUEST: Okay. I'm interested in preserving them as historical documents. It's good to have an appraisal and have some idea of what they're potentially worth.