GUEST: We have, uh, several items from my great-great-uncle, Eugene Woodruff.

He was an 1866 graduate of West Point.

And, uh, we have his class ring, uh, his, uh, kepi and, uh, gauntlets.

And this is a photograph from his, uh, annual yearbook.

APPRAISER: Are there any markings on the ring?

GUEST: Uh, yes.

It's a, a wax sealing ring.

APPRAISER: That explains why the 66 is backwards.

GUEST: Is backwards, yes.

APPRAISER: Right.

And what about the, the flag here?

GUEST: The flag is a presentation piece that was given to, uh, Eugene Woodruff on the 4th of July in 1873, uh, by the people of Shreveport in appreciation for his work in removing the Great Raft of the Red River, which is a 40-mile log jam that the government had been fighting with for, uh, 40 years.

He was the engineer in charge of the project and he was finally able to successfully remove it.

He used, uh, the latest technology in doing it.

He, uh... uh, he used new steam equipment that hadn't been available before, and, uh, nitroglycerin, which revolutionized the, uh, job of removing, uh, obstructions in rivers.

APPRAISER: (chuckling): I'm sure it did.

GUEST: Yeah.

So... APPRAISER: Well, he graduated from West Point in 1866 at the end of the American Civil War.

Um, he did not see combat.

But what a lot of people don't think about is the fact that, after the war, there were things like the log jam.

There were things that needed to be reconstructed.

And he graduated as an engineer.

And you have his kepi, um, the eagle or the wreath on the front.

Um, the... it's missing the "U.S." Uh, it's got great Engineer Corps buttons on, on each side.

Uh, great cap.

The flag has 37 stars, uh, which fits in with the time frame that's written on the flag.

And one of the things that caught my eye first was this great pair of gauntlets.

They're entirely hand sewn.

You can see all the tiny little stitching, uh, from the glover that made them.

But on the inside, they're also named to him where he, he had them stamped with his name and "U.S.A." A wonderful pair of gloves.

And so, uh, where did you get the image?

GUEST: The, uh, class photo we actually got online.

Uh, it came from the yearbook that was published that year and it was floating around.

I just happened to catch it.

APPRAISER: Wow.

GUEST: And I paid $30 for it.

APPRAISER: Wow.

GUEST: He signed it and, uh, put his address, "Independence, Iowa," on the, uh, on the picture there.

APPRAISER: Right.

Have you ever had any of these items appraised before?

GUEST: No.

APPRAISER: So, for the items that we have here, we would put an insurance value of, uh, $15,000 on it.

GUEST: Really?

APPRAISER: Yeah, it's...

GUEST: Well, okay.

(chuckles) APPRAISER: Well, there, there's some really rare and interesting things.

You know, the ring, obviously, um, but the other items are fantastic also.