Every time I enter my house, the metalwork sculpture that hangs above our bar taunts me.

Don’t get me wrong: I like the piece my wife, Jen, refers to as the Labyrinth, an impulse buy my in-laws made at the bookstore Kroch’s and Brentano’s back in 1969. But whenever Jen and I have moved, there’s been no room for discussion: This hunk of bronzed steel must be the centerpiece of our home.

Meanwhile, she relegates my favorite family heirlooms—a trio of gold-framed oil paintings that belonged to my grandma Pearl—to a remote, semihidden location. At the condo, she shoved them atop our kitchen cabinets, alongside a plastic pig and a framed puzzle of a block of cheese. Currently, they reside in a basement closet next to my picture of Mike Ditka giving the finger (also unworthy of our walls).

We’re big fans of Antiques Roadshow, the PBS staple where people find out if there’s gold in Great-Aunt Edna’s old Hummel figurine collection. Sometimes when we’re watching, I argue that my grandma’s Italian street scenes deserve a more prominent position. “They must be valuable,” I insist, despite having no basis other than that I like them. Jen dismisses my ramblings and brags that the Labyrinth is surely more valuable and, thus, deserving of its place of honor. Boom! It’s on. Marital smackdown.

To finally call a winner—but mostly to prove I am right—I head to Leslie Hindman Auctioneers in West Town for a personal Antiques Roadshow. I arrive on a good day. The esteemed house is previewing its modern design auction. Midcentury decor that looks straight out of Don Draper’s bachelor pad packs the backroom. I spot chairs and end tables that would’ve fit right in at Grandma Pearl’s crib. Excellent. Then I spy a few pieces of vintage wall art that remind me of the Labyrinth. Uh-oh.

Within a few minutes, I meet the pair of 30-ish dudes who will appraise the junk currently in my trunk. Both look like they were born to work in the auction business. Corbin Horn, the furniture and decorative arts expert, is tall and trim with excellent posture. Next to him is Zachary Wirsum, a fine art specialist who happens to be the son of painter Karl Wirsum, a member of the legendary Hairy Who. With his Duck Dynasty–style beard and oversize topcoat, he looks like he traveled from the 1890s to analyze your Frederic Remington.

In addition to handling estate sales for well-to-do folks, auction houses replenish their inventory by catering to clueless walk-ins like me. “We get a lot of dumpster divers,” says Horn.

“But we also get great things that walk through the door unexpectedly,” adds Wirsum. “Often, it will be someone who has no idea who the artist is, but we immediately recognize it. I would say one out of 10 ends up being something pretty exciting.” Exhibit A: the unassuming fellow who marched in with a painting by a well-known 19th-century artist under his arm. They conservatively estimated its value at $10,000 to $15,000. It ultimately sold for $50,400. (Even with the auction house taking its cut—typically around 25 percent of the sale price—the guy got a sweet payday.)

But what about people who come in with stuff that’s worth nothing? Are they let down easy?

“A good canned response is ‘You should keep that. It probably has sentimental value,’ ” says Horn. He lowers his voice. “Or we’ll say, ‘There’s not really a good market for it right now,’ which is being perfectly honest.”

It’s appraisal time, and I feel an adrenaline rush as we squeeze into a small conference room. Leslie Hindman, 63, an elegant blond woman dripping with expensive-looking gold jewelry, joins us. I show her my grandma’s paintings.

“I like them. They are kind of retro-looking,” she says. But then she spots the Labyrinth from across the room and is immediately intrigued. “Now what is that?” she asks. “That’s cool. Do you know who made it?”

“That’s a Curtis Jeré,” Wirsum says. He points to a tiny signature inscribed on one of the panels. “At first I thought it was a knockoff, but it’s a real Jeré.” He sounds increasingly excited each time he says the name, which he repeats over and over. Evidently, the designers are kind of a big deal in the Brutalist movement of the 1960s and ’70s. Brutal is right.

Scrolling through an iPad, he shows me a listing for a similar Jeré piece that features descriptors such as “wonderful,” “iconic,” and “rare.” He estimates a value of $800 to $1,200 for the Labyrinth.

Huh. I’ll be damned. Still, I hold out hope that my paintings will fetch even more. I present them to the experts with a big smile, stretching my arms out like I’m Vanna White.

Wirsum flashes me a sad-face look. “I think your wife is going to win,” he says. He has to look up the Italian artist who painted them: Carlo Ciappa, whose work straddled the 19th and 20th centuries. Wirsum struggles to find much about him online. But when he does locate other Ciappa works sold at auction, some are listed at upward of $1,500. Score!

He deduces that mine are from the mid-1900s, later in the artist’s career. Practice makes perfect, right?

“I think earlier on, he was painting these more realistic scenes with a little more detail,” Wirsum says. “And in keeping with the times, he probably simplified and abstracted the forms to do these street scenes. His earlier work is probably worth more.”

Great. I scored late-era Ciappa, when the guy was phoning it in. OK, let’s get this over with. What are they worth? “I’d say $500 to $700,” says Wirsum.

Each? “No, that’s for the trio,” he says. Well, shoot.

I thank the appraisers for their time. But on the way home, I decide to get a second opinion. Cash America Pawn on North Avenue in Wicker Park doesn’t have any fine art on its walls. But if you’re looking for season 2 of Dawson’s Creek on DVD for 50 cents, this is your place. The manager, a polite, burly guy dressed all in black, takes a long look at my paintings.

“To be real honest with you, this is something I’m going to have to take a pass on,” he says. Then he reconsiders and makes an offer: 15 bucks. “Sorry, man,” he says. “There’s really not a good market for these.” Ouch.

He delivers a final blow: Customers are more interested in other subjects, like dogs playing poker. “People will always buy that.”

Sure, but getting those puppies on the wall of your house is another matter.