Peter Kasperski, the iconoclast behind many of Scottsdale’s best restaurants, matches wines with fabulous Japanese, Italian and Mexican–inspired recipes.

When restaurateur Peter Kasperski arrived in Scottsdale, Arizona, in 1979, he had at least one good reason: to escape the Chicago winters. “The year I shoveled snow off my roof so it wouldn’t collapse was the year I moved.” In 1997, he made another good decision: to open a restaurant that would help Scottsdale realize its potential as a great food town.

Along with partner Marianne Markogianis and chef Bernie Kantak, Kasperski launched Cowboy Ciao, a quirky neo-Western restaurant. To pair with dishes like buffalo carpaccio, he compiled an eclectic 88-selection wine list. During the restaurant’s first week, two supermodel types came in and delighted him by ordering a blend of Negroamaro and Malvasia Nera from Apulian vintner Cosimo Taurino—affirmation that Scottsdale was ready for something more ambitious.

Kasperski planned to expand his list to 100 bottles, but things got out of hand. Today he presides over a cellar of 28,000 bottles, with 3,300 labels from 45 countries. And the cellar keeps growing: It got too big “about 2,000 bottles ago,” he quips. This one cellar provides all the bottles for the seven wildly diverse restaurants in Kasperski’s mini empire. A diner at any of his restaurants can order off the same enormous, ever-changing list, with bottles sorted not by varietal or region but by color and price. Champagne is next to aged sparkling wine from California’s Livermore Valley; Bordeaux shares space with Bulgarian Merlot; Mexican Zinfandel is grouped with Côtes-du-Rhône. Kasperski contributes Tom Robbins–esque tasting notes. He describes Zilavka from Herzegovina’s Mostar Vineyards, for instance, as a “light-bodied white added to the list in honor of Superman’s most mischievous opponent, Mr. Mxyzptlk.”

Organizing the list by price is Kasperski’s trick for getting people to try wines that are out of their comfort zone. As he says, “For every five people who come in knowing they want a Cabernet, there are another 15 people who know they want to spend $50, and they want the best wine experience they can have for $50.”

Since opening Cowboy Ciao, Kasperski has launched Kazimierz World Wine Bar, a speakeasy-style restaurant (there’s no sign, the entrance is in the back and the kitchen is open until almost 2 a.m.), and the Japanese-style Sea Saw with Nobuo Fukuda (an F&W Best New Chef 2003). And this year he has added two more places, Mexican Standoff and Digestif, in Scottsdale’s tony new SouthBridge development, an urban “village” along the waterfront (actually, an irrigation canal) with town houses, shops and restaurants. SouthBridge also serves as a new home for Sea Saw and its casual new offshoot, Shell Shock. All that’s left now is for Kasperski to figure out how to move bottles of wine from his cellar to any of his venues in 10 minutes or less. “We’re going to get a couple of Segways,” he deadpans.

Kasperski grew up some 50 miles northwest of Chicago. At age 12, he started working as a dishwasher and busboy to earn gas money for his boat (with which he commuted), and to avoid a job in his father’s construction business. Eventually he made his way to well-known restaurateur Sasha Vereschagin, the Russian-born owner of Dining with Sasha. Vereschagin was obsessed with sourcing unusual wines and liquors, and he gave Kasperski his first “mind-blowing” experience tasting old Burgundy. (A Cowboy Ciao house shot, the Nikolashka, also originated with Vereschagin.)

When it comes to pairing wine and food, Kasperski’s approach is like free association with a corkscrew. Consider the wine choices at Mexican Standoff, where Kantak blends Mexican, Brazilian, Colombian and Guatemalan influences. To match spice rubbed rib eyes with lime butter, Kasperski might avoid the obvious wine partner, Cabernet, in favor of a floral- scented, beef-loving Malbec from Argentina. Or he’ll pair a complex ceviche not with the usual Sauvignon Blanc but with honeysuckle-inflected Viognier, or even red Gamay. “There are so many components to the ceviche and so many interesting things going on,” he says. “It’s hard to make a pairing mistake.”

Nowhere are Kasperski’s beliefs about food and wine on better display than at Sea Saw and Shell Shock. Fukuda, a traditionally trained Japanese chef, is a devoted wine collector who never creates a dish without a pairing in mind. Even at home, he’ll match sea urchin and Pinot Noir—a pairing that astonished him when he first tried it. Fukuda was working at Scottsdale’s Hapa when Kasperski noticed that this former ski-patrol medic was a kindred spirit. Fukuda’s keen sense of how to mesh disparate ingredients like grilled octopus, mozzarella and wasabi aioli jibed perfectly with Kasperski’s rules-be-damned wine approach.

Today, the two men spend their days parrying over pairings. Fukuda lobbies for subtle Old World choices—Burgundy in particular, but also German and Austrian wines. Kasperski pushes bolder New World alternatives and esoterica like Campanian Aglianico. For a dish like his lovely oven-steamed bass with wild mushrooms, Fukuda gravitates toward earthy Burgundy, while Kasperski counters with a fruity California Pinot Noir rosé—same grape, different package.

Ultimately, Kasperski is game for some competition in Scottsdale. For one thing, he hopes the long liquor list at Digestif will inspire fellow restaurateurs to dump the soda guns and sour mix and start training bartenders to serve properly made sidecars and Negronis. “I really want a bar that I don’t own where I can go drink.”

Jon Bonné is the wine editor of the San Francisco Chronicle.