Every time the subject of their relationship comes up, they swivel in their chairs to face each other, grinning and batting their lashes. If confronted with a question they aren’t sure how to answer, each stares at the other, as if attempting some form of telepathic communication.

That Griffin has a reputation on Wall Street as somewhat of a taskmaster makes his transformation into a marshmallow around his wife even more remarkable. When asked whether it was difficult to woo Dias, considering she lived in New York at the time of their courtship and he was in Chicago, Griffin flushes and says, "Oh, yes."

"Yeah, given I’d been to Chicago only twice in my life for a few hours each," Dias pipes up with her French accent. "He was very smart. He proposed before the winter. In the fall."

When asked if she had already been persuaded to move to Chicago, Dias says, "That pretty much convinced me!" They both break out in cascades of laughter.

Dias is largely credited with bringing cultural sophistication to the marriage, though Griffin had more than dipped his toe into the art world before she entered the picture. One afternoon during a business trip to New York in 1999, Griffin wandered into Sotheby’s auction house in Manhattan. He became electrified by a bronze cast of a sculpture by Edgar Degas called Little Dancer, Aged 14, which drew him into a 40-minute discussion with Diana "Dede" Brooks, who was then Sotheby’s C.E.O.  Griffin, all of 30 years old, would later end up buying not only a version of that piece but another Impressionist work as well, a Degas pastel titled Dancers in Green. He also went out and bought himself a water lily painting by Claude Monet.

Griffin’s interest in Impressionism is the source of a long-standing joke between him and Dias. During the

early months of their relationship, she had dismissed Impressionism as an artistic movement she "outgrew" as a teenager. When she visited Griffin in his Chicago apartment for the first time, she was stunned to find several museum-caliber examples of hard-core Impressionism. "We had a good laugh," Griffin says.

Since those first purchases, the couple has assembled a collection of about eight pieces, some of which have historical significance. In 2004, ArtNews included Griffin and Dias among the 10 most active art buyers in the world, alongside Cohen and other more established collectors such as Eli Broad and Ronald Lauder.

That designation came after the couple added Curtain, Jug, and Fruit Bowl, a still life by Paul Cézanne to their holdings—they bought it for an undisclosed sum from casino baron Steve Wynn’s private collection—as well as an 1895 Cézanne self-portrait.

Thanks in part to the Griffins’ donation, the Art Institute of Chicago recently broke ground on an ambitious new wing for Modern art, designed by architect Renzo Piano. The new building will include a grand, double-height glass-enclosed hall called the Kenneth and Anne Griffin Court.

In his bid to become a modern-day Astor, Griffin has left little to chance, pursuing his outside interests with the same zeal he applies to his business. It should come as no surprise, then, that a rumor has circulated for some time that he’s contemplating running for the Senate, most likely as a Republican, in 2008.

When asked to articulate his political philosophy, Griffin slips into an extended silence and exchanges a meaningful gaze with his wife. "Both parties have moved so far—so close to the center across so many issues. It’s hard to tell who’s what anymore," he says.

The couple are active donors within the Republican Party, Federal Election Commission records show, and Griffin was an enthusiastic supporter of George W. Bush in the past two presidential elections. He and his wife have also made campaign contributions to Democrats, including Illinois representative Rahm Emanuel. Griffin says that he and Dias will be "involved" in Illinois senator Barack Obama’s presidential campaign but will not go so far as to say that they plan to throw their full support behind him.

Griffin is reluctant to directly address rumors of his own senatorial aspirations. When asked if running for office is something he has considered, he looks at his wife, who responds in a high-pitched voice, "Me?" They both laugh nervously.

"There’s your answer," Griffin says. "No. She said no," he continues. "We’re partners."