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In the offices of the Hennessee Group hang two oil paintings and two prints, each portraying the bespectacled visage of former Federal Reserve Chairman Alan Greenspan.

"What I should do is make them into a dart board," says Charles Gradante, who with his wife, Lee Hennessee, runs the Fifth Avenue firm that advises investors in hedge funds. "All I see when I look at these
paintings are two market crashes, a bear market, and the current
economic crisis."

The pictures stay on the wall because of Ms. Hennessee, who remains loyal to the paintings and to the man they portray.

"Wonderful," she says, surveying one canvas. Ms. Hennessee paid $2,500 for the portrait by artist Erin Crowe. She believes the works could grow in value.

The paintings at the center of this husband-and-wife disagreement are artifacts of a bygone era: a time when many Americans thought central bankers were cool, and Mr. Greenspan was the coolest, or
perhaps hottest, of them all.

In the years before the 2008 financial crisis, Wall Street and Mr. Greenspan's reputation boomed in tandem, and an obscure young artist, Ms. Crowe, gained notice for her distinctive oil portraits of the Fed
chairman, now 83 years old. Working from photographs she found online
and in newspapers and magazines, Ms. Crowe produced colorful, whimsical
canvasses that highlighted Mr. Greenspan's wrinkled forehead, pursed
lips, droopy ears, hand gestures and oversize glasses.

A gallery in the Hamptons that exhibited her paintings in the summer of 2005 sold every one within a couple of days, recalls Sally Breen, who organized the show with Rebecca Cooper. She had a second Greenspan
show in downtown Manhattan. Ms. Crowe says she produced upwards of 50
canvasses of Mr. Greenspan. All were snapped up, some for as much as
$5,000 to $10,000, she says.

As her popularity grew, Ms. Crowe flew business class to Hong Kong, where she painted portraits of leading financial figures, including Hong Kong's chief executive and the head of its Monetary Authority. She
realized that she'd found her niche: painting financial gurus. The
future looked dazzling.

She painted one of the portraits on live television when Mr. Greenspan retired. It fetched $150,400 for charity in an online auction.

Now, the man who bought that painting, Tampa Bay-area businessman Matthew Schirmer, says he keeps it under his bed.

Mr. Schirmer says he had high hopes for the painting when he bought it in 2006 with his brother, Nathan. The money they spent went to a worthy cause, autism research. But Mr. Schirmer says he was hoping to
raise even more money for a favorite charity, Autism Speaks.

"We thought, let us ride this wave," he recalls. Mr. Schirmer paid to have 100 high-quality prints made of the painting. He flew Ms. Crowe to Florida to sign them. Her painting was placed on an easel in the
lobby of a Tampa-area bank Mr. Schirmer helped found. Mr. Schirmer
anticipated holding charity fund-raisers with the Greenspan painting as
a draw.

"There was no interest," he says. To this day, he hasn't sold any prints, he says, "not a single one." The original painting could still recover some value, he says. "I hate to tell you, but we are kind of
waiting for him to pass on."

Mr. Greenspan's office said the former Fed chief "regrets he won't have the time to comment."

Brian McAnaney, a lawyer in Stamford, Conn., bought an early Greenspan painting by Ms. Crowe at a charity auction way back for $300. A friend of the artist's family, he hung the painting in his office,
where it remained until he retired. Now he has it hidden away in a
closet in his summer house.

"It is a little hard to find a place for Mr. Greenspan in my homes," Mr. McAnaney says. "He is still there, but in a closet, because it is difficult to find a place for him in a family setting."

As for his summer home, located in Kiawah Island, S.C., he rents it out and fears the image of the controversial former Fed chief could "offend" tenants. Mr. Greenspan, he deadpans, "is not on everybody's
A-list."

How valuable are these portraits? "I doubt these Greenspan paintings could be resold for what people paid for them because they are indicative of the times," Mr. McAnaney says. "They were painted in a
bubble economy, and Erin's paintings were bubbles."

In Washington, Kevin Dolan, a former senior vice president of Merrill Lynch, bought his painting for $3,000. He decided to donate it to a charity auction that took place on the firm's trading floor in
December 2006. It went for nearly double the price, he recalls.

He doesn't believe that would happen now, saying he is relieved that he donated his painting to charity when Mr. Greenspan "was still a god."

Dallas hedge-fund manager David Norcom still has his Greenspan, which he purchased for $3,000 when the Fed chairman's reputation was sterling. "There is not one person who comes to my office that doesn't
talk about it," says Mr. Norcom. "When Greenspan was more admired,
people walked in, looked at him and made positive comments about him,"
says Mr. Norcom. These days, the comments are more acerbic.

"It is a conversation starter," says Mr. Norcom. People say: "Man, everyone thought he was hot, but he turned out to be a dog."

Some who shared in the pre-crash exuberance for Greenspans say they don't see a reason to sell now.

"Alan Greenspan at one time was a hero to most of us, and now he is being called a villain," says Lou Guida, of Jupiter, Fla., who bought several Greenspan paintings for about $2,500 to $8,000 each. "Who knows
what history will say about Alan Greenspan?" Personally, he doesn't see
Mr. Greenspan as a villain, he adds.

Ms. Crowe, now married with a baby and living in London, says she is taking the change in her fortunes in stride.

"I rode those paintings as far as you can imagine, so how can I complain?" she says.

Ms. Crowe hasn't abandoned her niche in the art world, and has now turned her attention to the current Federal Reserve chief, Ben Bernanke.

"It is a fresh face, it didn't have so many wrinkles, it felt baby-like," she says. She hopes to put together a Bernanke show.

But the new Fed chairman's market value can't compare with Mr. Greenspan's at his peak. One patron who had paid Ms. Crowe $10,000 for a Greenspan asked her to paint Mr. Bernanke. But he only wanted to pay
her $5,000, she says.

"I thought, 'Yikes,' " Ms. Crowe says. "That is a hefty pay cut."