Three Kings and a $25,000 Pot

Rick Daly found a novel way to finalize the deal—poker

Published in 2009 Texas Rising Stars magazine

By Jim Walsh on March 13, 2009


What would you get if Sergio Leone met Denny Crane?

Meet Rick Daly.

Daly, a young hot-shot attorney with Houston’s Caddell & Chapman, was negotiating a mid-six-figure settlement with one of several defendants in a lawsuit he filed on behalf of a couple who had lost their son in a grain elevator accident. After much negotiation, both sides were $25,000 apart. The defendant instructed the lawyer to offer the last $25,000 up for chance.

“Flip you for it,” said the lawyer.

“Why?” asked Daly.

“My client’s a gambling guy,” the other lawyer said.

Hearing that, Daly replied: “If he’s a gambler, tell him I want to play heads-up poker for it.”

In reality, Daly wasn’t gambling his clients’ settlement money. He and his firm already had decided to make up the $25,000 difference out of its fee. But Daly, a former UCLA tight end who once had pro football aspirations and enjoys the heat of a challenge, didn’t want to give up $25,000 without a fight.

“I wasn’t putting my client’s money on the line,” he says. “I was putting my money on the line.”

And yet, Daly, 38, who has played poker weekly for the past 10 years, wasn’t really worried. He considers himself a strong player. What he didn’t know at the time was that the other lawyer was a pretty fair player himself—actually, better than fair—having done well in a number of poker tournaments and even the World Series of Poker.

After consulting with his client’s president, the lawyer told Daly the president had accepted the offer and designated his general counsel to play.


Growing up in Friendswood, Daly discovered something pretty early. He was a really good football player—and he really enjoyed competing. A pass-catching tight end, he’d made recruiting trips to LSU, Stanford, Purdue and UCLA. He decided early to commit to LSU. Then he took a trip to Los Angeles.

“Of course,” he says, “I went and saw the beach.”

Hello, UCLA.

Five years later, after facing Trojans and Ducks and Sun Devils on the gridiron and attending football mini-camp with the Denver Broncos, Daly decided “it was time to get on with my life, time for me to get on with my legal career.”

Of course, he wanted to be a litigator—the competition, after all. He ended up attending the University of Illinois College of Law because it was the only school to agree to defer his acceptance until after he’d given pro football a try.

Something happened to Daly in law school. He became a top student. No longer burdened by the time football gobbled up in his life, he graduated from Illinois magna cum laude and in the top 10 of his class.

“Your mindset changes, and your focus changes,” Daly says of the intensity he now poured into his legal studies.

For the first 10 years of his legal life, he worked as a litigator for Gardere Wynne Sewell, one of Texas’ largest firms.

“I wanted a firm with a good reputation that would let me into the courtroom at a young age,” Daly says. “That’s rare.”

Daly tried about 30 cases and made partner. But that competitive fire kept gnawing at him, he said. He’d always wanted to be a plaintiff’s attorney.

“I didn’t want to get paid unless I won,” he says.

A little competitive? “Not a little,” says Daly. “A lot.”

“You get the opportunity to hit a home run that you’ll never hit as a defense attorney,” he says.

He’s done well at Caddell. He’s been named one of Houston’s Top Professionals on the Fast Track by H Texas Magazine and has been selected for inclusion in Texas Rising Stars several times. So it’s not hard to figure out how Daly, after all those football games, after all those cases, after all that “friendly” poker, would respond to an offer of a coin flip for $25,000.

Cue the Sergio Leone music.

At 2 p.m. on the appointed day, the men squared off across the poker table. The game: Texas Hold ’em. The setting: A private Dallas club. Each player began with $10,000 in chips.

As the hours ticked by, Daly remembers, “I kept thinking that it was much more difficult than I thought it would be.”

After several hours of playing, each lawyer’s respective chip stacks were even. But the tide began to turn after one hand.

Daly had a king and a queen. The flop—the community cards used by both players—gave both players two more kings and a three. “I had a monster hand,” he says—a hand that most people would be willing to risk their entire stack of chips on.

But the other player, too, seemed to have a strong hand. He raised immediately after Daly bet $400. “He hadn’t really been raising like that,” Daly says. “I decided that on the next card, I would bet $900, no matter what. If he hesitates, I’ve got him. If he doesn’t, he has Ace-King.”

Another card, the $900 bet, and the man immediately raised again. His lack of hesitation led Daly to fold. The man flashed an ace and a king as he raked in the chips.  Daly’s fold saved him from losing the entire match and future winnings. Having discovered his opponent’s strategy—playing very conservatively and only willing to raise when he had such an enormous hand that he couldn’t lose—Daly repeatedly bluffed over the next several hours, making out with 80 percent of the chips, when the game ended so he could catch his flight. So, has Daly added poker to his repertoire for settling legal disputes?

He laughs: “I think that was the first—and last—time.”

Search attorney feature articles

Featured lawyers

Richard D. Daly

Richard D. Daly

Top rated Insurance Coverage lawyer Daly & Black, P.C. Houston, TX

Other featured articles

“Lifetime Detroiter” Saul Green fights every day for his city and its people

Jeff Anderson on law school, legal tactics and his ultimate goal—deposing Pope Benedict XVI

Jill Smith is the hip, sardonic attorney making deals for Lego, Rube Goldberg and Godzilla

View more articles featuring lawyers

Find top lawyers with confidence

The Super Lawyers patented selection process is peer influenced and research driven, selecting the top 5% of attorneys to the Super Lawyers lists each year. We know lawyers and make it easy to connect with them.

Find a lawyer near you