Jerry Crawford, a top Iowa political kingmaker, watches as his horse, Keen Ice, races at the Fair Grounds Race Course in New Orleans on Feb. 21. (Edmund D. Fountain/for The Washington Post)

Jerry Crawford, Hillary Rodham Clinton’s once and future main man in Iowa, was in his element: sorting through a pile of illegible notes, one eye tracking the latest reports on a mini-TV and another on an iPad stuffed with data. “We’ve Obama’ed it up a little,” he said with a smirk.

Crawford scribbled what looked like hieroglyphics — his wife sometimes calls him “Rain Man” — on a sheet of paper. Then he adjusted his prescription Oakleys and picked up his phone. “So, ready to run?”

Moments later Crawford’s contender emerged, looking like a champion: Eager eyes. Thick skin under a brown coat. Quite literally champing at the bit.*

Keen Ice, his 3-year-old colt.

It’s true: One of the major players in the quadrennial political horse race is an actual racehorse owner, too.

Soon Crawford will apply his Rain Man skills yet again to Clinton and the Iowa caucuses. But today was all about Keen Ice and his mercifully shorter gallop around the New Orleans Fair Grounds track. If Crawford fails to send one horse to the White House, he at least hopes to send another to the Kentucky Derby.

A lawyer with white hair mowed like a golf-course fairway, Crawford is something of a kingmaker back home in Des Moines. He has shepherded every Democratic presidential nominee in the most important caucus state going back to 1980 — every nominee except for one, that is. Crawford, 65, still blames himself for Clinton’s 2008 third-place finish in the Hawkeye State, from which her campaign never really recovered. He vows that 2016 will be his year to make it right for her. “I’m trying to make amends,” he said.

[In Iowa, it’s steaks and high stakes for Hillary Clinton]

The same year Clinton lost, Crawford bought eight horses and started a racing partnership. “The thing about both politics and racing,” Crawford told me, “is that both of them are really about trying to see the future.”

As it happens, the two horses he has already taken to the Kentucky Derby came in third as well. For a man as competitive as Crawford, the next couple of years will be all about changing that story line.

“I’m going to need this horse to at least place for my well-being,” Crawford said.

High up in one of Des Moines’ few towers, Crawford’s law office looks down on the state Capitol like it’s his personal domain. The suite is filled with equine souvenirs, from trophies to framed newspaper articles celebrating the man’s ability to pick winners.

But it was Crawford’s inability to help Clinton win in his home state six years earlier that was still bothering him when I talked to him there during the midterm elections last year.

“Last time we failed in Iowa, and I hold myself responsible,” said Crawford, who has been known to interrupt media interviews to take phone calls about horse-breeding decisions. “I didn’t see it coming. I should have seen it happening and I didn’t.”

Yet, his relationship with the Clintons remained solid. Just days after the stinging loss, Bill Clinton called Crawford while the returns from New Hampshire came in. They spoke for more than an hour. This time around, Crawford has been advising the Ready for Hillary super PAC. He says he will do whatever he can for Clinton.

Crawford wants Clinton to run a more personal campaign, something akin to her first Senate bid, when she spent months traveling around New York and meeting with small groups on a “listening tour.” If there was a big mistake in 2008, he says, it was knocking only on the doors of people they thought would come out to vote. Clinton’s advisers underestimated the anger at the establishment, he said, and when thousands more Democrats showed up to vote, they were caught flat-footed.

[Jerry Crawford on the difference between 2008 and now for Clinton]

“It’s not that we went about it wrong,” Crawford said. “Clinton got more votes than any other candidate in the history of the caucuses. It’s just that [John] Edwards and [Barack] Obama got more.”


Crawford fist-bumps his Donegal Racing partner Keith Mason before a race. (Edmund D. Fountain/for The Washington Post)

Crawford says that his life’s passions are an accident of geography. He grew up on a farm with a grandfather who loved horses, in one of the most important states in presidential politics.

“If I was from anywhere else, nobody would know who I am,” he said. At various times since 1980, Crawford has been the Iowa co-chair, the Midwest co-chair, the Iowa campaign director and the state legal counsel for Democratic candidates. The title isn’t important.

“Last time I was ‘Midwestern chair.’ It means absolutely nothing,” he said. “I’ve been ‘state chair’ of presidential campaigns. I’ve been ‘campaign director.’ I don’t even know what the difference is.”

What he does know is how to pick a winner. Even the ones who came from behind: Sometimes it’s less about a fast start than surging when it matters. In the 2004 race, just weeks before the Iowa caucuses, some people were predicting that Sen. John F. Kerry would come in third and flame out before New Hampshire. But Crawford, who had set Kerry up with an Iowa campaign manager, had some tricks up his sleeve. Kerry often told a story about rescuing a man from the water during a river ambush in Vietnam’s Mekong Delta. Some cynics doubted that the man existed — until January 2004, when Crawford organized a public event with him in Des Moines.

“When he talked about how Kerry saved his life, nobody doubted his service at that moment,” Crawford said.

Crawford is a human Rolodex in a state where connections deliver votes. He’s had a salad named after him in a Des Moines restaurant, helped a state senator battle alcoholism (an AA veteran himself, it will be 25 years April 1 since he last had a drink), owned a local minor league basketball team (before selling it to the Memphis Grizzlies) and won a Tony (as a producer of Broadway’s “A Gentleman’s Guide to Love and Murder”), and is a must-visit for anyone thinking of running for office. Even Republicans seem to like him. David Kochel, the Iowa power player who will run Jeb Bush’s likely presidential campaign, said he “always respected” Crawford’s career.


Crawford confers with jockey James Graham before he mounts Keen Ice for a race. (Edmund D. Fountain/for The Washington Post)

The morning of the big race, Crawford and a half-dozen of his partners — a self-described “degenerate gambler,” a mother and her 15-year-old daughter, the wife of the orthopedic surgeon for the St. Louis Rams, and Crawford’s law partner — tried to shed nervous energy by reminiscing over po-boy sandwiches about lewd thoroughbred names: “Tear the Rubber Off,” “One More Good Yank,” “Is It in Good,” “Shut the Box.”

“You remember the time Paddy O’Prado arrived at the paddock with an erection?” Crawford asked his pals. “The TV commentator said to us, ‘Your horse is the favorite, but we can’t even show him on television.’ ”

It was good for a laugh. But the only real way to relieve the stress at this table was to start gambling. Winning is the only thing.

“Anyone want in on the eight-horse in Gulfstream?” Crawford asked, referring to a race that was about to start in Florida. He told me he spends half an hour examining each race, trying to assess which horses are better than their odds suggest. “I’m not willing to answer questions, just willing to make a bet for you.”

Everyone bet $20 on his recommended horse. Bingo: a $100 payout for each. (Crawford wouldn’t say what he bet or won.)

In 2008, Crawford bought eight horses for $410,000 and started a partnership with a group of friends. The Donegal team — named after a county in his ancestral Ireland — now spends about $2 million to $3 million a year on horses and is made up of about 25 partners.

They are a smaller operation than some titans of the sport. But they have already managed to send two horses — Paddy O’Prado in 2010, Dullahan in 2012 — to third-place finishes in the Kentucky Derby. Unlike most teams, Crawford says, they use a true “moneyball” approach to get bang for their buck. He has an algorithm, which he shares only with his son, that takes into account a young horse’s DNA, X-rays of its joints, a monitoring of its heart, a scoping of its throat and a series of expert opinions on its physique.

They won’t divulge their winnings but maintain that since they started using it, they have made more than they have lost.

“We’re going up against people who spend tens of millions, hundreds of millions, billions of dollars,” Crawford said. “We’re much more grass-roots.”

The hope was that Keen Ice — a horse built like a fullback who starts off slowly but gathers steam as he runs — could be their third entrant in the Derby.

Hillary Clinton has her own history with racing, even if she’d rather forget it.

In 2008, the then-presidential candidate announced that she was betting on a female horse named Eight Belles to win the Kentucky Derby. The filly broke both of her front ankles and had to be euthanized on the track.

Maybe Clinton should have sought Crawford’s advice. Or maybe it wouldn’t have mattered. After I lost $20 on a tip from one of Crawford’s friends, Crawford beckoned me to his workstation to impart some wisdom.

I followed it and lost $40 more.

But all this betting was a sideshow. What Crawford and company had really come for was to see Keen Ice, and now he was being escorted to the paddock. A big, beautiful creature, Ice bucked his head up and down, eager for the race.

“It’s just like the caucuses,” Crawford said.

The bugle played, the horses took their spots at the gate, and they were off. Ice started out behind the pack, but he’s the type of horse who picks up speed as a race goes on. As a younger man, Crawford used to whoop and holler and even run alongside his horses, but now he stood stoically in the bleachers, gazing through mini-binoculars.

As the horses galloped toward the finish line, Ice made his move. Bolting from the back of the pack, he closed in on the top two horses, gaining speed as the other ponies slowed down. But there wasn’t enough track. This race was a mile and a sixteenth, about an eighth of a mile shorter than the Kentucky Derby. Ice came in a shrinking three lengths behind the winner.

Another third-place finish. Crawford’s getting used to those.

“That was tough,” he said, heading over to get the jockey’s explanation.

“He was just getting going; s---, he was only getting going,” the jockey said in his Irish brogue, the dirt of the track flying off his lips. “He did everything right. He just needed one-sixteenth of a mile more to pull ahead.”

Crawford sidled up to a racing reporter. He had his line all figured out.

“That’s the Derby winner right there — we just need to get him in the Derby,” he said. “As my friend Michael Dukakis told me, there are two things you need to be a great president. And one of them is to be president.”

*Note: The following are the bad puns excised from this story: “jockeying for donors”; “long in the tooth”; “back in the saddle”; “critics claim Clinton is more of a show pony than a workhorse”; “does Clinton have the legs for the race?” Also: something about a gift horse; something about riding in on a white horse; something about a photo finish.