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Galen Rupp, Jordan Hasay chase more history at Chicago Marathon

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during the Men’s Marathon on Day 16 of the Rio 2016 Olympic Games at Sambodromo on August 21, 2016 in Rio de Janeiro, Brazil.

Quinn Rooney

Galen Rupp and Jordan Hasay look to end the longest U.S. victory drought in Chicago Marathon history, live on NBCSN and NBC Sports Gold on Sunday at 8 a.m. ET.

It’s been 12 years since an American runner won in the Windy City -- Deena Kastor in 2005. The longest gap before that was six years at a race held annually since 1977.

Rupp and Hasay, both coached by three-time New York City Marathon champion Alberto Salazar, already put a stamp on U.S. road racing this year.

Rupp was second and Hasay third at the Boston Marathon on April 17. It marked the best U.S. combined male and female finishes at the world’s oldest annual 26.2-mile race since 1985. (The U.S. hasn’t put male and female runners in the top three in Chicago in the same year since 1996.)

Now, both Oregon runners say they’re in the best form of their short marathon careers heading into Chicago.

Rupp goes into his fourth attempt feeling like a healthy and prepared marathoner for the first time.

The 31-year-old ran his first two marathons in 2016 (winning Olympic Trials, bronze at the Rio Games) while splitting time training for shorter races on the track. For Boston, Rupp was severely limited by plantar fasciitis in the lead up. So much so that he didn’t think he would toe the Hopkinton start line as recently as two weeks before the event.

Salazar told Rupp in Boston that it was one of the mentally toughest races he had ever run.

Still, Rupp has not yet been tested in a fast race. His best 26.2-mile time is 2:09:58 with the caveat that his three marathons thus far have been in difficult conditions. Chicago is a pancake-flat course, but with no pacers.

“I’m hoping that it is a quicker race. I would love for it to be a 2:05 or 2:06 race,” Rupp said by phone Thursday. “I wanted to get in a marathon where I thought it was conducive to running fast. I’m not sure right now I’d be ready to compete in like a Berlin, where it’s a 2:03 race, or a London that’s, like, 2:03, 2:04, given that the only ones I’ve done have all been around 2:10. Even though I felt pretty comfortable for most of the races in there until it really started picking up, you can’t just expect to make those huge jumps from, all of a sudden, running 2:10 to 2:03.”

Rupp, though, refused to speculate how fast he could cover 26.2 miles, if the conditions were ideal.

“I never really like to put a whole lot of limits on what I can do,” he said. “When you start putting certain times, whether you believe it or not, it still puts a limit on what you can do.”

The competition includes world-record holder Dennis Kimetto of Kenya, Olympic silver medalist Feyisa Lilisa of Ethiopia and Stanley Biwott, a New York City Marathon winner. All have run sub-2:05. But Rupp could beat all of them.

Kimetto, who won Berlin in 2:02:57 in 2014, has finished just one marathon in the last 2 1/2 years -- in an unimpressive 2:11:44.

Lilisa, though he pulled away from Rupp in Rio, went 2:15:57 and 2:14:12 at his two most recent marathons.

Biwott dropped out of the Rio Olympic marathon and New York City in 2016 and withdrew before the London Marathon in April with a hamstring injury.

More reliable is defending champion Abel Kirui of Kenya, a 35-year-old with a slower personal best than the younger men in the aforementioned trio. But Kirui is versatile, having taken world titles at two different venues, an Olympic silver medal in 2012 and runners-up in Berlin and London.

Hasay’s competition is thinner but stronger -- Ethiopian Tirunesh Dibaba and Kenyan Florence Kiplagat.

Dibaba, 32, won six Olympic 5000m and 10,000m medals from 2004 through 2012. She has raced two marathons -- placing third in London in 2014 and second there this year -- and is already the third-fastest woman ever at the distance. If she can again get close to that 2:17:56, she’ll be running alone the final miles.

Kiplagat, 30, is trying to become the first runner to win three straight Chicago Marathons. Her winning time last year -- 2:21:32 -- is 88 seconds faster than Hasay’s debut in Boston.

“If I run the effort I ran in Boston on a flat course, it should be a PR,” said Hasay, who has trained more with Rupp leading into her second 26.2-miler. “On paper, I’m fitter than that. My long runs have gone tremendously, and my speed is better than it was before Boston.

“I’m less intimidated by the distance. So I think I’ll be a lot more confident in the latter half of the race. I hope to race that last part. In Boston, I got to mile 18, and it was more of a grind rather than a race.”

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