Having earned himself a place in the American team for the 2009 World Championships in Athletics, Rupp announced he was turning pro, and that Michael Johnson would be his agent. At the World Champsionships, Rupp placed 8th, where he was one of only two non-Africans in the top twelve alongside Dathan Ritzenhein.
He then qualified for and competed at the 2010 IAAF World Indoor Championships. He set a personal best of 7:42.40 for the 3000 m, taking fifth place in the final as a result.
Rupp knocked over twenty seconds off his previous 10,000 m best with a run of 27:10.74 in Palo Alto at the Payton Jordan Invitational in Stanford. Coming into that race, the American 10,000 meter record was 27:13.98 by Meb Keflezighi, and though Rupp's time was over three seconds faster than that, he was beaten to the punch by Chris Solinsky who won the race with a new American record of 26:59.60. Two months later Rupp went on to retain his national title in the 10k with a win at the 2010 USA Outdoor Track and Field Championships. Rupp competed on the 2010 IAAF Diamond League circuit and made a series of improvements to his personal records. He broke four minutes for the mile run at the Pre Classic, running 3:57.72, set a 3000 m outdoor best of 7:43.24 at the London Grand Prix, and then improved his 5000 m time to 13:07.35 at the season-ending Weltklasse meeting.
Rupp took part in the Great Edinburgh Cross Country in 2011 and came second behind Mo Farah, helping the American team to second place. He then took part in the New York City Half Marathon, his debut at that distance, and finished third in a time of 1:00:30, making him the 3rd fastest American at the half marathon. At the 2011 USA Outdoor Track and Field Championships he once again retained his national title in the 10,000 m, closing the last 800 m in a quick 1:52.59, and came back the next day to finish third in the 5,000 m. Later in July he improved his personal best to 13:06.86 in the 5000 m at the Diamond League meeting in Birmingham, out sprinting the reigning world cross country champion Imane Merga for second behind winner Mo Farah.
At the 2011 World Championships in Athletics Rupp finished 7th in the 10,000 meters in a seasonal best of 27:26.84. He then doubled back to run the 5,000 meters, and though he was in the lead with Mo Farah with a little more than a lap remaining, he was outkicked and finished in 9th place with a 13:28.64.
Rupp finished his track season with a new American record in the 10,000 meters as he ran 26:48.00 in finishing 3rd behind winner Kenenisa Bekele at the Memorial Van Damme meet on September 16, 2011. this time ranks him as 16th fastest of all-time
Rupp set a new American indoor record in the 2 mile run as he ran 8:09.72 in finishing 1st at the USATF Classic meet on February 11, 2012. In June, Rupp became the fifth American to run under thirteen minutes for 5000 meters by running 12:58.90 at the Prefontaine Classic. He continued on to win the 10,000 meter race in the 2012 United States Olympic Trials with a time of 27:25.33. The run set a new trials record, breaking Meb Keflezighi's 27:36.49 set in 2004, and secured his second trip to the Olympic games.
On June 28, 2012, Rupp broke Steve Prefontaine's last remaining record, the 5000m Olympic Trials record from 1972, running the race in 13:22.67. This was a historic race for Rupp because it was the first time he had beaten Bernard Lagat, current U.S. record holder over 5000m, in his career as he closed with a monumental last lap of 52 seconds.
On August 4, 2012 at the London Olympic Games, Rupp won the silver medal in the 10,000 meters behind Mo Farah, his training partner, with a time of 27:30:90, running his last lap in 53.8 seconds. This was the first time a US male has received a medal in the Olympic 10,000 meters in 48 years, the last medal being Billy Mills's gold in the 1964 Olympics. He was the only athlete in the top 10 not of East African origin. On August 8, 2012, Rupp advanced to the final of the 5000m with a 6th place finish in 13:17.56. On August 10, in the 5000m Olympic final, Rupp placed 7th in 13:45.04.
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