Caleb Paine

Caleb Paine

Caleb has been sailing his entire life and started racing at the age of 7. After finishing high school, Caleb decided to put college on hold so he could pursue his lifelong dream of winning an Olympic gold medal. He bought himself a Finn and began competing full time in 2009. In 2011, he joined the US Sailing Team Sperry Top-Sider and has since been climbing the world ranking in preparation toward his goal.

The most challenging aspect of Caleb’s quest for the gold has been financial resources. It took him 5 years to get a new mast and boat made to his specifications. Over the last few years, with Bill Kreysler’s help and financial assistance from the Foundation, Caleb has had more resources to refine his equipment and spend more time sailing in Rio and other parts of the world, which successfully culminated in a bronze medal in the 2016 Olympics.


3rd 2016 Olympics
1st 2015 Finn North Americans
5th 2015 ISAF Sailing World Cup Hyères
7th 2015 ISAF Sailing World Championship, Santander
3rd 2015 ISAF Sailing World Cup Final Abu Dhabi
1st 2011-12 ISAF Sailing World Cup Series
1st 2013 ISAD Sailing World Cup Miami USA
3rd 2012 ISAF Sailing World Cup Kiel GER
1st 2012 Delta Lloyd Regatta (ISAF Sailing World Cup) Medemblik Holland
2nd 2011 US National Championship, Long Beach, CA


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