Kessel is a product of the USA Hockey National Team Development Program as an identified elite player under the age of 18. He finished his amateur career playing collegiate hockey in the NCAA for the University of Minnesota in the Western Collegiate Hockey Association (WCHA) conference. He was then selected fifth overall in the 2006 NHL Entry Draft by the Boston Bruins. After his rookie season, 2006–07, he was awarded the Bill Masterton Memorial Trophy for overcoming testicular cancer while continuing his professional career. In 2009, Kessel was traded from Boston to the Toronto Maple Leafs where he spent six seasons before being dealt to the Pittsburgh Penguins in 2015. Kessel won his first and second Stanley Cup championships with the Pittsburgh Penguins in back to back seasons with wins over the San Jose Sharks and the Nashville Predators, respectively. Kessel is known as a natural goal scorer and for his iron man streak – he is one of three players in the NHL with an active streak (as of October 2019) of over 500 consecutive games.