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In an unexpected twist, Kessel was traded to the Pittsburgh Penguins, where he became a vital contributor to the team's success. Pairing alongside superstars Sidney Crosby and Evgeni Malkin, Kessel filled in the gaps in playoff pressure, ultimately helping the Penguins secure two consecutive Stanley Cup championships. His ability to perform well under pressure solidified his legacy, allowing him to silence detractors with remarkable performances that included leading the team in scoring during the playoffs.
Notably, after his second championship, Kessel celebrated the victory by posting a humorous photograph of himself eating hot dogs out of the Stanley Cup, putting his trademark sense of humor on display.