Jessiman grew up in Darien, Connecticut, attending Brunswick School in Greenwich.[citation needed] As a youth, he played in the 1998 Quebec International Pee-Wee Hockey Tournament with the New Jersey Devils minor ice hockey team. Jessiman was drafted in the first round, 12th overall, by the New York Rangers in the 2003 NHL Entry Draft.[citation needed]\n', '

After failing to meet the expectations of a first-round draft pick, on October 30, 2008, Jessiman was traded to the Nashville Predators in exchange for future considerations.\n', '

On August 4, 2010, Jessiman signed a one-year contract with the Chicago Blackhawks for the 2010–11 season. After attending the Blackhawks\' training camp, on September 27, 2010, he was waived by the team and assigned to their American Hockey League (AHL) affiliate, the Rockford IceHogs.\n', '

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