Background
Jessiman grew up in Darien, Connecticut, attending Brunswick School in Greenwich.
Jessiman grew up in Darien, Connecticut, attending Brunswick School in Greenwich.
Drafted by the New York Rangers in the first round (12th overall) of the 2003 National Hockey League Entry Draft, Jessiman has previously played in the National Hockey League with the Florida Panthers but has spent the majority of his pro career thus far in the American Hockey League. Jessiman was drafted in the first round, 12th overall, by the New York Rangers in the 2003 National Hockey League Entry Draft. After failing to meet the expectations of a first round draft pick, Jessiman was traded to the Nashville Predators on October 30, 2008, in exchange for future considerations.
On August 4, 2010, Jessiman signed a one-year contract with the Chicago Blackhawks for the ensuing 2010-2011 season.
After attending the Blackhawks training camp, on September 27, 2010, Jessiman was waived by the team and assigned to AHL affiliate, the Rockford IceHogs. Jessiman contributed 5 points in 25 games with the IceHogs before he was traded by the Blackhawks to the Florida Panthers, along with Jack Skille and David Pacan, for Michael Frolik and Alexander Salak on February 9, 2011.
On February 27, 2011, Jessiman made his long awaited National Hockey League debut when the Florida Panthers were defeated by the New Jersey Devils, 2-1. In 43 games with the Monsters, Jessiman matched his AHL career highs of 20 goals before he was signed to a standard player contract for the remainder of the season with the Abbotsford Heat on February 13, 2012.
On July 3, 2012, Jessiman signed a one-year, two-way contract with the Ottawa Senators.
Due to the National Hockey League lockout he was assigned directly to AHL affiliate, the Binghamton Senators. Over the duration of the 2012-2013, Jessiman failed to recapture his previous season production finishing with 10 goals in 68 games for the Senators. On May 23, 2013, Jessiman signed his first contract abroad on a one-year deal with new KHL team Medveščak Zagreb from Croatia.
In the 2013-2014 season, Jessiman was unable to show an offensive touch but found his place using physicality on the third line with Zagreb, for 8 goals and 11 points in 37 games.
A free agent, Jessiman continued his journeyman career, signing a one-year contract with Austrian club, the Vienna Capitals of the EBEL, on July 7, 2014.