[citation needed] 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.

[3] 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.

[4] Jessiman contributed 5 points in 25 games with the IceHogs before he was traded to the Florida Panthers (along with Jack Skille and David Pacan) in exchange for Michael Frolík and Alexander Salák on February 9, 2011.

In 43 games with the Monsters, he 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.

[citation needed] As free agent, on July 7, 2014, Jessiman continued his journeyman career after signing a one-year contract with the Vienna Capitals of the Austrian Hockey League (EBEL).