Prior to his NHL career, Rolston played for Lake Superior State University (where as a freshman he scored the game-winning goal and earned Most Outstanding Player honors in the National Championship game, which his team won), then the Albany River Rats of the American Hockey League (AHL).

He scored a then career-high 62 points, including nine shorthanded goals in 2001–02 with the Bruins to establish a club record.

Rolston often quarterbacked the Wild's powerplay (a task normally given to a defenseman) due to his booming shot from the point and strong two-way ability.

During the season, he was an on-ice leader and was one of the Wild's top scorers, scoring a new career high of 79 points.

In a similar event during the 2006–07 NHL season, Rolston fired a slapshot on Vancouver Canucks goaltender Roberto Luongo.

[citation needed] On June 29, 2008, Rolston's negotiating rights were traded to the Tampa Bay Lightning in return for a conditional draft pick in 2009 or 2010.

In reaction to the trade, Rolston was quoted by The Star Ledger as saying, "It's been a bit of a rough ride in Jersey, I'm actually happy to go to a place that wants me.

Rolston had been waived by the Devils during the 2010–11 season, and was then entering the final year of the four-year contract he signed in 2008.

[5] After a poor performance on the Islanders where he only scored nine points, Rolston was traded to the Boston Bruins (along with Mike Mottau) in exchange for Yannick Riendeau and Marc Cantin.

The very next day, in a game against the Vancouver Canucks, Rolston scored on a penalty shot, beating goaltender Roberto Luongo with a slapshot.