Driven by Ron Pierce, the 3-year-old colt widened out by eight lengths in a mile time in 1:52 4-5. The 56th edition of the Messenger is the third leg of the Pacing Triple Crown.
Roll Joe With sat second for the first half-mile before making his move to the lead and handily defeating his five rivals. Sea Venture, driven by Jason Bartlett, was second, while Sir Ziggy's Z Tam finished third.
"He's as good and as professional as any horse I've driven," said Pierce, who won the race for a third time.
Roll With Joe, the 1-20 wagering favorite, returned $2.10 while increasing his 2011 earnings to $1,649,725.
Roll With Joe, trained by Ed Hart, had six wins, four seconds and two third-place finishes in 14 races this season.
Also Saturday, Rocklamation, driven by Brian Sears, won the $194,890 Lady Maud Pace for 3-year-old fillies.
—Copyright 2011 Associated Press