During the 2003-04 season, Jason Bailey played for the Nepean Raiders in he CJHL. Also during that year, he played for Team Ontario at the 2003 World U-17 Hockey where he earned a gold medal. With Bailey having dual citizenship between Canada and the States, he decided to suit up with the USNTDP during the 2004-05 season. While playing with their U-18 squad, he scored a total of 18 points (7 goals and 11 assists) and racked up a team-high 172 penalty minutes in 47 games played.
3rd round (#63 overall), 2005 by Anaheim.
Bailey also played for the U.S. National U-18 team at the Compuware Four Nations Cup held in Ann Arbor, Michigan, the Five Nations Tournament that took place in Tjorn, Sweden, and the 2005 IIHF World U-18 Championship in Plzen, Czech Republic.
Sep 4, 2009 : Traded to Ottawa Senators from the Anaheim Ducks in exchange for Shawn Weller.
2009-10: Bailey’s first tour within the Senators organization produced 6 goals and an assist in 62 games with Binghamton, to go with 78 Penalty minutes.
A speedy checker who leaves it all out on the ice, Jason Bailey has minimal offensive potential but is at his best when he is making room for his teammates by driving hard to the net and bowling over opposing players. By no means the largest player out there, Bailey's rambunctious style often lends itself to injury, but he has the willingness to play hurt and do whatever it takes to win, making him a leader both on and off the ice.