Connolly was a gifted stickhandler who was especially strong at orchestrating the power play. He was able to draw opponents out of position with clever delays. He was quick to take advantage, with quick passes to a suddenly open man. He also had an explosive wrist shot and he was able to disguise his release until the last moment.
Connolly was a shifty skater who could make a defender look silly with a quick head fake here or a twist of the stick here. There was no denying his skill level and his on-ice intelligence. Because he did not have a lot of upper body strength he was not always able to to use his skills to his fullest advantages.
His talent was obvious, which is why the New York Islanders drafted Connolly 5th overall in the 1999 NHL draft. Based on talent alone he may have been the number one prospect that year.
After two seasons with the Islanders they would package him and Taylor Pyatt to Buffalo in exchange for Michael Peca.
Connolly, a Syracuse native, played the bulk of his career in Buffalo, often teasing with skill but was more often than not was a frustrating enigma. Connolly was a very fragile player, and missed much time with injuries. The scariest of these injuries were repeated concussions that cost him basically two full NHL seasons. He also suffered hip and back injuries that caused him to miss significant time.
Connolly, who played a final season in Toronto, retired in 2012. In 697 career games he scored 131 goals, 300 assists and 431 points.