Mike Milbury's journey in the world of hockey began as a player, where he spent his entire NHL career with the Boston Bruins. Drafted in 1974, Milbury joined the Bruins in the 1975-76 season. Known for his physical style of play, he quickly became a fixture on the team's defense. Over the course of his playing career, Milbury participated in 754 regular-season games, contributing both defensively and offensively with a total of 238 points.

Milbury's playing days were marked by his aggressive approach on the ice, which often led to memorable moments, including his involvement in the infamous 1979 brawl at Madison Square Garden, where he famously entered the stands to confront a fan. This incident, while controversial, highlighted his fiery nature and willingness to stand up for his team.

After retiring as a player in 1987, Milbury transitioned into coaching and management. He began his coaching career with the Bruins, serving as an assistant coach before being promoted to head coach in 1989. Under his leadership, the Bruins reached the Stanley Cup Finals in 1990, though they ultimately fell to the Edmonton Oilers. Milbury's tenure as head coach lasted until 1991, after which he moved into a management role.

In 1995, Milbury took on the role of head coach and general manager for the New York Islanders. His time with the Islanders was marked by a series of bold and often controversial decisions. As general manager, Milbury was known for making numerous trades and roster changes, some of which were heavily criticized by fans and analysts alike. Despite the challenges, he remained with the Islanders organization in various capacities until 2006.

Throughout his career, Milbury was never one to shy away from controversy, whether as a player, coach, or executive. His tenure in the NHL was characterized by a willingness to take risks and make tough decisions, even if they were not always popular. After leaving the Islanders, Milbury transitioned into a broadcasting career, where he continued to share his insights and opinions on the game.

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