NHL: 5 most disastrous general manager tenures in NHL history ft. Mike Milbury, Peter Chiarelli and more

Being an NHL general manager is no easy task. Whether scouting prospects for an upcoming draft, making critical trades at the deadline, or picking the right person to lead the players in the dressing room, not everyone is up to the scrutiny of the position.

Naturally, not everyone is cut to be a general manager, with even the legends struggling to save their reputations in specific markets. Although fans love to voice their displeasure about certain bosses, a few are always talked about more than others.

Even though there could be 100 names on this list, today, we want to discuss five general managers who had disastrous tenures with certain clubs, which fans still talk about, even more than a decade later.

5 most disastrous general manager tenures in NHL history

#5. Doug MacLean (Columbus Blue Jackets)

The Columbus Blue Jackets joined the NHL for the 2000-01 season, with Doug MacLean serving as the club's first general manager. Additionally, the team employed Dave King as the first head coach. The duo built the Blue Jackets through the Expansion Draft but didn't produce a winning season together.

During the first four years, Columbus compiled a league-worst 104-173-33-18 record, with only eight of their first 22 draft picks ever making it into the league. Luckily, MacLean found a franchise star in Rick Nash at the 2002 draft. However, the Blue Jackets never came close to qualifying for the playoffs during his seven seasons in Ohio.

Overall, MacLean has the sixth worst points percentage by a general manager who ran a club for at least 400 games. Since being relieved of his duties in 2007, he hasn't landed another job in the NHL outside of providing commentary on TV.

#4. Glen Sather (New York Rangers)

Glen Sather was the man who led the high-flying Edmonton Oilers through their dynasty in the 1980s, winning five Stanley Cups in seven seasons. His legacy allowed him to become general manager of the New York Rangers in 2000, where he still serves as a senior advisor in 2023-24.

Glen Sather at the 2014 NHL Stanley Cup Final

After running the Oilers as general manager from 1989 to 2000, he jumped to the Big Apple a season after Wayne Gretzky retired. However, he brought back franchise icon Mark Messier in his first season, who left to play in Vancouver. Despite all the good things he did, like drafting Henrik Lundqvist, the team didn't accomplish anything during his time as general manager, which ended in 2015.

Before the salary cap era started in 2005-06, Sather and the Rangers overspent on veteran players in hopes of winning another Stanley Cup. However, the all-star lineups never made it out of the third round of the playoffs. During his tenure, the team went 556-431-25-101 with just 10 playoff series wins

#3. Ron Hextall (Pittsburgh Penguins)

Ron Hextall's best days as an NHL goalie came when he patrolled the crease with the Pittsburgh Penguins cross-state rivals, the Philadelphia Flyers. After a solid 13-year goalie, winning the Vezina and Conn Smythe Trophies, he got into management, winning two Stanley Cups as an assistant general manager with the Los Angeles Kings.

Eventually, Hextall returned to the Flyers to serve as general manager before landing with the Penguins in 2020-21. Considering the franchise was only three removed from being champions, the club's current state rests on Hextall's poor decisions to get older and not younger.

Whether bringing in overpriced veterans who underperform or signing players to deals pitting the team in salary cap trouble, the Penguins may not qualify for the playoffs this year and owe that to Hextall, who was fired in the spring of 2023.

#2. Peter Chiarelli (Edmonton Oilers)

Peter Chiarelli won the Stanley Cup with the Boston Bruins in 2011, working with the Original Six team from 2006 to 2015. Although once they let him go, he wasn't unemployed long because the Oilers hired him before the 2015 Entry Draft when the franchise picked generational talent Connor McDavid.

Peter Chiarelli, former NHL general manager

As the worst team in the NHL the year prior, it would appear that Chiarelli had his job cut out for him, but it turns out he didn't and led the Oilers deeper into the abyss. By the time he came to town, the lineup had featured Taylor Hall, Ryan Nugent-Hopkins and Nail Yakupov, all former first-overall picks.

However, by the time Chiarelli left in 2019, only Nugent-Hopkins and McDavid remained, and the Oilers qualified for the playoffs on just one occasion. Despite some questionable trades, nothing will compare to the mess he put the team in when he signed unproven and unreliable netminder Mikko Koskinen to a highly costly multi-year contract just hours before he was fired.

#1. Mike Milbury (New York Islanders)

Mike Milbury has one of the wildest legacies in NHL history. Not only is he remembered for fighting with a fan in Madison Square Garden in 1979, but he also recently stepped away from his commentary job with NBC for his on-air comments about players during the NHL bubble playoffs in 2020.

However, Milbury's claim to fame will be that he was one of the worst general managers ever when he ran the New York Islanders from 1995 to 2006. Unfortunately, during his time, the franchise only made the playoffs three times: in 2002, 2003, and 2004.

As the last team to win four consecutive Stanley Cup titles in the early 1980s, two decades later, the once proud organization was a laughing stock at the time.

Milbury traded away young players, Zdeno Chara, a future Hall of Famer and Roberto Luongo, a member of the 2022 Hall of Fame class, for almost nothing while signing Alexei Yashin to one of the wealthiest deals in history, only for the forward to underperform for his entire stay with the team.

During Milbury's tenure, the Islanders had a .438 win percentage with a 294-392-86-20 record.