The Most Regretted Trades By The Ottawa Senators

Since joining the NHL as an expansion franchise in 1992, the Ottawa Senators have been involved in many interesting trades. Some of those trades have paid off in spades for the team.

The Alexei Yashin deal with the New York Islanders landed the Senators Zdeno Chara and the second-overall pick in the 2001 Draft, which was ultimately used to select future captain Jason Spezza. That was one of the biggest wins in hockey history (a massive blow for the Islanders).

However, some trades throughout the team’s history have been considered regrettable for many reasons. This may be the return for certain assets, the circumstances surrounding the trade, or perhaps even the performances of players after leaving Canada’s capital. They may not be considered the absolute worst trades in terms of value, but they are all certainly regrettable in their own way.

Demitra For Olsson

Pavol Demitra was always going to be a long shot to make the NHL, being taken in the ninth round (227th overall) of the 1993 Draft, but the Senators gave up on him far too quickly and suffered as a result.

Demitra dominated in the AHL immediately after being drafted, racking up 44 goals and 115 total points across his first two seasons with the Prince Edward Island Senators. During that stretch, he made brief appearances in the NHL with five goals and nine total points in 28 games.

He once again showed he was far too good for the minors, with 28 goals and 81 points in just 48 games in his third season in the AHL, and he even started to show real promise in the NHL with 17 points (seven goals, 10 assists) in 31 games. This should have given the Senators hope that the following year would be a breakout for the Slovakian.

It wasn’t to be, and Demitra was sent to the St. Louis Blues for Swedish defenceman Christer Olsson. Olsson had been an 11th-round draft pick of the Blues in 1993, and had registered 11 points (two goals, nine assists) in 31 NHL games by the time he was acquired by Ottawa.

He played 25 games in the rest of the 1996-97 season and never played in the NHL again. Olsson returned to Sweden in 1997 and played exclusively in Europe until his retirement in 2005.

Demitra, meanwhile, became a star in the NHL. He was nearly a point-per-game player with the Blues, scoring 204 goals and putting up 493 points in 494 games, winning the Lady Byng Trophy in 2000. He then played for the Los Angeles Kings, Minnesota Wild, and Vancouver Canucks before retiring in 2010. He finished his NHL career with 847 games played, 304 goals, 464 assists for 768 total points.

The trade is easily one of the worst deals in franchise history, with such lopsided results from the players involved making it a clearly regrettable deal that the Ottawa Senators would no doubt love to do-over if they had the chance.

Heatley To San Jose

This next trade is regrettable because the Ottawa Senators moved on from a player who had been a star for the team and could have continued contributing effectively longer if they had kept him and deployed him appropriately.

Dany Heatley is known for his back-to-back 50-goal seasons in Ottawa, but when Cory Clouston arrived as head coach, it spelled the end for Heatley in Canada’s capital. He requested a trade after Clouston began to reduce his playing time, removing him from the top powerplay unit.

The request shocked many within the organization, which felt the team was finally turning a corner with Clouston as coach, and seeing Heatley want out was disappointing.

After a 39-goal, 72-point season in 2008-09, the Senators traded Heatley to the San Jose Sharks, along with a 2010 fifth-round pick. In return, the Senators received former Rocket Richard Trophy winner Jonathan Cheechoo, Milan Michalek, and a 2010 second-round pick.

Cheechoo’s numbers declined consistently since his 56-goal season in 2005-06, and he managed just five goals and 14 total points in 61 games with the Senators. He never played in the NHL again after the 2009-10 season.

Michalek had a decent run with the Senators, playing in 412 games with the team. He couldn’t live up to Heatley’s previous production, but still scored 115 goals and had 224 total points before being traded to the Toronto Maple Leafs as part of the Dion Phaneuf trade in 2016.

The 2010 second-rounder was traded away again and eventually landed with the Chicago Blackhawks, who selected goaltender Kent Simpson 58th overall.

It was a disappointing situation to lose Heatley, who could have played another five seasons in the NHL, scoring 112 goals during spells with the Sharks and Minnesota Wild before a scoreless six-game stint with the Anaheim Ducks in 2014-15. Heatley could have continued to play a key role for the Senators, and Clouston was out as head coach just two years later.

If the team had valued Heatley more, giving him more playing time and responsibility, there’s a chance he stuck around, and the team had more success considering the collective value the players received in return.

Talbot For Gustavsson

This trade is especially relevant to the current state of the Ottawa Senators, who have built a solid team that is essentially live-or-die depending on goaltending. Linus Ullmark has yet to reach the same heights as his Vezina-winning season with the Boston Bruins, and the backup situation is a serious question mark for a team looking to progress in the playoffs after back-to-back first-round exits.

Filip Gustavsson was the Senators’ goaltender of the future. The team acquired him from the Pittsburgh Penguins in the multi-asset 2018 Derick Brassard deal. By the end of the 2021-22 season, Gustavsson had shown flashes of his talent and was just 23 years old. However, the Senators took the impatient route and swapped him for veteran Cam Talbot in hopes of shoring up their goaltending.