Senators’ 3 Worst Contracts Ever

The Ottawa Senators have not been known to spend large amounts of cash in free agency. Unfortunately, the franchise has made mistakes when it comes to the re-signing of certain players. In managing contracts, the salary cap is paramount. These contracts handicapped the Senators for years, and some are still having repercussions. These are the worst contracts in team history:

Dis-Honourable Mention: Milan Michalek

Milan Michalek (Photo by sophnsoph9).

Many Senators fans see Milan Michalek as one of the pieces of the Dany Heatley trade. Those same people often overlook how serviceable he was to Ottawa in his first few seasons.

Michalek was two years removed from a 35-goal season, so the $4 million cap hit didn’t seem like an overpayment at the time. However, once he signed his three-year, $12 million extension on July 1, 2014, it all went downhill.

Related: 3 Best Trades in Senators History

The reason his contract isn’t listed as one of the worst in Senators’ history is that the club saw the error of their ways, and sent Michalek to the Toronto Maple Leafs two years into the deal. The Senators got rid of this contract before it became a serious issue, but had to take on the contract of Dion Phaneuf to offset it.

Senators Choose Wade Redden

Wade Redden’s case is an interesting one. As a cornerstone of the Senators’ defensive core for the majority of the late-90s and mid-2000s, he was definitely due for a raise. His very team-friendly deal of just over $3.7 million per year was expiring after the 2005-06 season, and he was going to get his big contract.

Wade Redden Zdeno Chara Jason Spezza Ottawa Senators
In 2006, the Sens had to decide between Wade Redden and Zdeno Chara (Photo by Phillip MacCallum/Getty Images)

The problem was that Zdeno Chara, another big part of the Senators defence, was also due for a new deal. The amount of money to keep both would not be compliant with the salary cap. The Sens had $44 million to build their roster, so both could not get what they deserved. The Senators had to make a choice and on June 30, 2006, they did just that.

The Senators announced that they had re-signed Redden to a two-year, $13 million extension, and allowed Chara to go to free agency. (from ‘Redden’s locked up, but Chara set to walk,’ Globe and Mail, 07/01/2006) Giving Redden this much money obviously didn’t work out for the club, considering how much his play declined over the next two seasons. This contract hurts more when you consider how the Senators had to give up Chara in order to sign this deal.

By 2008, the Sens had enough of the contract, and allowed Redden to leave via free agency, and sign with the New York Rangers. The player likely doesn’t deserve 100 percent of the scrutiny for this deal, but it is still one of the worst in team history.

Craig Anderson Is Paid for His Past

When you sign goalies to contract extensions, it is often a case of high-risk, high-reward. This was the case for Craig Anderson. Even though he is the greatest goaltender in Senators’ history, this latest deal has been very bad for the team. When the contract was signed on Sept. 29, 2017, covering the 2018-19 and 2019-20 seasons, it would be one the team would regret.

Craig Anderson Ottawa Senators
Craig Anderson, former Ottawa Senator (Jess Starr/The Hockey Writers)

Anderson signed a two-year, $9.5 million deal that had a cap hit of $4.75 million. Since he signed that deal, he has put up horrific numbers. In 77 games since the new deal kicked in, he has an awful .902 save percentage and a 3.42 goals-against average. You can argue that these numbers are relative considering the quality of teams that he has had in front of him since 2018, but these numbers are still unacceptable.

Anderson still may be a capable goaltender in the NHL, but the albatross of a contract he holds makes it difficult for the Senators to trade him. With the contract expiring at the end of this season, a 38-year-old goalie whose best years are behind him isn’t an attractive trade piece. Anderson’s contract is an example of why goalies are often overpaid after their prime years. He was, like many other goalies, paid for what he had done in the past.

Bobby Ryan Gets Big Money

When the Senators acquired Bobby Ryan on July 5, 2013, they thought they were getting a replacement for captain Daniel Alfredsson, who left in free agency the same day. They were sorely mistaken. After a decent start with Ottawa, the team re-signed Ryan to a massive seven-year, $50.75 million contract extension on Oct. 2, 2014. This was the largest contract the Sens had ever signed until the Thomas Chabot extension on Sept. 19, 2019.

Bobby Ryan Ottawa Senators
Bobby Ryan was a major disappointment as a Senator (Amy Irvin / The Hockey Writers)

The contract has been bad news since it was signed. In 299 games since his new deal kicked in, Ryan has scored only 62 goals and 160 points. Putting aside his issues with injuries, Ryan has been a major disappointment on the ice. When he arrived from the Ducks, he was expected to be a first-line player. He has never lived up to that pressure. Since his arrival in Ottawa, he has only put up 20 goals in a season twice. This comes after scoring at least 30 goals four years in a row as a Duck.

Considering his cap hit of $7.25 million, this is unacceptable. In recent years, it does appear that Ryan had some issues outside of the rink, and I wish him the best in dealing with his problems. (from ‘SNAPSHOTS: The Senators support Bobby Ryan as he enters player assistance program,’ Ottawa Sun, 11/21/2019) With that, this contract is easily the worst in Senators’ history.

The Impact on Sens Past

Overall, the Sens major contract issues have been very recent. Luckily, the team has not had any horrific contracts aside from Ryan. They have avoided them by trading away players before they desire large deals. Whether or not the Senators will choose to overpay in free agency once they begin their spending to the cap philosophy in 2021, remains to be seen.


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