Ottawa Senators 15 Worst Contracts (2005-2022)

This was originally published in my 2020 book The Definitive Guide to Salary Mismanagement, and has now been updated with new contracts. I will continue to update each team’s list every summer going forward. The rule is that only active contracts can move up or down. Expired deals cannot pass each other. Next summer it may even be expanded to top 20. The book is still available on Amazon, though some of the stats on active contracts are now out of date. You may yet find it interesting because there were detailed stat graphics that you won't find here.

My latest book The Hockey Economist’s Betting Prospectus is now available. It's a comprehensive commentary on the last 3 years of hockey betting, broken down by team, by category, by strategy, by season. There is plenty of useful information for bettors of all skill levels. It covers pre-pandemic, peak-pandemic, post-pandemic. What worked, what failed. Lessons learned, market trends, team-by-team analysis. What impact did the pandemic have on hockey betting? The market differences between these 3 seasons are discussed at length, and there's a lot to talk about. To read more, visit the Amazon store.

If you’d like to browse my other best/worst contract lists, click here. Enjoy! 

Please note: The formatting on the graphics got scrambled being copied from Excel into Google Blogger. It's among the reasons my blog is looking for a new home.

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The Ottawa Senators don’t take a lot of big swings on the free agent market, which is mostly a function of their tight budget as a small market franchise, often prohibiting them from breaking the bank in July. They are just as prone as anyone else to making mistakes, but those tend to happen on smaller bets. They don’t sit at the high stakes table.
 
Another reason that you won’t see too many career-destroying transactions on the Sens list is because they spent nearly a decade under the supervision of Bryan Murray, who was generally known to have a great eye for talent, especially at the draft table. The Senators have gained a reputation for being among the best teams at drafting and developing talent, ensuring that there is always a strong pipeline to replace what they lose in free agency.
 
Pierre Dorion made some mistakes early in his tenure trying to pry open the Erik Karlsson window, but once that train left the station, the rebuilding process has been effective. Spending was tightened considerably once the floundering had commenced.
 
 
1. Bobby Ryan

Signed By:	Bryan Murray		Position:	F
Date:	2014-10-01		Age July 1st:	28
Term:	7 years		Playoff GP:	19
Total Money:	$50.8M		Playoff PTS:	15
Cap Hit:	$7.3M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	54.1	307	164	609
Per 82 GP	7.7	82	44	163	16.0

"I promise you we’ll give it everything we have night in and night out to uphold our end of the contract."

– Bobby Ryan

Bryan Murray had seen one season of Bobby Ryan in Ottawa (70 GP, 48 PTS) before signing the winger to this early extension. That stat line warranted maybe a $5M salary (adjusted for cap inflation), but Murray was forced to overpay to entice Bobby to pass up an opportunity at unrestricted free agency. The team had paid a heavy price to acquire him (Silfverberg and a 1st round pick) and it would have been embarrassing if they lost him to unrestricted free agency 2 years later.
 
Bobby had some big moments in the 2017 playoffs, but that’s not worth $7.25M AAV…not even close. Bobby won the title of the worst contract in the whole NHL for 2017. He would average 44 PTS per 82 GP over 5 seasons before being bought out, signing a 1-year deal with the Red Wings shortly thereafter.
 
 
2. Dany Heatley
 

Signed By:	Bryan Murray		Position:	F
Date:	2007-10-03		Age July 1st:	27
Term:	6 years		Playoff GP:	43
Total Money:	$45M		Playoff PTS:	28
Cap Hit:	$7.5M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	61.1	438	320	1186
Per 82 GP	10.2	82	60	222	19.2

“I've said before, I love Ottawa, I love the fans, it's a great organization. So I'm just thrilled to be here for six years."

– Dany Heatley

Dany Heatley decided to bypass an opportunity to reach unrestricted free agency at age 27 by agreeing to this extension and making a long-term promise to stay in Ottawa. He loved Ottawa so much that he negotiated a full no movement clause so the team wouldn’t be able to trade him.
 
After one season, Dany changed his mind and demanded a trade out of town (then later vetoed a deal with Edmonton. The Oilers dodged a bullet). Dany was eventually sent to San Jose for Milan Michalek and a 2nd round pick. Heatley had a good first season in San Jose, but saw his production drop the following year, prompting another trade to the Minnesota Wild for Martin Havlat. That’s where things got ugly, hitting the wall at age 30, spiralling all the way down to 28 PTS in 72 GP in the final year.
 
 
3. Colin White
 

Signed By:	Pierre Dorion		Position:	F
Date:	2019-08-21		Age July 1st:	22
Term:	6 years		Playoff GP:	0
Total Money:	$28.5M		Playoff PTS:	0
Cap Hit:	$4.8M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	28.7	130	51	199
Per 82 GP	4.8	82	32	126	15.3

“Colin plays the 200-foot game that is so coveted in today’s NHL. He can skate, play on both special teams and is a character player and leader who loves hockey and this city. While he is coming off a season where he finished among rookie leaders in many categories, we also know he is just scratching the surface of his potential in this league.”

– Pierre Dorion

Colin White hit peak production in the final year of his entry level contract when he scored 41 PTS in 71 GP. That stat line prorated over 82 GP should have been worth approximately $3.8M. Surely that $1M premium he received was based on the expectation that his ceiling had not yet been reached. Unfortunately he battled injures and only produced 32 PTS per 82 GP, which is worth less than half his actual salary.
 
It reached such a low point that the Senators bought out the final three years. White signed with Florida next, and made an immediate impact with his new team. So it’s entirely possible this was only bad because he wasn’t healthy, which may not be his fault.
 
 
4. Milan Michalek
 

Signed By:	Bryan Murray		Position:	F
Date:	2014-07-01		Age July 1st:	29
Term:	3 years		Playoff GP:	6
Total Money:	$12M		Playoff PTS:	1
Cap Hit:	$4M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	13.9	116	52	200
Per 82 GP	4.6	82	37	141	16.2

“Michalek had a deal at much more money and two years longer than he took in Ottawa.”

– Bryan Murray

Milan Michalek had been a decent point producer over his first 4 seasons in Ottawa (scoring at a 50-point pace) after coming north in the Dany Heatley trade. The Czech winger became an unrestricted free agent at age 29 after scoring 39 PTS in 82 GP, listened to offers from around the NHL, then decided to return to Ottawa.
 
By year two, this investment had broken completely bad, so the Senators dumped him on Toronto as part of the Dion Phaneuf trade. By the final year, Milan played more games for the Marlies than Leafs and was among the highest paid AHLers, which is never an honorable distinction. He has not played professional hockey since.
 
 
5. Jared Cowen
 

Signed By:	Bryan Murray		Position:	D
Date:	2013-09-14		Age July 1st:	22
Term:	4 years		Playoff GP:	0
Total Money:	$12.4M		Playoff PTS:	0
Cap Hit:	$3.1M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	14.8	159	28	138
Per 82 GP	3.7	82	14	71	18.9

“He’s kind of a poster boy of what we want here. He works extremely hard, he’s low maintenance, he plays hard, he competes, we love him as a player.”

– Tim Murray

Jared Cowen was a promising young prospect before a serious knee injury cost him almost a full season in 2012/13. When Murray signed the defenseman to this four-year extension, he was gambling that Cowen would resume his previous career trajectory, but was mistaken. Instead that trajectory turned in the wrong direction, sliding south into a tailspin.
 
Cowen was eventually dumped on Toronto as part of the Dion Phaneuf trade. The Leafs sent him home for the rest of the season to await a buyout. Cowen has not played professional hockey since. He did file a grievance claiming he was ineligible to be bought out due to injury, but lost his case.
 
 
6. Colin Greening
 

Signed By:	Bryan Murray		Position:	F
Date:	2013-09-09		Age July 1st:	28
Term:	3 years		Playoff GP:	0
Total Money:	$8M		Playoff PTS:	0
Cap Hit:	$2.7M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	9.2	57	16	97
Per 82 GP	3.1	82	23	140	12.1

“I think both parties realized they wanted to get it done before the season started”

– Colin Greening

Colin Greening inked a 3-year extension following the lockout shortened 2013 season where he scored at a 33-point pace. He had peaked at 17 goals, 37 PTS, and 189 hits in 2012. There can be a risk extending a player early, because if he starts to suddenly suck, you’re locked in. This strategy can lead to big bargains with younger players before they break-out, but at age 27, it’s probably only going to get worse going forward.
 
Greening produced near replacement level in what should have been his free agent season, and would have been worth considerably less money had they waited. This contract started to suck almost immediately, and produced more AHL games than NHL for Greening. He was among the boatload of mistakes sent to Toronto in exchange for Dion Phaneuf.
 
 
7. Peter Schaefer
 

Signed By:	John Muckler		Position:	F
Date:	2006-07-28		Age July 1st:	28
Term:	4 years		Playoff GP:	27
Total Money:	$8.4M		Playoff PTS:	10
Cap Hit:	$2.1M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	13.5	140	72	223
Per 82 GP	3.4	82	42	131	15.9

"If you go through all the guys in the league, some have nice seasons. Others have bad slumps and bad years. You just try and get through it. You're not going to have great years every year.”

– Peter Schaeffer

Peter Schaefer had developed a reputation as an effective 2-way winger who could contribute offensively while playing a key defensive role. Coming out of the 2005 lockout, Schaefer set a new career high by scoring 20 goals and 50 PTS. CBA provisions meant that the 28-year-old was a restricted free agent at the expiration of his previous deal. John Muckler avoided arbitration by securing Peter’s signature on a 4-year treaty.
 
Year one was a success, with Schaefer scoring 46 PTS playing top six minutes. Then 5 days after his 30th birthday, the Senators traded him to Boston for Shean Donovan. That’s where this venture turned rancid. He spent the entire third year in the AHL before the Bruins bought out the remainder. Peter played 16 more games for Vancouver before departing for Germany.
 
 
8. Matt Murray
 

Signed By:	Pierre Dorion		Position:	G
Date:	2020-10-09		Age July 1st:	26
Term:	4 years		Playoff Wins:	0
Total Money:	$25M		Playoff SV%:	0.000
Cap Hit:	$6.25M		Stanley Cups:	0

 

	Avg Adj Cap Hit	GP	W	GAA	SV%
Total	6.3	47	15	3.23	0.899

"They think that he has addressed some structural flaws that he has had in his game, in terms of moving side to side, that they think make him a better goaltender now."

– Elliotte Friedman

Matt Murray’s last season in Pittsburgh was anything but impressive, playing 38 games with an .899 SV%. He might have been a 2-time Stanley Cup champion, but he had fallen far from his peak performance by the time Pittsburgh was done with him. The Sens traded a prospect and 2nd round pick to acquire Murray, who had 1 year left of team control before he would become an unrestricted free ageny. My prediction for his new contract that summer was 1-year $3.8M, and it turned out to be one of my biggest misses.
 
The Senators paid him like that bad season was just a fluke, but turns out he just was not the same player anymore. His first season in Ottawa was a disaster, winning just 10 games with a 3.38 GAA and .893 SV%. Eventually they traded 3rd and 7th round draft picks to convince Toronto to take Murray off their hands. Kyle Dubas took a lot of criticism for the move.
 
 
9. Ray Emery
 

Signed By:	Bryan Murray		Position:	G
Date:	2007-07-24		Age July 1st:	24
Term:	3 years		Playoff Wins:	0
Total Money:	$9.5M		Playoff SV%:	0.000
Cap Hit:	$3.2M		Stanley Cups:	0

 

	Avg Adj Cap Hit	GP	W	GAA	SV%
Total	4.8	31	12	3.13	0.890

"I like the fact we have three years with him. He's young, we believe he's getting better and we'll certainly know that at the end of this contract."

– Bryan Murray

Ray Emery had an incredible season in 2006/07 at a bargain price with a .918 SV% over 58 GP, helping Ottawa advance to the Stanley Cup final (his SV% dropped to .907 in the playoffs). The Senators gave him a 3-year extension at a high salary that would walk Razor on the fast track to unrestricted free agency.
 
Emery’s magic vanished a few months later, as Ray followed up that finals appearance with an abysmal 3.13 GAA and .890 SV%, earning himself a buyout. That fast track to UFA happened far faster than planned. Ray’s desire to play for the highest bidder landed him in Russia for $2M. Emery played well despite an altercation with a trainer and returned to the NHL in the summer of 2009, though his peak earning power was decidedly behind him.
 
 
10. Alexandre Burrows
 

Signed By:	Pierre Dorion		Position:	F
Date:	2017-02-27		Age July 1st:	36
Term:	2 years		Playoff GP:	0
Total Money:	$5M		Playoff PTS:	0
Cap Hit:	$2.5M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	5.3	71	14	90
Per 82 GP	2.7	82	16	104	11.7

"We had to do something like this. We just felt it was time to add another piece, and in Alex Burrows, I can tell you, we're ecstatic to have added that piece."

– Pierre Dorion

Alex Burrows proved to be a decent rental for the Senators after being acquired from the Canucks, helping the team make a deep run in the playoffs that was worth the prospect they traded. Where they messed up was giving this 2-year extension to a 35-year-old player shortly after the trade.
 
It lasted one season, producing 14 PTS in 71 GP mostly on the 4th line, leading to a buyout. It would have been interesting to see what Burrows could’ve made on the open market, but alas we’ll never know. It’s unlikely that anyone would have given him the 2nd year as a 35+ year old player.
 
 
11. Andrew Hammond
 

Signed By:	Bryan Murray		Position:	G
Date:	2015-05-20		Age July 1st:	27
Term:	3 years		Playoff Wins:	1
Total Money:	$4.1M		Playoff SV%:	0.933
Cap Hit:	$1.4M		Stanley Cups:	0

 

	Avg Adj Cap Hit	GP	W	GAA	SV%
Total	1.5	31	7	2.81	0.907

"The great thing about sports and hockey in particular is anything can happen"

– Andrew Hammond

Andrew Hammond was the original Jordan Binnington, minus the playoff success. Probably nobody in Ottawa thought this 3-year extension was a bad idea after the Hamburgler put up a sensational hot streak to carry the Senators into the playoffs. The cost was not prohibitively expensive, but was still not a price you want to be paying to a minor league goaltender.
 
Hammond wasn’t terrible in year one, but he was supplanted by Craig Anderson, who started 60 games. By year two the crease got even more crowded, as he displaced as backup by Mike Condon, then required hip surgery in February, ending his season. By year three he was thrown into the Matt Duchene trade as a salary dump, and played most of the season in the AHL.
 
 
12. Martin Gerber
 

Signed By:	John Muckler		Position:	G
Date:	2006-07-01		Age July 1st:	31
Term:	3 years		Playoff Wins:	0
Total Money:	$11.1M		Playoff SV%:	0.912
Cap Hit:	$3.7M		Stanley Cups:	0

 

	Avg Adj Cap Hit	GP	W	GAA	SV%
Total	6.1	112	55	2.81	0.907

“He’s what you want from a goalie, just a chance to win it”

– Shean Donovan

The Senators were a team on the verge of a breakout who needed to solidify their net, so they went out and got the #1 goalie from the Stanley Cup champion. Unfortunately, they may have started their summer vacations too early and didn’t notice that Gerber was terrible in the playoffs and supplanted by Cam Ward. Gerber inked an expensive 3-year deal at age 31 with the Senators.
 
The Martin Gerber experiment did not go according to plan in Ottawa, where he was once again unseated by his younger backup who carried the team through the playoffs. The Swiss gatekeeper played decent in year two, stepping up when Emery came crashing back down to earth. By year three he was sent to the AHL and eventually claimed off waivers by Toronto.
 
 
13. Craig Anderson
 

Signed By:	Pierre Dorion		Position:	G
Date:	2017-09-29		Age July 1st:	37
Term:	2 years		Playoff Wins:	0
Total Money:	$9.5M		Playoff SV%:	0.000
Cap Hit:	$4.75M		Stanley Cups:	0

 

	Avg Adj Cap Hit	GP	W	GAA	SV%
Total	4.9	84	28	3.41	0.902

“Whether it was Bryan Murray or Pierre or Eugene, it’s one of those things where you feel the love and you feel the family and you just feed off of that.”

– Craig Anderson

Craig Anderson had just completed a miraculous season at age 36, posting a .926 SV% over 40 GP and playing a key role advancing the team to within an inch of the Stanley Cup final (with a .922 SV% in the playoffs). Pierre Dorion decided to lock the aging veteran into a 2-year extension the following September.
 
The team would have been so much better off to wait until the end of the season before re-signing their goalie because he suffered a massive collapse in 2018 (along with the rest of the team) posting a 3.32 GAA and .898 SV%, before the new deal had even started. Ouch. The magic of 2017 was never seen again. On the bright side, his bad play helped the Senators Avalanche get a higher draft pick and take Bowen Byram.
 
 
14. Evgenii Dadonov
 

Signed By:	Pierre Dorion		Position:	F
Date:	2020-10-15		Age July 1st:	31
Term:	3 years		Playoff GP:	0
Total Money:	$15M		Playoff PTS:	0
Cap Hit:	$5M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	15.1	133	63	266
Per 82 GP	5.0	82	39	164	15.7

“He's someone who scores legit goals, he can really shoot it, he's smart offensively.”

– Pierre Dorion

Evgenii Dadonov found success in Florida playing with Jonathan Huberdeau and Aleksander Barkov, producing like a $5.4M player in his final season there. He was scooped by Ottawa as an unrestricted free agent, at a fair price relative to his stat line. The problem was, how much of that stat line was a product of playing with two immensely talented forwards? Would he be able to carry that output over to Ottawa?
 
The answer proved to be no, as Dadonov scored just 20 PTS in 55 GP for his one campaign in Ottawa, roughly half the production you’d expect for that pay grade. Ottawa was able to move him to Las Vegas in the summer for a decent return, which turned out to make no sense for the Golden Knights. They found themselves in a cap crunch and tried to trade him to Anaheim, not realizing it was on his no-trade list.


15. David Legwand
 

Signed By:	Bryan Murray		Position:	F
Date:	2014-07-04		Age July 1st:	33
Term:	2 years		Playoff GP:	3
Total Money:	$6M		Playoff PTS:	0
Cap Hit:	$3M		Stanley Cups:	0

 

	Adj Cap Hit	GP	PTS	SOG	ATOI
Total	7.1	159	41	152
Per 82 GP	3.5	82	21	78	11.8

“David is a good veteran centre, a guy who skates pretty well and gets up and down the ice. He’s an experienced guy who can fit in either at the top or bottom of the lineup.”

– Bryan Murray

For years, David Legwand was a center who could reliably score 40-50 PTS, scoring 51 at age 33 split between Nashville and Detroit (the Wings traded Calle Jarnkrok and a 2nd round pick procuring Legwand’s help to win one playoff game). After the Red Wings early playoff exit, David tested the UFA market, landing this 2-year deal with Ottawa.
 
The Senators did get him at a cheaper price than a 50-point season should cost, unfortunately, Legwand’s gas tank was close to empty, with his point scoring rate declining by almost half in year one. Despite this disappointing season, Ottawa was able to package Legwand into a trade with Robert Lehner to Buffalo for a 1st round pick (that became Colin White). Bryan Murray kinda fleeced his nephew Tim. I can’t imagine that the Sabres had any interest in Legwand, and instead ate the contract as part of the cost of getting Lehner, who they hoped would be their goalie of the future. Regardless, the Sens got a bad deal off the books. Legwand was below replacement level in year two.