When I make best contracts list I prefer rewarding those that produce Stanley Cups. Conversely, I try to avoid championships when making a worst contracts list. If a player gets a ring under that contract while making a contribution in the playoffs, how bad can it be? You’re not getting in a time machine and changing anything. Since Chicago has 3 Stanley Cup victories in the salary cap era, this makes their best and worst lists tricky. There are a whole bunch of Cup winning contracts, and a limited number of big money deals that did not get a ring (thank heavens for Khabibulin and Huet).
Entry level contracts not included.
1- Jonathon Toews, Dec 2 2009, 5 years $31.5M: Signed by Stan Bowman. This contract produced 2 Stanley Cups, a playoff MVP, a Selke trophy, and a regular season stat line of 343 GP, 315 PTS, 946 shots, 4002 face off wins, 16 short handed PTS, and +126 rating. That’s awesome.
2- Duncan Keith, July 13 2006, 4 years $5.9M: Signed by Dale Tallon. This contract won a Stanley Cup and a Norris trophy. The regular season stat line of 323 GP, 176 PTS, 656 shots, and +84 for under $6M is incredible.
3- Patrick Kane, Dec 2 2009, 5 years $31.5M: Signed by Stan Bowman. They got 332 GP, 327 PTS regular season and 2 Stanley Cups. That’s a win no matter how you keep score. Oh yeah and he was playoff MVP for one of those championships.
4- Marian Hossa, July 1 2009, 12 years $63.3M: Signed by Dale Tallon. They won 3 Stanley Cups on this contract. It doesn’t matter what the cap recapture penalty is, you wouldn’t change anything even if you had access to a time machine.
5- Duncan Keith, Dec 3 2009, 13 years $72M: Signed by Stan Bowman. This contract won 2 Stanley Cups and a Norris trophy. This has proven to be a great contract for Chicago.
6- Patrick Sharp, Jan 17 2008, 4 years $15.6M: Signed by Dale Tallon. He won a Stanley Cup with a regular season stat line of 291 GP, 250 PTS, and 1000 shots.
7- Brent Seabrook, Feb 18 2008, 3 years $10.5M: Signed by Dale Tallon. 242 regular season GP, 104 PTS, and a Stanley Cup.
8- Brent Seabrook, Feb 27 2011, 5 years $29M: Signed by Stan Bowman. They won 2 Stanley Cups on this contract. Seabrook could have been the best defenseman on several NHL teams. The Hawks got lucky with two great #1 D-men.
9- Patrick Sharp, Aug 3 2011, 5 years $29.5M: Signed by Stan Bowman. They won 2 Stanley Cups on this contract (where Sharp contributed 15 playoff goals).
10- David Bolland, June 29 2009, 5 years $16.9M: Signed by Dale Tallon. Under this contract the Hawks won 2 Stanley Cups and got 22 playoff PTS in those championship seasons.
WORST (Ranked by total $ spent)
1- Brent Seabrook, Sep 26 2015, 8 years $55M: Signed by Stan Bowman. He was a decent player in season one, but this got ugly by season two. Now he’s 32 years old with 6 years left. Not good.
2- Nikolai Khabibulin, Aug 5 2005, 4 years $27M: Signed by Dale Tallon. Do the Blackhawks get Patrick Kane if they don’t sign Khabibulin? I’m not sure you change anything with the time machine.
3- Cristobal Huet, July 1st 2008, 4 years $22.5M: Signed by Dale Tallon. He finished this contract being loaned to Europe for salary cap circumvention purposes.
4- Martin Havlat, July 7 2006, 3 years $18M: Signed by Dale Tallon. Let’s not forget that the cap was much smaller in 2006. That’s the equivalent of $10M AAV in today’s money. He was reasonably productive under this contract, but that’s still too much for Havlat. It wasn’t until he left Chicago that they won a Cup.
5- Adrian Aucoin, Aug 2 2005, 4 years $16M: Signed by Dale Tallon. With a $39M salary cap this contract is equivalent to $7.4M AAV in 2017 money. For the first two seasons, he had 22 PTS in 92 GP and was -35. Not what you paid for.
6- Steve Montador, June 30 2011, 4 years $11M: Signed by Stan Bowman. RIP. With all due respect to the dead, this was a terrible contract. It’s possible that head injuries contributed to how much he sucked as a Blackhawk. There just aren’t that many bad contracts to choose from.
7- Cam Barker, July 6 2009, 3 years $9.25M: Signed by Dale Tallon. This contract was bought out. The Blackhawks did not win a Cup until they traded this contract to Minnesota. His career took a steep nose dive almost the moment he left Chicago.
8- Martin Lapointe, Aug 4 2005, 3 years $7.8M: Signed by Dale Tallon. That’s like $4.5M AAV in today’s dollars. He had 1 decent season left in the tank but stayed for 3. Ironically enough he was traded away at the end for a 6th round pick that became Ben Smith. That takes us to…
9- Ben Smith, June 27 2014, 2 years $3M: Signed by Stan Bowman. Shipped to San Jose in year 1 before Chicago won another Cup. Smith ended this contract in the AHL. Note that I rank the worst contracts by total dollars spent, so I did not deliberately rank Smith after the guy he was traded for. That was 100% a coincidence and the first time I’ve observed a “worst contract” being traded for a draft pick that became a “worst contract”. There has to be more.
10- David Rundblad, June 29 2015, 2 years $2M: Signed by Stan Bowman. He played 9 games scoring 2 PTS before “this contract was terminated”. Thanks Cap Friendly Geek.
*- Viktor Tikhonov, July 1 2015, 1 year $1M: Signed by Stan Bowman. Played 50 games and scored 6 PTS. That’s not worth a million dollars dude.