1: Was the player arbitration-eligible?
2: How many (if any) UFA years did the contract signed extend through?
3: What are comparable RFA players around the league making?
Obviously, the second question should be asked much less awkwardly than it is asked here. Let us examine the contract of Dave Bolland, who signed for 16.875 million dollars over five years with the Blackhawks.
Was the player arbitration eligible?
Answer: No. Bolland signed an entry-level contract in 2007 age the age of 19 (or 20), and had 3 years of pro experience - a player who signs an entry-level contract between the ages of 18 and 20 needs to have 4 years of pro experience before opting for arbitration.
We ask this question because arbitration allows for a player to be paid more - players without arbitration eligibility essentially have no bargaining power. Their only recourse is to sign an offer sheet with another team (or in another league) - otherwise, it is basically 'take it or leave it' from their team's GM.
How many UFA years does this contract extend through?
Answer: One. Assuming UFA rules stay the same after the next CBA is signed, Bolland would have been eligible to be unrestricted in July 2013 - this contract extends through July 2014.
We ask this question because RFA players are cheaper than UFA players - signing a player through UFA years keeps his price down.
What are comparable players around the league making?
Answer: This is more difficult to say. Jordan Staal's contract no doubt had a hand in this - Staal is making $4M/season until 2013. Joe Pavelski signed a 2 year, 3.275 million dollar deal as a non-arbitration eligible player in 2008 - his next contract will likely pay him between 3.5 and 4.5 million dollars a season.
The fourth question is one that shouldn't necessarily be germane but becomes so:
Will the player get better during the course of the contract?
Answer: The Blackhawks have to hope so, and are certainly counting on it. Bolland had 1.37 Shots On Goal Per Game (hereafter S/G) last season - if he continues that rate, he is unlikely to score more than 20 goals a season. The good news for the Hawks is that Bolland did not receive much power play time - if he does next season, expect his S/G and goals to rise. The Hawks have to be hoping his S/G rises to around 2 - around 2, and Bolland should be expected to score between 16 and 24 goals a season in a normal year, and closer to 30 in an abnormal year (like this past one). Bolland already appears to be an excellent assist man, as he averages close to 1 every 3 games, so his normal season may look like 20 goals and 30 assists, an excellent output for a third line center.
Did the Hawks make a good deal?
Answer: Almost certainly not. They ate up 3 arbitration-eligible years, a UFA year, and an arbitration-ineligible year. They must have very high hopes indeed and worry that a 60 point season for Bolland would mean a favorable comparison to a contract like Jordan Staal's. But with a career S/G of 1.33 so far, it is unlikely that Bolland has such a large offensive output. It is hard to predict what the NHL landscape will look like in July 2014 when Bolland is an unrestricted free agent, but it's hard to imagine him getting offers well above $5 million per season if he ever makes it there, so basically all the money saved in season 5 of the deal (by paying RFA instead of UFA prices) equals the money squandered in season 1 by signing him to this long-term deal. The Hawks would likely have been better served to try to sign Bolland to a deal not unlike that of Joe Pavelski's - there's not enough NHL information to conclude that Bolland will certainly be with 3.375M per season, and with the Hawks being in enormous salary cap trouble in 2010-11, Bolland may be first on the chopping block if he does not produce.