Now that Section 8.9(b) has been analyzed regarding the Tomas Hyka situation, there seems to be a lot of confusion regarding why Sergei Bobrovsky wasn't affected by the same rule. Bobrovsky was signed as an Undrafted Free Agent, but happened to be 21 at the moment of the signing, when the rule clearly affects European players under 22. Compounding the confusion is that a player's First SPC Signing Age in Article 9 is listed as being calculated on September 15th, and Bob's 22nd birthday wasn't until September 20th.
So how were we able to sign him?
To start with, one of the major sources of confusion in the NHL CBA is the word "age". There are no less than 4 distinct and potentially contradictory definitions for age throughout the document; so you have to work hard to ensure that any interpretation is using the correct one.
In this case, the restrictions that we've been looking at are in Article 8. So we need to look for the proper definition of age for that article, and we find in 8.10:
8.10 Age of Players. As used in this Article, "age 18" means a Player reaching his eighteenth birthday between January 1 next preceding the Entry Draft and September 15 next following the Entry Draft, both dates included; "age 19" means a Player reaching his nineteenth birthday by no later than September 15 in the calendar year of the Entry Draft; "age 20" means a Player reaching his twent ieth birthday by no later than December 31 in the calendar year of the Entry Draft; "age 21" means a Player reaching his twenty-first birthday by December 31 in the calendar year of the Entry Draft and "age 22" means a Player reaching his twenty-second birthday by December 31 in the calendar year of the Entry Draft.
By the terms of Article 8, Bob would be '22' for the 2010 Entry Draft.
In 8.4, it is defined which players are draft eligible:
8.4 Eligibility for Claim.
(a) All Players age 18 or older are eligible for claim in the Entry Draft, except:
(i) a Player on the Reserve List of a Club, other than as a try-out;
(ii) a Player who has been claimed in two prior Entry Drafts;
(iii) a Player who previously played in the League and became a Free Agent pursuant to this Agreement;
(iv) a Player age 21 or older who: (A) has not been selected in a previous Entry Draft and (B) played hockey for at least one season in North America when he was age 18, 19, or 20 and shall be eligible to enter the League as an Unrestricted Free Agent pursuant to Article 10.1(d); and
(v) a Player age 22 or older who has not been selected in a previous Entry Draft and shall be eligible to enter the League as an Unrestricted Free Agent pursuant to Article 10.1(d).
In 2010, Bob was going to fall under (v), so he was not eligible for the upcoming Draft. But wait, we signed him on May 6th, 2010. The draft hadn't happened yet! True, but his contract didn't actually take effect until the start of the following season on July 1st, just like the other contracts signed that day.
Let's look back at 10.1(d):
(d) Draft Related Unrestricted Free Agents.
(i) Any Player not eligible for claim in any future Entry Draft pursuant to this Agreement and not on a Club's Reserve List shall be an Unrestricted Free Agent. Further, any Player eligible for claim in the Entry Draft, but who was unclaimed, shall be an Unrestricted Free Agent subject to the provisions of Section 8.9(b).
(ii) Each Player referred to in subsection (d)(i) above shall, during the period of his Free Agency in accordance with Section 8.9(b), if applicable, be completely free to negotiate and sign an SPC with any Club,
So I'm left with two possibilities: The first is that since Bob was going to be 22 for the upcoming draft, he falls into the first part of 10.1(d)(i) [italicized above], which makes him a straight up UFA. In that case, his eligibility to play in the league could fall under 8.9(a) instead of 8.9(b), because his contract didn't start until the beginning of the new season.
We have to look back at 8.9 a little bit closer:
8.9 Eligibility for Play in the League. No Player shall be eligible for play in the League unless he:
(a) had been claimed in the last Entry Draft, or was ineligible for claim under Section 8.4; or
(b) had been eligible for claim in the last Entry Draft, but was unclaimed, and:
(iii) had played hockey outside of North America in the prior season signed an SPC which was signed and registered with the League between the conclusion of the Entry Draft and the commencement of the next NHL Season.
(iv) The words "eligible for claim in the last Entry Draft" in subparagraph (b) above mean "eligible for claim in all rounds of the last Entry Draft." The words "the prior season" in subparagraph (i), (ii) and (iii) above mean "a full season prior to the last Entry Draft."
The second possibility comes from what I emphasized in 8.9(b)(iii). Bob's case may have followed the same logical progression through Articles 8 and 10 that Hyka's did; but because his contract didn't start until 2010-11, it may not count as having been registered with the league until after the 2010 draft occurred and the date range in 8.9(b)(iii) began.
As I said previously, this is a theory; but the fact that Bob was not eligible for 2010 draft, while Hyka will be eligible for the 2012 draft, is a very big distinction between the two cases. The only gray area with Bob is the fact that his contract was signed before the 2010 Draft officially occurred, but that only matters in regards to whether signing him in May was allowable or if they were technically supposed to wait until late June. Either way, it's completely different from Hyka's case.