The best posts always start with a question or questions that I don't know the answer to, and this one began with a few doozies: How many players win the Stanley Cup anyway? Has that number changed, on a percentage basis, over time? And what are the chances that a player like Marian Hossa, 30 years old and in the prime of his career, gets shut out?

It took me a couple days to cobble this together, with some major assistance for the raw data from stats maestro Gabe Desjardins, but I've finally got an answer: Of the 6,400-some players to have played in the NHL in the league's 90-plus year history, 14 per cent won at least one Stanley Cup championship in their career.

It adds up to 917 players, with Mr. Hossa and a few others potentially joining the club later tonight.

Those are the big picture numbers, and they tell us only a little of the story. Part of the problem is that they include about 200 players who were born before World War I, in an era when close to 40 per cent of the players in the league would, at some point, win a Cup.

What I started with was a look at all NHL players by birth year, along with a figure indicating how many players born in that particular year won a championship at some point in their career. Breaking these birthdates down into five-year segments, beginning with players born between 1900 and 1904, here's a graphical representation of the percentage of players per segment that won a Cup in their career:

Keep in mind that these dates are based on birth years, meaning that if you're looking for landmark years, start with 1950, which would have been about the first generation of players to play exclusively in a post-Original Six league. Prior to that point, with only six teams, a ton of NHLers were able to at some point win a championship in large part due to just how small the league was.

As you can see, the percentage of players who won Cups in the era immediately after expansion did dip to a low point (1950-59 birthdates), but there's a big-time recovery in the early '60s generation that included the likes of Wayne Gretzky (1961), Mario Lemieux, Steve Yzerman (both 1965) and other similarly aged players who have all since left the league (except Chris Chelios).

Here's a close up, year-by-year breakdown of the percentages from 1950 onwards:

The first thing to note is that we can pretty much ignore players from 1979 onward, as they are all 30 or under and may still be able to win a Cup. It's very tough to project exactly where the 30-team generation of players will fall in at this point.

Going back on the chart to its peak, however, in 1964, we see that an incredible 23 per cent of players born in that year wound up winning a championship in their career — despite the fact the league ballooned from 12 to 21 teams between 1970 and 1979.

Why the Cup boom around '64?

1. These players entered the league around 1983-84, near the end of the dynasty era, and were in their prime by 1989. Between that season, when the Flames won, and the 1999 playoffs, when the Stars did, nine different teams took home the Cup in 11 seasons. For a league that had previously had one team (the Canadiens) win 15 Cups in a 24-year span, this was a record level of parity.
   
   
2. Players born in and around 1964 would have been the first beneficiaries of more liberalized free agency. Bob Goodenow came to power at the NHLPA in 1992, when these players were about 28 years old, and ushered in an unprecedented era of veterans signing big-ticket contracts with well moneyed teams (not to mention all the rental players changing teams at the trade deadline). Many of those clubs won, and the revolving rosters did wonders for players attempting to get their names on Lord Stanley's Mug.
   

There's another steep jump in there nine years later, for players born in 1973, and this group would have spent its entire NHL existence under the leadership of a stronger union (i.e. no Eagleson). It's also likely that many players toward the end of their careers — as these players are now at around age 36 — would attempt to relocate to win a Cup, something that would skew the results.

So, how hard is it to win the Stanley Cup? Well, only somewhere between 10 and 15 per cent of players born in the last 60 years have managed to do so — and that could easily be a number that trends downward in a league with 30 teams and franchise players getting locked up on long-term deals. 

Only about 90 or so of the players currently in the NHL are likely to win a championship in their careers, a relatively exclusive club Hossa could join tonight.