There has been a lot of confusion over the past few days about where the Leafs might be picking with Boston and Philadelphia's first rounders. Assuming that Brian Burke doesn't package those picks in some sort of deal, the Bruins' pick could be anywhere from 21st to 30th overall, and the Flyers' pick could be anywhere from 24th to 30th overall. (As I write this, neither Boston nor Philadelphia have been eliminated yet.)
I'll show you how we know this after the jump.
For starters, we already know who picks 1st through 14th, as they've already conducted the draft lottery for teams already eliminated from the playoffs.
The remaining order is determined by the Stanley Cup playoff results. Whichever team wins the Stanley Cup is awarded the 30th and last pick, while the runner-up is given the 29th pick. The teams eliminated in the conference finals are awarded the 28th and 27th picks, with the 28th pick going to the team with the better regular season record. Remaining division winners, then wild card teams are ranked next, filling in the 26th through 15th picks. In both cases, better records result in later picks.
It might require reading this a few times through to get a handle on things, especially since they use the term "wild card teams", but all they're getting at is playoff teams that aren't divisional winners. More or less like in the MLB.
So here are the obvious picks mentioned in the paragraph above:
30th: Stanley Cup Winner
28th: Team eliminated in the semi-finals with the better regular-season record.
27th: Team eliminated in the semi-finals with the worse regular-season record.
Now here's where things get a little funny. In the extremely unlikely event that the final four teams are all non-divisional winners, that is, that there isn't a single one of Boston, Detroit, San Jose, Philadelphia, or Vancouver left after the second round, the Bruins' pick is 21st, and the Flyers' is 24th. Each one would fall back four places.
Note that although Pittsburgh has more points than San Jose, Detroit, or Boston, since the Penguins are not divisional winners, they will pick earlier than all of the other three, unless they make it to the final four.
Since Boston has the fewest points out of all the divisional winners, for each other division winner that makes it to the final four, Boston's pick gets knocked back one spot (as, later in the draft). But, in Philly's case, because they have more points than all but two teams - Vancouver and Washington - if any of the other three remaining division winners (San Jose, Detroit, or Boston) get into the finals, it still helps their pick.