There are some predictable components when it comes to the NHL offseason. The draft is on a set day, and there's usually at least a mild consensus about who the top 30 or 45 players are—at least until the Calgary Flames take to the stage to make their pick.
Free agency is typically a two-day storm that blows up off of the shores of the draft, consuming all logic and sensibility for a 48-hour (or so) period.
The wild card is, and always has been, trades. They're always surprising, and they rarely happen the way we expect. A great example of this is the sudden Bobby Ryan-to-Ottawa trade at the recent draft. This, of course, after the Philadelphia Flyers courted the Anaheim Ducks for the better part of two years to land the sniper.
Rumors swirl year round, and deals usually take upwards of six or seven months to finally pan out. Some players will be moved before the puck drops on the 2014 NHL season. It's just a matter of who, and to where.
All salary cap information appears courtesy of Capgeek.com.