Jeremy Jacobs, owner of the Boston Bruins and chairman of the NHL Board of Governors
Some are interesting because of their circumstance—Jarmo Kekalainen, general manager of the Columbus Blue Jackets, is a great example as he is the first European GM in NHL history,
Others are intriguing because of their power and reach. One doesn't need to look beyond the likes of Jeremy Jacobs and super-agent Don Meehan for prime examples of incredibly influential people within the league.
Who else stands out as an absorbing figure in the NHL?
Paul Holmgren is arguably the most aggressive and fearless GM in the NHL right now. The corresponding deals that sent Mike Richards to the L.A. Kings and Jeff Carter to the Columbus Blue Jackets only cemented that reputation.
While he was much more quiet at the 2013 trade deadline, that doesn't ease the feeling that Holmgren always has his finger on a trigger somewhere. There's a sense that no one on the roster of his Philadelphia Flyers is untouchable, and that makes for some interesting speculation and fun conversation.
Jarmo Kekalainen was one of the main boardroom cogs that helped turn the St. Louis Blues into a Stanley Cup-contending team after a stint as one of the worst teams in hockey. His specialty is talent evaluation, and he was at least partially responsible for drafting players like Alex Pietrangelo, T.J. Oshie and Vladimir Tarasenko.
He's now the general manager of the Columbus Blue Jackets and is again working with John Davidson to rebuild a Central Division team from the ground up. Kekalainen is the first European GM in the history of the NHL, so there's an added interest in all the moves that he makes as he tries to make Columbus a hockey hotbed.
If his shrewd deal for Marian Gaborik is any indication, better days are just around the corner for the possibly playoff-bound Blue Jackets.
Brian Burke is a microphone magnet, and for better or worse, when he talks, people listen. He's a quote machine and always has something snarky or mildly condescending to say to the media.
He was unceremoniously fired from his position as GM of the Toronto Maple Leafs just before the 2013 campaign began, but that hasn't prevented Burke from stepping into the spotlight and raising eyebrows with bold statements like "I'm going to go somewhere else, I'm going to try and haunt this team" (per Dave Feschuk of the Toronto Star).
Brendan Shanahan might have the toughest and most controversial job in the NHL—I'm assuming that doling out punishment to players for illegal hits and slashes is tougher than being generally despised, which makes his job tougher than that of Gary Bettman.
The league is trying to cut back on concussions and head injuries in general without removing too much physicality from the game, and that job falls to Shanahan. He sets precedents for suspendible actions and is the public face of the disciplinary committee.
When the NHLPA brought Donald Fehr in to negotiate the new CBA, onlookers knew that a battle was brewing. While many didn't think that a lockout was on the horizon, Fehr got all of his troops on the same page and went to war.
I could watch the videos of Gary Bettman and his cronies throwing hissy fits all day—Fehr literally drove the NHL brass nuts to the point of public mental breakdowns and set a new bargaining standard for the PA.
John Collins is the NHL's chief operating officer (COO) and is the mastermind behind many of the league's most popular events and attractions.
Since leaving the NFL for his current job in 2008, Collins has brought the NHL Winter Classic to life, cut a deal with HBO for the remarkably entertaining 24/7 series and has aggressively sought to increase the league's digital viability with programs such as Game Center Live.
According to Sports Illustrated, over the first two years of his tenure alone he generated 66 percent more revenue through advertising and sponsorships.
Regardless, Jacobs is one of the most powerful and influential men in the NHL. He's the owner of the Original Six franchise Boston Bruins and is head of the NHL Board of Governors. Jacobs is charged with speaking for the collective ownership of NHL teams and is responsible for the league's business initiates and stances along with Bettman.
When he talks, you have to listen. The power he wields is second almost to no one, and he is just as responsible for the 2013 lockout as Pinky—er, Bettman.
If a player on your favorite team has been a holdout over the last two-plus decades, odds are Don Meehan and his Newport Sports Management Inc. represented him.
P.K. Subban and Drew Doughty are two of the more recent examples of the hard negotiating tactics that Meehan and his stable of agents have become known for, and the list of players who use Newport Sports Management to do their negotiating is staggering.
While it could be easy to jump to the conclusion that you don't like Meehan because of his tendency to have his clients holdout, he has built his empire from nothing and is an incredibly hard-working and diligent person.
If the hockey agent world has a Jay-Z, Meehan is it.
Ray Shero is one of the best GMs in the NHL and clearly has a knack for understanding how the NHL works under a salary cap. While other managers may be tempted to sit back and see what happens with their teams, Shero grabs the bull by the horns every single time.
If nothing else, come deadline day you know that at least one GM has a trick or two up his sleeve.