Rare Bird: The Penguins' Sidney Crosby is one of the few NHL players making seven figures off the ice. Pittsburgh's star center hauls in an estimated $5.5 million annually from endorsements and other business endeavors.

On a breezy September afternoon in Los Angeles, three days after Sidney Crosby signed a two-year contract extension with the Pittsburgh Penguins, Pat Brisson can only chuckle when asked about the $17.4 million deal. “What am I going to tell you?” he says in his French Canadian lilt. “On the record, he could have had more money.”

Brisson would know. The 59-year-old superagent has negotiated $1.4 billion in active playing contracts—the best mark in the NHL—for stars including the Colorado Avalanche’s Nathan MacKinnon, the New Jersey Devils’ Jack Hughes and the Vancouver Canucks’ Elias Pettersson. His agency, CAA, where he is co-head of a roughly 30-employee hockey group alongside JP Barry, has around 100 NHL players on its roster and $2.1 billion in active player contracts under management, a number surpassed only by Newport Sports Management’s $2.3 billion, according to contract database PuckPedia. Among CAA’s clients are five of the NHL’s 10 highest-paid players this season.

But Brisson also knows that, ultimately, his job is to make his players happy—even if it means taking less money than they could have made on the open market. And while CAA is most certainly a business—it has topped Forbes’ ranking of the most valuable sports agencies for nine consecutive years and was purchased by French luxury goods mogul François-Henri Pinault’s investment firm for a reported $7 billion last year—it similarly understands when finances need to take a backseat to its goal of being a 360-degree operation for its clients (or as CAA Sports co-head Howard Nuchow puts it, “to be important to our players in as many areas as we can”).

That focus on services, an agency hallmark since CAA Sports launched in 2006, could mean helping a player build up a social media presence or launch a business. Or it could just mean hooking up the player with tickets to a basketball game or a Broadway show—whatever it takes to recruit, and retain, clients, even when there’s a significant upfront cost and no payoff on the immediate horizon.

For now, marketing remains a piece of that money-losing equation, with limited revenue........

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