Gaudreau and Monahan not signed yet? Don’t panic, it’s complicated

On July 1, two of the best draft picks in the history of the Calgary Flames became restricted free agents. Calgary’s 2011 fourth round pick Johnny Gaudreau and 2013 first round pick Sean Monahan, together the two highest-scoring Flames last season, have been without contracts since Canada Day. Given that the dynamic duo is going to be eating up a large chunk of the Flames’ salary cap and that they’re likely to get two of the richest deals in the history of the franchise, the lack of signing announcements has caused some hand-wringing and brow-furrowing among the fanbase.

Why are these deals taking so long? Shouldn’t they been done by now?

Relax. It’s complicated.

The first problem that the Flames have to solve with each camp is the length of the deal. The maximum length for each is eight years, which would take Gaudreau until he’s 30 and until Monahan’s 29. The main key in length discussion is how many years of unrestricted free agency each side is comfortable with buying, as you’d expect the average annual value of the contract to move upwards for each season of free agency a player forgoes.

You’d expect the conversation to go something like this:

Each player’s representatives have an incentive to have their deal expire juuuust a bit before the other one does, as that way they would have the opportunity to get their big “Please don’t go to free agency” raise before the other guy does (and effectively get the maximum piece of the Flames salary cap pie rather than negotiate against each other). That’s probably something that plays into it.

Bear in mind that Don Meehan, Monahan’s agent, has a reputation as a shark. He also reps Jarome Iginla and Steven Stamkos. (Gaudreau is represented by Lewis Gross, who previously repped Martin St. Louis and currently extols the virtues of Torey Krug and Brandon Saad.)

Let’s just say, for argument’s sake, that the Flames and both sides have agreed on general terms. They’ve figured out how many years and they’ve agreed in principle on similar contracts from comparable players. For argument’s sake, let’s say that Monahan wants eight years at $6.5 million and Gaudreau wants eight years at $7.5 million. Once those things have been nailed down, two things need to be figured out: year-to-year salary distribution (e.g., how much money will be paid out in a given league year) and how much is paid in salary and how much in bonuses.

The current CBA can potentially expire at the end of the 2021-22 season and agents are understandably wary about salaries being rolled back. So, we’ve seen the rise of something known as “Lockout Proofing.” Rather than paying out the $7.5 million equivalent to Gaudreau every season in salary (for example), the sides could negotiate a combination of salary and signing bonuses. Salary can be rolled back, but bonuses can’t. So the amount paid out each season and the composition of what is paid out is a huge factor in current negotiations league-wide.

And once you’ve settled on a contract length and how much is being paid out (and how much is salary or bonuses), then each side has to haggle over no-trade and/or no-movement clauses. (They can kick in once the players are into their UFA seasons).

In short? On their own, the Monahan and Gaudreau negotiations are each the most important contract in the history of the Flames franchise. These are hugely valuable assets that the club is trying to sign long-term, and the negotiations are not only going on during a hugely tumultuous time in the NHL’s history – on the cusp of expansion and as the end of the current CBA looms – but these important negotiations are concurrent to each other.

Brad Treliving is playing two simultaneous hands of high-stakes poker. He’s going to be handing out the two most expensive deals in the history of the franchise. And he’s negotiating with two camps that have an incentive to try to wrangle and wriggle their way to more favourable deals than the other is getting.

Deals will get done. Gaudreau falls into a weird black hole in the CBA where he hasn’t played enough seasons to receive offer sheets, and the Flames would definitely match any offer sheet given to Sean Monahan. If the contracts were simple, they’d be done by now. But they’re not. They’re arguably the most complex negotiations in franchise history.

Step back from the ledge. Take a deep breath. Relax. The situation is complicated.