Winners and losers of Kirill Kaprizov's NHL record-setting contract

The Minnesota Wild handed out the largest contract in NHL history on Tuesday to star winger Kirill Kaprizov, as the 28-year-old will earn $136 million on an eight-year term through the 2033-34 season.

It's a deal worth more in total money that the one Alex Ovechkin signed with the Washington Capitals ($124 million) in 2008, and carries a higher average annual value (AAV) than the one signed by Leon Draisaitl with the Edmonton Oilers ($14 million) last September.

It's a contract that has sent shockwaves through the NHL. Some will benefit from its repercussions. Some will not. Here are the winners and losers of the Kaprizov contract, as we see them:

Winner: Bill Guerin

It was Guerin that finally got Kaprizov to leave the KHL for the NHL in 2021, succeeding where two previous Wild GMs had failed. Now he's the guy that's helped convinced Kaprizov to stay in Minnesota.

Guerin faced some enormous challenges in getting this done. One of them was the lure of unrestricted free agency under a rising salary cap, as Kaprizov wouldn't have suffered from a lack of suitors. Some of those suitors might have been more appealing than the Wild: As one NHL agent told ESPN, the Wild's status as a mid-tier Stanley Cup contender and Minnesota not being "a destination" for stars worked against them. Kaprizov had the hammer in negotiations, as was evidenced by the windfall he eventually received.

But Guerin also had some advantages here. His team could give Kaprizov the eighth contract year that the player reportedly wanted out of his next deal. He also had the financial backing of ownership to offer the richest contract in NHL history -- $128 million earlier in September -- and then increase that offer when Kaprizov didn't sign.

Guerin also benefitted from having Kaprizov's contract come up before a major change in the CBA rules. His contract pays out $128 million of his money in annual signing bonuses. That's 94% of its value. Starting in Sept. 2026, contracts will only be able to offer signing bonuses worth 60% of the "aggregate compensation payable under the contract."

Guerin landed the plane at time when many felt Kaprizov's initial rejection of a record contract was his rejection of the franchise. Whether you agree with the compensation or not, give credit where it's due: He got it done.

Loser: Kevin Cheveldayoff

Since 2021-22, Kyle Connor has scored just five fewer goals (153) than Kaprizov (158), having played 44 more games than the Minnesota winger. That's on a 14.2% shooting percentage. Simply put, the 28-year-old Jet winger is as elite a goal-scorer as you'll find on the wing -- and as an unrestricted free agent next summer, should be compensated as such.

The question is whether that'll happen in Winnipeg, where he's entering his 10th season, or elsewhere.

If Connor was waiting for a salary domino to fall, this one landed with a sonic boom. Jets GM Kevin Cheveldayoff just watched Kaprizov reset the market for a player that scored 41 goals and had 56 assists for a career best 97 points in 82 games.

Cheveldayoff has done a masterful job retaining other stars like goalie Connor Hellebuyck and Mark Scheifele, both at $8.5 million AAV over seven seasons. Market conditions were more favorable to the Jets when they re-upped in 2023. They aren't now, thanks in part to Kaprizov.

The conundrum for Cheveldayoff and the Jets: Is Connor worth that money?

"He scores goals, but gives a lot back," one NHL executive said.

Winner: Paul Theofanous

Wild owner Craig Leipold told The Athletic on Tuesday that the team was still convinced Kaprizov wanted to re-sign even after he didn't agree to an eight-year, $128 million contract extension offer on Sept. 9.

"He never raised the money issue. That was always the agent," Leipold said. "So, I mean, I think we always thought that we're going to get this thing done, and we thought, at least in the last week or so, 17 was the number."

Theofanous, Kaprizov's agent, is a legendarily tough negotiator. He not only managed to get another $8 million added to an offer that would have already set a new NHL contract value record, but he negotiated a contract structure that pays Kaprizov $128 million in "buyout-proof" bonus money. Theofanous dug his heels in and won huge, despite the Wild's belief that Kaprizov wouldn't take this to free agency.

Loser: Player movement

The era of player retention continues.

The upper limit of the NHL salary cap this season is $95.5 million. It's been estimated that the ceiling will be at least $104 million in 2026-27, the first time the NHL's salary cap will have crested over the century mark. Some predicted this inflation would lead to a spike in player movement, as teams had more to spend on acquiring talent.

On the contrary, the rising cap has seen teams retain their players throughout the offseason, no longer sweating out the pressure points that the cap created. Kaprizov is the latest name to stay where his stuff is, and he's likely not the last.

Winner: Getting locked in early

Hart Levine of the salary cap site Puck Pedia believes that hockey fans just have to accept that this is the new normal under the salary cap.

"It's a big number, but we just have to get used to living in a world where the cap is going up each year. It's going up 9% from this year to next year," he told me.

It's all about context. Heck, even Kaprizov's deal might look like a bargain in the next few seasons.

Take Draisaitl's contract that he signed last September. Levine says that under next year's salary cap, Draisaitl's contract would have been worth $15.25 million against the cap. Conversely, if you took Kaprizov's contract and put into current cap dollars, the AAV would be around $15.6 million.

One NHL executive likened the rise in the salary cap to a "tidal wave" that'll just keep adding more and more large contracts as it grows. Which means the key for teams is locking players in before that wave crests.

When discussing good cap management with some NHL sources, one team that came up multiple times was the Carolina Hurricanes.

Their front office, now led by GM Eric Tulsky, has locked up several players to long-term deals ahead of the dramatic salary cap increase: Forwards Sebastian Aho ($9.75 million through 2031-32), Seth Jarvis ($7,420,087 through 2031-32) and Logan Stankoven ($6 million through 2033-34), as well as newly acquired defenseman K'Andre Miller ($7.5 million through 2032-33) and forward Nikolaj Ehlers ($8.5 million through 2030-31).

The Canes have their core locked up long-term at a reasonable rate, and the flexibility to still go after big players via trades as they've done the last two seasons with Jake Guentzel and Mikko Rantanen.

Speaking of which ...

Losers: Mitch Marner and Mikko Rantanen

Kaprizov's contract will no doubt continue the dialogue about NHL cities with high income taxes and NHL cities that don't have income taxes, a.k.a. the teams that happen to be winning Stanley Cups with some frequency lately.

According to an analysis by the Tax Foundation, Minnesota has the fifth-highest top income tax rate in the U.S., at 9.85%. There's no question that's a factor in Kaprizov getting $136 million over eight seasons, because he wouldn't have gotten that same number in a no-tax state. Jeff Marek of Daily Faceoff spoke with one player agent who said Kaprizov's average annual value in a place like Florida would have been around $14 million.

If that's the case, then Kaprizov still would have made more annually than Mitch Marner of the Vegas Golden Knights and Mikko Rantanen of the Dallas Stars, who both signed mega-contracts in the last year worth $12 million against the cap through 2032-33.

Marner's points-per-game average of the last three seasons was equal to Kaprizov's (1.24) while Rantanen's was right behind them (1.22). If either of them had the power of clairvoyance and could see what Kaprizov just earned, what would those contracts have looked like?

Winner: Kirill Kaprizov

We must obviously shout out the man himself, who set a new standard for NHL contracts in both overall value and average annual value. From a production standpoint, he's among the best offensive hockey players in the world: He plays to a 50-goal pace, is a dynamic playmaker and shown to be a more committed defensive player than one might assume given his gaudy stats.

But there's one number that's never added up for Kaprizov, and that's games played. The winger has played over 80 games once in his NHL career, back in 2021-22 when finished seventh in the MVP voting. Last season saw him limited to 41 games. He's 28 years old, turning 29 next April.

Again, it's a credit to Kaprizov that he has still managed to post astounding numbers despite those injuries. But for this level of investment, the Wild need him on the ice and not in the press box. Minnesota was 63-41-12 with Kaprizov in the lineup over the last two seasons and 21-23-4 without him. He's a difference-maker.

Loser: Connor McDavid

The most complicated contract decision in the NHL just got a little more complicated.