NHL Free Agency Cannot Be Used For Immediate Gratification
As teachers and professors love to recite, history repeats itself.
There is no correct path to winning a Stanley Cup, but there is one to losing, and that is in free agency.
NHL teams are constantly trying to figure out how to gain an edge over their competition, and far too many use free agency as a mechanism for immediate gratification when it should be exclusively used as a way to build around, not create, a core.
History Shows…
Since 2014, no team has signed a newly acquired free agent to a contract worth more than $16 million total, $5 million annually, or longer than four years in free agency then gone on to win the Stanley Cup the following season.
In fact, after Tyler Bozak’s $15 million over three-year deal signed by the St. Louis Blues in 2018, the next highest deal by total value, term, and AAV was Evan Rodrigues’ $12 million over four year deal signed by the Florida Panthers in 2023.
David Perron signed a four-year, $16 million deal ($4 million AAV) with the Blues in 2018 following a season with the Vegas Golden Knights. However, he had previously played for the Blues from 2007-2013 and 2016-17.
After that, no contract surpassed $7.5 million total, $2.75 million annually, or a length of three years.
Even Stanley Cup runner-ups have followed this trend.
Since 2014, here are the largest contracts signed in the offseason to players who went on to lose in the Stanley Cup Final in Year 1 of their deal:
Anton Stralman (2014: $22.5M over 5 years)
Paul Martin (2015: $19.4M over 4 years)
John Moore (2018: $13.75M over 5 years)
Joe Pavelski (2019: $21M over 3 years)
Tyler Toffoli (2020: $17M over 4 years)
No other finalist since has signed a free agent for more than $10 million total in the preceding offseason.
This research only goes back to 2014 given a decade is a meaningful sample and roster strategies have developed since the NHL’s first couple seasons following the 2012-13 lockout.
An easy counterpoint may be how the salary cap ceiling has increased in this time, but the largest free agent deal signed in this span in terms of salary cap percentage is Bozak’s, which converts to just a $5.34 AAV in today’s dollars — a $340,000 annual jump.
It is possible other free agent deals signed under the same criteria since the NHL implemented a salary cap in 2005-06 surpassed this number, but the thesis stands true since at least 2014.
Understanding The Argument
None of this is to say the act of signing a player in free agency is inherently bad.
The Panthers have been as active as anyone in recent free agency, and have made three consecutive Stanley Cup Finals, winning two of them.
The Panthers also gave the largest ever free agent contract to a goaltender in 2019 when they inked Sergei Bobrovsky to a seven-year deal worth $70 million ($10 million AAV).
Of course, the Panthers have zero regrets, but this contract is an exception, as most Stanley Cup-winning goaltenders have been signed to deals a fraction of Bobrovsky’s.
This is not to say every contract signed in free agency is destined to be bad, either.
During free agency in 2024, contracts such as Shayne Gostisbehere’s three-year, $9.6 million ($3.2 million AAV) with the Carolina Hurricanes and Anthony Stolarz’s two-year, $5 million ($2.5 mill AAV) with the Toronto Maple Leafs have aged well thus far.
However, signing a new player to a long-term deal to play a prominent role on your roster is yet to result in immediate gratification, which is typically the goal of the larger signings.
How to Successfully Navigate Free Agency
A failed free agent signing can be attributed to countless factors, like a necessary acclimation period to learn a new system, the inevitable production aging curve that links most skaters to a decline in performance around 30-years-old (average age of an unrestricted free agent signing in the NHL is 28.65 years old, median is 28), or my personal belief: the best rosters consist of those playing for something more than a ring: a chance to hoist Lord Stanley before heading into negotiations on a new contract.
Stanley Cup-winning teams almost always consist of players on expiring contracts, which then typically leads such players to hitting free agency and receiving major paydays on deals worth more than their value.
Following the Panthers’ Stanley Cup victory in 2024, a chunk of their roster hit unrestricted free agency:
Brandon Montour signed a seven-year, $50 million deal ($7,142,857 AAV) with the Seattle Kraken, Vladimir Tarasenko signed a two-year, $9.5 million ($4.75 million AAV) deal with the Detroit Red Wings, Oliver Ekman-Larsson signed a four-year, 14 million ($3.5 million AAV) contract with the Maple Leafs, among others.
Depth pieces such as Kevin Stenlund, Nick Cousins, Ryan Lomberg, and Steven Lorentz were also highly coveted.
How did GM Bill Zito replace these players?
By adding upside on short deals and/or through players with something to prove, evident in his signing of the recently bought-out Nate Schmidt, and his trade for Seth Jones, who everyone had written off following his struggles with the bottom-feeding Chicago Blackhawks.
Jones averaged 25:30 of ice time per game in the playoffs, 91 seconds more than any other Panther, en route to winning his first Stanley Cup. Schmidt ranked 11th in goals per 60, fourth in primary assists per 60, and third in points per 60 among defensemen in the playoffs (min. 150 TOI).
This was not the first time Zito did this, either, as he signed Ekman-Larsson following his buyout in 2023 for just $2.25 million on a one-year deal.
The Salary Cap Era
All of these ideas converge on a central idea: Stanley Cups are won through value, not talent.
In the modern NHL with a hard salary cap, no team can go out and sign whichever player they desire.
Zito knows this, which is why he prioritized signing players like Schmidt in 2024 and Ekman-Larsson in 2023.
He knows it is better to sign a player he believes to be worth $3 to $4 million for $1 or $2 million, rather than give the $7 million player a “fair” deal.
While Jones may not have been worth $9.5 million, he knew acquiring him at a $7 million cap hit following salary retention would carry upside.
The same could be said for the historic Jonathan Huberdeau, Mackenzie Weegar, and Matthew Tkachuk blockbuster, where Zito passed on giving Huberdeau a deal worth over $80 million in favor of adding Tkachuk on a more favorable contract.
Over the past few offseasons, Zito’s strategy has been all about this idea of value, adding cheap talent for minimal term as opposed to his peers who go big-game hunting.
As a result, he has two Stanley Cup rings on his hand.
Building Value
Since the salary cap’s implementation, this premise of acquiring value is why building a Stanley Cup winner is often easier through the draft and trades. Young players have limited leverage in contract negotiations, and trade acquisitions typically come with players on predetermined deals.
Free agency is quite literally market value, making it more difficult to find players who can/will outperform their cap hit.
Zito’s decision to go after players recently bought out further extends this idea, as such players are getting paid elsewhere and could be more willing to take a cheaper deal.
This Idea Trend Transcends Free Agency
Free agency brings cap flexibility and infinite possibilities, and it is during this window GMs can get reckless, handing out contracts that quickly become costly.
The GMs who remain patient and take advantage of a frenzied market, like Zito, consistently come out ahead.
The same logic applies on the trade front.
The teams that win trades are the ones that time their moves well.
If you are going to sell, do it when demand peaks, either in the lead-up to the trade deadline or shortly after free agency begins while rival GMs are scrambling after missing out on top targets.
Moves at the deadline require more precision, but the key lies in knowing the player you are moving and the availability of comparable players across the league.
An example of this will be teams trading away centers and right-handed defenseman during the 2025 offseason, as both positions have a weaker free agent class.
When comparable players get moved, there are fewer suitors. If you wait until all suitors are gone, the player’s value plummets, but if you know there are limited comparable players, you can be more patient.
Conversely, teams looking to buy should aim to strike at the draft or deadline.
At the draft, teams have an idea of who will hit free agency and may look to offload money to reel in a big fish.
At the deadline, targeting sellers without long-term plans for their assets — usually veterans or players on expiring contracts — will force opposing GM’s hands.
The Data
Below are all relevant free agency transactions from Stanley Cup winners in the offseasons leading into their victory.
While no one data point can directly correlate to winning a championship, there is a strong connection between those who avoid handing out major contracts in free agency and those who win Stanley Cups.
Relevant Preceding Free Agency Transactions from Stanley Cup Winners (RFA’s included):
2024-25: Florida Panthers (Free Agency started on July 1 in 2024)
Tomas Nosek signed one-year, $775,000 on July 1
Chris Driedger signed one-year, $795,000 on July 1
A.J. Greer signed two-year, $1.7 million ($850,000) on July 1
Dmitry Kulikov signed four-year, $4.6 million ($1.15 million AAV) on July 1
Sam Reinhart signed eight-year, $69 million ($8.625 million AAV) on July 1
Jesper Boqvist signed one-year, $775,000 on July 2
Nate Schmidt signed one-year, $800,000 on July 2
Anton Lundell signed six-year, $30 million ($5 million AAV) on July 3
2023-24: Florida Panthers (Free Agency started on July 1 in 2023)
Oliver Ekman-Larsson signed one-year, $2.25 million on July 1
Kevin Stenlund signed one-year, $1 million on July 1
Mike Reilly signed one-year, $1 million on July 1
Niko Mikkola signed three-year, $7.5 million ($2.5 million AAV) on July 1
Anthony Stolarz signed one-year, $1.1 million on July 1
Dmitry Kulikov signed one-year, $1 million on July 1
Evan Rodrigues signed four-year, $12 million ($3 million AAV) on July 2
Eetu Luostarinen signed three-year, $9 million ($3 million AAV) on July 25
2022-23: Vegas Golden Knights (Free Agency started on July 13 in 2022)
Brett Howden signed one-year, $1.5 million on July 13
Reilly Smith signed three-year, $15 million ($5 million AAV) on July 13
Nicolas Roy signed five-year, $15 million ($3 million AAV) on August 8
Paul Cotter signed three-year, $2.325 million ($775,000 AAV) on August 13
Phil Kessel signed one-year, $1.5 million on August 24
Nicolas Hague signed three-year, $6,882,450 million ($2,294,150 million AAV) on October 10
2021-22: Colorado Avalanche (Free Agency started on July 28 in 2021)
Darren Helm signed one-year, $1 million on July 29
Tyson Jost signed two-year, $4 million ($2 million AAV) on July 30
Ryan Murray signed one-year, $2 million on August 2
Logan O'Connor signed three-year, $3.15 million ($1.05 million AAV) on September 22
Jack Johnson signed one-year, $750,000 on October 10
2020-21: Tampa Bay Lightning (Free Agency started on October 9 in 2020)
Luke Schenn signed one-year, $800,000 on October 9
Pat Maroon signed two-year, $1.8 ($800,000 AAV) million on October 9
Ross Colton signed one-year, $700,000 on October 9
Mikhail Sergachev signed three-year, $14.4 million ($4.8 million AAV) on November 25
Jan Rutta signed two-year, $2.6 million ($1.3 million AAV) on December 22
Erik Cernak signed three-year, $8.85 million ($2.95 million AAV) on December 22
Mathieu Joseph signed two-year, $1.475 million ($737,500 AAV) on December 23
Anthony Cirelli signed three-year, $14.4 million ($4.8 million AAV) on December 24
2019-20: Tampa Bay Lightning (Free Agency started on July 1 in 2019)
Luke Schenn signed one-year, $700,000 on July 1
Curtis McElhinney signed two-year, $2.6 million ($1.3 million AAV) on July 1
Carter Verhaeghe signed one-year, $700,000 on July 5
Cedric Paquette signed two-year, $3.3 million ($1.65 million AAV) on July 5
Andrei Vasilevskiy signed eight-year, $76 million ($9.5 million AAV) on July 29
Kevin Shattenkirk signed one-year, $1.75 million on August 5
Pat Maroon signed one-year, $900,000 on August 24
Brayden Point signed three-year, $20.25 million ($6.75 million AAV) on September 23
2018-19: St. Louis Blues (Free Agency started on July 1 in 2018)
Chad Johnson signed one-year, $1.75 million on July 1
David Perron signed four-year, $16 million ($4 million AAV) on July 1
Tyler Bozak signed three-year, $15 million ($5 million AAV) on July 1
Robby Fabbri signed one-year, $925,000 on July 3
Jordan Binnington signed one-year, $$650,000 on July 6
Oskar Sundqvist signed one-year, $700,000 on July 6
Dmitrij Jaskin signed one-year, $1.1 million on July 7
Pat Maroon signed one-year, $1.75 million on July 10
Joel Edmundson signed one-year, $3 million on July 24
2017-18: Washington Capitals (Free Agency started on July 1 in 2017)
Evgeny Kuznetsov signed eight-year, $62.4 million ($7.8 million AAV) on July 3
Devante Smith-Pelly signed one-year $650,000 on July 3
Andre Burakovsky signed two-year, $6 million ($3 million AAV) on July 4
Travis Boyd signed one-year, $650,000 on July 5
Phillip Grubauer signed one-year, $1.5 million on July 6
2016-17: Pittsburgh Penguins (Free Agency started on July 1 in 2016)
Chad Ruhwedel signed one-year, $575,000 on July 1
Justin Schultz signed one-year, $1.4 million on July 13
Matt Cullen signed one-year, $1 million on August 17
Matt Murray signed three-year, $11.25 million ($3.75 million AAV) on October 20
2015-16: Pittsburgh Penguins (Free Agency started on July 1 in 2015)
Conor Sheary signed two-year, $1.85 million ($925,000 AAV) on July 1
Brian Dumoulin signed two-year, $1.8 million ($900,000 AAV) on July 9
Beau Bennett signed one-year, $800,000 on July 15
Eric Fehr signed two-year, $6 million ($2 million AAV) on July 28
Matt Cullen signed one-year, $800,000 on August 6
You can check out more of Michael’s work at The Hockey News, follow him on X (michaelost13), Instagram (CoreNHL) or contact him directly at Michael.ostrower@gmail.com
Incredibly relevant, incredibly useful. Thanks!
No wonder Jake Guentzel’s 63 million contract didn’t work for us last year. I wonder what history shows for big contracts during their second year? No pressure to look that up—just wondering out loud.
Thanks for your work.