It happens every off-season despite numerous examples outlining how it usually ends in frustration and disappointment. It happens in most markets, and I see only two cases since 2006 where it worked out really well: Boston and Chicago.

Some turned out okay, but most have been utter disasters.

Let’s take a peek at the past decade of UFA long-term signings. Proceed with caution.

2012:
Ryan Suter: 12 years, $7.538m AAV with Minnesota.
Zach Parise: 12 years, $7.538m with Minnesota.
Matt Carle: Six years, $5.5m in Tampa Bay
Jason Garrisson: Six years, $4.6m with Vancouver
Jiri Hudler: Four years, $4m with Calgary.
PA Parenteau: Four years, $4m with Colorado.
Brandon Prust: Four years, $2.5m with Montreal.
Adam Burish: Four years, $1.8m with San Jose.

Hudler was the best signing by far. He was productive in Calgary. Parise and Suter were bought out of the final four years of their deal earlier this week. The most points Parise scored in Minnesota was 62. Suter was a solid defender for his eight seasons.

Carle and Parenteau were bought out after four and three seasons respectively.
Garrison had three solid seasons out of the six.
Prust was what Montreal expected. Physical, but didn’t provide much offence. Burish was banged up and scored two goals in three seasons in San Jose, before playing his final year in the AHL.

2013:
Nathan Horton: Seven years, $5.3m with Columbus.
David Clarkson: Seven years, $5.25m with Toronto.
Valtteri Filppula: Five years, $5m with Tampa.
Stephen Weiss: Five years, $4.9m with Detroit.
Ryan Clowe: Five years, $4.85m with New Jersey.
Mike Ribeiro: Four years, $5.5m with Arizona.
Rob Scuderi: Four years, $3.375m with Pittsburgh
Andrew Ference: Four years, $3.25m with Edmonton
Viktor Stalberg: Four years, $3m with Nashville.
Eric Nystrom: Four years, $2.5m with Nashville.
Matt Hendricks: Four yeras, $1.8m with Nashville.

Horton only played 35 games with Columbus before suffering a career-ending injury. Clarkson scored five goals his first season in Toronto, had 10 in 58 games in his second year before he was traded to Columbus for Horton. Basically just so Toronto could take the LTI contract of Horton. Clarkson played 26 games for Columbus before injuries ended his career.

Filppula was very good his first season in Tampa, and solid in his second when they went to the Cup final, but he then dropped to being a 30-point player and was traded midway through fourth season.

Weiss got injured his first season, then scored 25 points in year two and was bought out. He never played another NHL game.

Clowe played 43 the first season due to injuries. Then 13 in the second year before injuries ended his playing days. He was on LTIR after those 13 games.

Ribiero played one season in Arizona and was bought out after one year for “behavioural issues.” He signed a one year, $1.05m deal in Nashville and scored 62 points. Then signed a two-year deal worth $3.5m.

Scuderi played two years in Pittsburgh, before being traded. Andrew Ference played two years in Edmonton, then spent the final two years on LTIR.

Stalberg had 18 points his first season, then split time in AHL/NHL in second season and was then bought out.

Nystrom had 15 goals his first season, then 12 and seven points. He was bought out after third year.

Hendricks played all four seasons with Nashville and Edmonton. He or Filppula gave the best value for their contracts.

2014:
Matt Niskanen: Seven years, $5.57m with Washington.
Dave Bolland: Five years, $5.5m with Florida.
Brooks Orpik: Five years, $5.5m with Washington.
Michael Cammalleri: Five years, $5m with New Jersey.
Matt Moulson: Five years, $5m with Buffalo.
Anton Stralman: Five years, $4.5m with Tampa.
Benoit Pouliot: Five years, $4m with Edmonton.
Paul Stastny: Four years, $7m with St. Louis
Mikhail Grabovski: Four years, $5m with NYI.
Nikolai Kulemin: Four years, $4.187m with NYI.
Jussi Jokinen: Four years, $4m with Florida.
Mark Fayne: Four years, $3.625m with Edmonton.

Niskanen was very good for five season for Washington and a key part of their Cup in 2018. They traded him to Philly for Radko Gudas in the summer of 2019. Orpik also was solid in his role with Washington, although a bit overpriced. He was a solid third pair defender on the Cup team. He was bought out of the final year of his deal.

Stastny produced 46, 49, 40 and 53 points in his four years. He was dealt to Winnipeg at trade deadline in his final season. He was a solid player, but didn’t play like a $7m player. He and Niskanen were the best signings by far.

Bolland had 23 points in 53 games his first season, then only played 25 games in year two before being on LTIR the rest of the contract.

Cammalleri, Jokinen and Pouliot were bought out after three seasons. Moulson played three seaons in Buffalo, then spent the final two in the AHL.

Stralman had five solid seasons in Tampa. Not spectacular, just very steady.

Grabovski played two seasons before a concussion ended his career. He had 9-10-19 in his first year and 9-16-25 in his second. Kulemin played four seasons and produced a total of 37 goals, 79 points in 248 games.

Fayne played two season in Edmonton and the final two in the AHL.

2015:
Andrej Sekera: Six years, $5.5m with Edmonton.
Michael Frolik: Five years, $4.3m with Calgary.
Matt Beleskey: Five years, $3.8m with Boston.
Paul Martin: Four years, $4.85m with San Jose.

Sekera had two good years, then was injured and played parts of the next two seasons before being bought out after year four.

Frolik was productive for four seasons before being traded midway through the fifth season. He was slightly overpaid, but decent value for what he produced and how he defended.

Beleskey scored a career-high 37 points his first season, but then only eight in 49 games in year two. He had no points in 14 games in the third season, before they traded him to the Rangers while retaining 50% of his salary. Over the final three years of his deal he played 19 NHL games and the rest was in the AHL.

Martin’s first two seasons in San Jose were quite good as they went to the Cup Final in his first year. He got banged up in his third season, and was put on waivers and played 18 games in the AHL. He was bought out of the final year of his contract.

2016:
Milan Lucic: Seven years, $6m with Edmonton.
Kyle Okposo: Seven years, $6m with Buffalo.
Andrew Ladd: Seven years, $5.5m with NYI.
Loui Eriksson: Six years, $6m with Vancouver.
Frans Nielsen: Six years, $5.25m with Detroit.
David Backes: Five years, $6m with Boston.
Jason Demers: Five years, $4.5m with Florida
James Reimer: Five years, $3.4m with Florida.
Troy Brouwer: Four years, $4.5m with Calgary.
Mikkel Boedker: Four years, $4m with San Jose.
Matt Martin: Four years, $2.5m with Toronto.
Dale Weise: Four years, $2.35m with Philadelphia.

None of these deals worked out for the teams who signed them. Brouwer was bought out after two seasons. Lucic was traded to Calgary, Backes to Anaheim with Boston retaining 25%.

Reimer was probably the best deal in terms of value. Matt Martin didn’t pan out in Toronto, but when they traded him back to New York he fit in well on their energy line.

This year was the poster child for UFA signings gone wrong.

Alex Radulov: Five years, $6.25m with Dallas
Karl Alzner: Five years, $4.625m with Montreal.
Kevin Shattenkirk: Four years, $6.65m with NYR.
Nick Bonino: Four years, $4.1m with Nashville.

Radulov was very good his first three seasons. He got injured this past year and only played 11 games. We’ll see what happens this season.

Bonino had four very solid seasons in Nashville. For bang for your buck on the full term of his contract he is one of the better deals since 2012 among UFAs who signed 4+ years.

Shattenkirk was bought out after two years, while Alzner played one season in Montreal, then only 13 NHL games over the next two seasons (87 in AHL) and was bought of the final two years of his deal.

2018:
John Tavares: Seven years, $11m AAV in Toronto.
James Van Riemsdyk: Five years, $7m in Philly
James Neal: Five years, $5.75m with Calgary.
Jack Johnson: Five years, $3.25m with Pittsburgh
John Moore: Five years, $2.75m with Boston.
Calvin de Haan: Four years, $4.55m with Carolina.
Jay Beagle: Four years, $3m with Vancouver.
Antoine Roussel: Four years, $3m with Vancouver.
Leo Komarov: Four years, $3m with NYI.

Tavares has produced well, but Toronto has yet to win a playoff round with him. JVR has produced .072, 0.60 and 0.77 points/game in his three seasons. Solid production, but not worth $7m.

Neal struggled in Calgary and was traded for Lucic. He did score 24 goals in 84 games over two seasons in Edmonton, but is likely going to be bought out next week.

De Haan was traded to Chicago as a salary dump after one season. He likely won’t be protected in the expansion draft this weekend.

Johnson was bought out after two seasons. Moore has battled injuries and only played 61, 24 and 5 games in his three seasons with Boston. He had hip surgery this past March.

Beagle has six goals and 26 points in three seasons with Vancouver. He’s played 142 games and missed 65 due to injury. Roussel had decent production his first year with 31 points in 65 games, but since then he has 17 points in 76 games and missed 49 due to injury.

Komarov fits the role New York has him in, but he isn’t giving them much production. He has 11 goals in three seasons.

2019:
Artemi Panarin: Seven years, $11.64m with NYR.
Sergei Bobrovsky: Seven years, $10m with Florida.
Matt Duchene: Seven years, $8m with Nashville.
Brandon Tanev: Six years, $3.5m with Pittsburgh.
Tyler Myers: Five years, $6m with Vancouver
Mats Zuccarello: Five years, $6m with Dallas
Gustav Nyquist: Four years, $5.5m with Columbus
Semyon Varlamov: Four years, $5m with NYI.
Jake Gardiner: Four years, $4.05m with Carolina.
Joonas Donskoi: Four years, $3.9m with Colorado.
Micheal Ferland: Four years, $3.5m with Vancouver.
Brett Connolly: Four years, $3.5m with Florida.
Richard Panik: Four years, $2.75m with Washington.
Garnet Hathaway: Four years, $1.5m with Washington.

Panarin has been very productive thus far for the Rangers.
Myers has played the most 5×5 minutes in Vancouver the past two seasons. He has the seventh most points. He is being asked to do more than he should be.
Tanev got longer term than many expected, but for the first two years he has added some offence and added the energy they wanted.
Zuccarello has given Minnesota solid production thus far.
Varlamov has backstopped the Islanders to the third round of the playoffs in his first two seasons.
Donskoi has been a solid player with Colorado thus far. Good offence and possession numbers.
Hathaway has been excellent value in two seasons. He has chipped in some offence, has solid possession numbers and has a 53GF%, a 54xGF% and has played every game since signing.

But in only two years the other deals haven’t worked out.

Bobrovsky has a .902Sv% in 81 games over this first two seasons with Florida. Chris Driedger had a .931sv% in 35 games with the Panthers during that time. And now Florida has young Spencer Knight coming. The Bobrovsky deal won’t end well.

Duchene has 19 goals and 55 points in 100 games. There are rumblings he will be exposed in the expansion draft. He hasn’t come close to $8m in production.

Nyquist had a solid but not spectacular first season, but he didn’t play a game this year with a shoulder injury. He has been cleared to play next season.

Gardiner couldn’t crack the top six in Carolina this season.

Ferland only played 14 games due to concussion issues. His career is likely over unfortunately.

Connolly did score 19 goals his first season, but only played 21 games this year before he was traded to Chicago as a salary dump. Florida had to include Riley Stillman in the deal.

Panik was traded to Detroit at the deadline this season. He tallied 4-7-13 in 48 games between Washington and Detroit.

2020:
Alex Pietrangelo: Seven years, $8.8m with Vegas.
Torey Krug: Seven years, $6.5m with St. Louis.
Jacob Markstrom: Six years, $6m with Calgary.
TJ Brodie: Four years, $5m with Toronto.
Chris Tanev: Four years, $4.5m with Calgary.
Tyler Toffoli: Four years, $4.25m with Montreal.
Matt Martin: Four years, $1.5m in NYI.

Too early to tell. However, Montreal and Vegas and New York got excellent returns in year one.

Calgary will need more from Markstrom moving forward. He posted a .904sv% in 43 starts.

It is a sobering reminder of how free agency is rarely the place to complement a winning team. Washington is the only Cup winner who had long-term UFAs signed. Marian Hossa and Zdeno Chara were long-term deals that worked out as they played great, and the Blackhawks and Bruins won the Cup, but they are also Hall of Fame players. It is rare.

Between 2012-2018 there were 60 UFAs signed to 4+ year deals. So far 18 have been bought out and 12 finished their careers on LTIR or in the AHL. That is 50% and the only reason there weren’t more is because agents realized you could structure deals making them almost buyout proof. Think about that for a moment: Teams are willing to sign buyout proof deals. If the deal needs to be structured that way, isn’t that a sign it likely won’t work out? And I didn’t include players who were pending UFAs and re-signed with their team. Jeff Skinner comes to mind.

I never blame the players for signing these deals. We all believe we can be good, and I don’t know many who would say to their boss, “I’m not worth that much money.” However, they should also remember that Roberto Luongo did admit late in his long-term contract he wished he didn’t have it as it led to a lot of frustration.

The organizations need to understand that most long-term deals are crippling. Had many of these players been signed to shorter terms deals they wouldn’t have been nearly as bad. Benoit Pouliot would have been fine on a three-year term. Yes, he was injured, but he had been injury prone prior to signing the deal. You had to expect that could happen again, but signing him to five years crushed Edmonton.

It isn’t ideal to overpay in salary, but if you do that on a shorter term, the damage doesn’t have long-lasting effects down the road.

Free agency begins in less than two weeks. Successful teams will make prudent signings, while desperate teams will sign deals that might help for one or two seasons, but they will ultimately lead to disappointment and compounded pain in the future.

Accepting you have to overpay in free agency is not a successful business plan.