Guys that bet on themselves and it backfired

I saw this recently and thought how bad of a money decision it was for Thomas Vanek to turn down the reported $50 million offered by the Islanders

On 4 February 2014, Vanek confirmed that he had turned down a contract extension offer from the Islanders. The contract was reportedly for seven years and $50 million, with Vanek stating that the Islanders move to Barclays Center was one of his primary reasons for leaving the team.

Vanek also wanted to go back to Minnesota and play. He played college hockey there and his wife was from there.

The Sabres already paid him a $hit ton of money so he could afford to be choosy about where he wanted to play.
 
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Another interesting situation is the opposite. Someone who signed a safe deal long term for security but exploded, and regretted it. The NBA one would be Scottie Pippen.
The NHL version will be Nathan Mackinnon. 6.3m has a steal for Colorado. I don't know if they win the stanley cup with out that friendly contract signed by him.
 
Taking my answer in a different direction--

Matt Duchene was cocky and irresponsible, and he ended up burning several bridges and getting jettisoned from several teams. He made plenty of money, but not as much as he could have, and he spent most of his career on weak teams and never found/earned long term stability.
Not sure I get this one. He’s still being paid significant money by Nashville for years to come. He could also definitely be making more than he is in Dallas; He just wants to play there.
 
As someone who doesn’t follow prospects I’ve always been baffled by how anyone thought Zadina had a good shot. It’s one of the most unremarkable parts of his game.

And it’s not just that he couldn’t get a shot off at NHL game speeds. Even when he had all the time in the world the shot was usually poorly placed and nothing special.
This.

Zadina was the epitome of pathetic shooting % - missing half empty nets on many occasions.

I seem to recall a scout commenting about being careful of selecting players who are only known for 1 attribute in a league like the QMJHL.
 
I was at the draft in Edmonton when half the arena was chanting for hometown hero DOAN DOAN DOAN... and a large contingent were cheering for us to draft the other hometown hero Iginla.

Glen Sather went up to the mic and called for Steve Kelly who none of us had heard of.
Nothing could sum up Oilers' inept drafting from about 1983 to 1997 better than this example...
 
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Not sure I get this one. He’s still being paid significant money by Nashville for years to come. He could also definitely be making more than he is in Dallas; He just wants to play there.
Yeah he didn't lose a lot of money, but I'm looking at it from a different angle--I guess more legacy, success, and career turmoil.

He wanted out of Colorado badly enough that he completely burned bridges. He bet that he could go anywhere else and succeed. Ended up in Ottawa and in a terrible situation. Decided that the grass would be greener elsewhere and got traded to Columbus. They wanted to sign him, but he bet that he'd find his place in Nashville. Whatever went down there, he was kicked out. By that time, he's got a terrible reputation and has to accept below market deals in Dallas.

Duchene has/had the on-ice talent to be a core piece on a cup winner. But he's floated around the league and never found his place--despite being one of the proactive about picking where he did/didn't play.
 
The NHL version will be Nathan Mackinnon. 6.3m has a steal for Colorado. I don't know if they win the stanley cup with out that friendly contract signed by him.
The only issue there is that I don't think he regretted that deal.

Although I remember Glencross said he regretted leaving money on the table for the good of the team
 

Labanc still cashed in. Seemed like a handshake deal, take a team friendly 1 year deal to skirt the salary cap and then the extension later despite a down season. So instead of a 5 year, 19.9 mil deal, he got a 1 year for 1 mil deal followed by 4 years for 18.9 million.
And he immediately signed a one year, $775k contract with the Blue Jackets right after.

I'd say that 4yr/18.9M contract was a good bet by Labanc since it was another overpayment by Doug Wilson.

Labanc was a bottom six guy at the peak of his career.
 
Another interesting situation is the opposite. Someone who signed a safe deal long term for security but exploded, and regretted it. The NBA one would be Scottie Pippen.

One random thought that popped into my mind was the handful of guys who signed in the summer of 2004. Many of the big ticket players ended up not signing because of the CBA uncertainty.

Brian Rolston signed a 4 year deal (3.2 mil per year) with Minnesota in the summer of 2004. And then as part of the 2005 CBA negotiation, the players agreed to take a 24% reduction on existing contracts. So Rolston ended up with 3 years x 2.432 mil.

Trying to find a comparable UFA who signed summer of 2005. Off hand, the Devils gave Alexander Mogilny 2 years x 3.5 mil. Glen Murray was the same draft year as Rolston and they were both on the 2003-04 Bruins. Murray got 3 years x 4.125 mil coming out of the lockout. Boston also gave Dave Scatchard 4 years x 2 mil.

So seemingly Rolston would have still been worth the 3.2 mil AAV he originally signed for.
 
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Vanek also wanted to go back to Minnesota and play. He played college hockey there and his wife was from there.

The Sabres already paid him a $hit ton of money so he could afford to be choosy about where he wanted to play.
Vanek also had gambling debt though, so I’m surprised he turned down 50M.
 

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