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Originally Posted by Vinny01
Don’t see any reason why Tkachuk would consider entertaining that.
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It brings him to UFA as a 29 year old. At that time he would presumably be the most sought after free agent that year still in his prime. There are currently 11 skaters with a cap-hit over 10M. Three of them were signed as 28 or 29 year olds (Karlsson, Doughty, Kopitar). None of them are particularly living up to their contracts in terms of being top 10 players in the league (in part due to injuries). It's quite clear teams are willing to pay those 29 year olds as though they don't have a major chance of regression by the end of the contract. And these were all signed by their current team without even making UFA.
Sign a 5 year deal, all at "prime" value. Then sign a 7 or 8 year deal, again all at "prime" value that brings him to retirement at 36 or 37. That's probably nearing the best way to maximize his career earnings while mitigating risk.
He could try to become a UFA as early as possible, but now he's a 25 year old with teams wanting him for 7 years bringing him to 32/33 and could be regressing like we see with a lot of players. Like Toews even and the chance of that big contract is less likely. Same results if he signs for 8 years.
He could also sign a series of one year contracts of course, or a 1 year deal then a 4 year deal, to again get to UFA as a 29 year old but it does increase risk if an injury or bad season happens during that 1 year.