If you don't look at the entire picture, including what that contract will look like at the end, your not a very good GM.
Now a GM may look at a contract, believe it may be bad at the end and still say "screw it" I want the player. It happens no doubt. Especially for guys who are franchise pillars. I get why some GM's do it. I get why San Jose gave Hertl the contract they did.
But doesn't mean I think it's a good contract or a contract for they type of player I'd be willing to overlook the term and potential for it to be a future buy out. I guess at the end of the day, I don't believe Tomas Hertl to be good enough of a player to overlook how bad his contract will impact my franchise 4-5-6 years down the road. That's my opinion on the player and I am entitled to it. Even if some disagree.
Injury or not he was still slowing down as he got older.