Landeskog was a UFA heading into the expansion draft. Had they signed him before it took place, they would have had to protect him and lost a bigger asset to the Kraken.
Colorado had some incentive in that regard to delay the signing until after the expansion draft.
Stamkos had no risk, high reward by waiting until the UFA courting period occurred because he could then find out really if the 8th year was worth it to him or not while putting pressure on Yzerman with cold hard facts about who was serious about acquiring him.
Calgary has no incentive to delay the signing like Colorado, in fact the uncertainty likely caused issues as they headed into the draft and did not know which road they were taking. Gaudreau can play hardball but it's not like something changes between today or tomorrow in terms of external pressure (at least not outside of illegal tampering).
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