NHL insider Chris Johnston provided an update on Monday on his podcast, The CJ Show. Johnston said on the show, "I'm not certain he will sign before training camp."
Not exactly the news Leaf fans want to hear, but it was somewhat expected given Sandin's agent's comments above. Gross is also the agent for William Nylander, who notoriously held out from signing his current deal until the last possible moment in 2018. Dubas could be headed down the same path with Sandin and the longer into the season Sandin remains unsigned the more issues it will cause for the Leafs and their cap crunch.
For reference, say Sandin signs for $2M per season on December first. but he is being paid $3M in actual dollars. If my math is correct, and say there are 130 days left in the season, his cap hit would actually be $3.9M for this season instead of only $2M if he signed a 3-year, $6M deal. As with all teams at the start of the season, the Leafs will be cap compliant, but should Sandin sign on December 1st and if there are no injuries on the Leafs' roster, they will have to find a way to fit almost $4M under the cap. That means trades and possibly waivers and it could very well cost the Leafs a quality roster player or two.
Get your popcorn out and find a comfy seat because by the sounds of it, we're in for a very long negotiation. I know nobody is looking forward to it, but unfortunately that appears to be the reality.