I actually said a very similar thing when he originally signed his current deal, I said it was too much and he needed to take a bigger discount if he wanted cup wins instead of just having money. I still stand by that point. I get Drai and Bouch going after the paycheck, they haven't made nearly as much over their careers, and don't make $5-7 M per year in endorsements like McDavid does. Dari/Bouch will go for the bank, and I get it, but McDavid is another animal altogether. McDavid will have already made about $150M in earnings by the time his next contract kicks in, and even with a very friendly team contract, he will make another ~$150-175 M in salary/endorsement earnings by the time he retires. So even if he signs a very friendly deal, he'll have made about $300-325 M in career earnings. I know 28 year old people generally don't think like this, so it might be asking too much, but when he is on his death bed, he isn't going to think back and be upset about not making another $25 M, he'll think back and be upset about not winning a cup. That is how he (and really all of us I would argue) should think about big life decisions.
If McDavid is serious about winning a cup, wherever he signs (us or another team) he will sign a very team friendly deal.