Never give a guy turning 29 term, especially when he has back injury history. That is monumentally a bad idea. I'd be surprised if Gardiner plays beyond 33 and I bet he becomes a healthy scratch by 31. Without speed he is nothing and he looked slow last year due to his back.

why would you keep a team together that has lost in the 1st round the past 3 years.

its time to move on from some guys to improve the defence

I get that, but I also think they will get good value for 5 years of this contract. 34 year old Gardiner will be a top 6 LD. Front load the contract with bonuses, ship him out for the last half. If he's willing to give you a discount (which it sounds like he is), then you use that to your advantage

1) They have 5 guys who are <22 years old. They will be much better this year.
2) They were still a top 5 team last year, don't over react because you lost to the eventual Eastern champs. Definitely improve (i.e shipping out Marleau, Zaitsev), but don't over react
3) What D are available on the market right now? I'd rather spend the money on Gardiner who's apparently willing to come in cheaper than his value

you're entitled to your opinion. Im fine with keeping gardiner, but we wont get him for that cheap. I think moving on from kadri is the right move, and brown for a 3rd is terrible asset management.

You think way too much of Gardiner. Sandin will be better than him in 2 seasons. Muzzin is already better and Dermott likely is as well. Gardiner's time in TO is over.