Just here to feed the hype: http://www.pensionplanpuppets.com/2015/12/10/9886594/can-the-leafs-afford-steven-stamkos
After a great deal of speculation and theoretical GMing:
The Leafs probably have the available capacity to sign Stamkos to a huge contract but doing so is going to mean competing for the cup with a very young team as there won't be much available cap space for free agents.
If Nylander and Marner both earn big dollars in their first RFA period, there could be $25M committed to them plus Stamkos meaning depth players will need to be on entry level contracts or near league minimum (assuming some other prospects like Brown, Johnson, Bracco, Timashov turn into decent players). We'll be into Chicago Blackhawks territory cap-wise so hopefully three Stanley Cups come with it.
It will be tough to keep Kadri and Gardiner long term and moving Phaneuf could be the saving grace. It's also interesting though that the cap crunch probably won't come for several years down the road, giving the Leafs plenty of time to figure out how to navigate the waters.
If we move 2 of Kadri/Gardiner/JvR at this upcoming deadline, then Stamkos is even more of a no-brainer acquisition. I think JvR goes for sure, what with his NMC kicking in next year, and his peak years lining up against our rebuild years. I think Gardiner has the highest chance of staying as he plays a position we don't have much beyond Rielly and potentially Dermott. Kadri will have a crazy thread devoted to his contract conversation near the deadline and draft if he makes it that far.
Moving Bozak/Lupul/Phaneuf would be coups even with very modest returns coming back. We can eat shorter term higher cap hits this year easily.
I think Pridham can make it work. I don't think Stamkos will even be allowed to entertain a hometown discount possibility, as like David Price, the Players Association will be pressuring him to set the market.