TL;DR: This is a very rough estimation, but I think that as long as the team doesn't commit an additional $12million into the 2019-2020 season, we will be able to comfortably sign all of Nylander, Matthews, Marner and, if we want, Gardiner, Kapanen and Dermott as well to new contracts.

With next year being Nylander's contract year and July 1st, 2018 marking the first day both Matthews and Marner can sign their first post-ELC contracts, I don't think it's too early to speculate on the term/value of those contracts. I haven't done any research to make worthwhile speculations, but I do want to talk a little about the Leafs cap situation.

I have read so many times Leafs fans saying that we can't sign 'free agent X' because we need to save money for the Big 3 contracts. To these people I genuinely ask, how much money do you think we need to re-sign all three?

By the end of this season we spent almost all of the $73m cap. The cap is expected to rise to about $76 next season, giving $3m more to work with. We also have an additional $11.3m of 'free money' coming onto our books by way of the Greening, Laich, Michalek and Robidas contracts ending.

So that's $14m of cap space before we talk roster guys. Our only RFAs to sign are Brown and Hyman (their current $1.6m combined will turn into about $6.1m, or a $4.5 increase in cap hit). So that leaves the team with ~$9.5m after RFA signings.

A portion of that money will be used to re-sign/replace Boyle($2m), Hunwick($1.2m), Polak($2.25m) and McBackup($0.8m). On July 1st, those four are off the books, adding $6.25m to our bank, putting our cap space back at around $15.5m, and (barring trades or external signings) a roster looking like:

Hyman - Matthews - Nylander

JvR - Bozak - Marner

Komorov - Kadri - Brown

Martin - ( ____ ) - Soshnikov

extras: Fehr (2), Leivo(0.6), Smith(0.65)

Rielly - ( ____ )

Gardiner - Zaitsev

( ____ ) - Carrick

extras: Marchenko(1.45), Marincin(1.25)

Andersen

( ____ )

Note: The nice thing about each of the 'extras' is that their contracts end at the end of next year (combined $6m).

The Leafs have a lot of money to work with and not a lot of holes to fill. Plus, a couple of cheap AHLers could make the big squad full-time next season in Kapanen(0.86) and Dermott(0.9).

I won't speculate beyond the 2017-2018 season, but it is worth noting that Nylander will then be due for his raise. This should not pose any problem as we have some more 'free money' coming off the books in Lupul(5.25) and Gleason(1.3). Not to mention the salary cap should increase again. And if they are still on the team by then, JvR(4.25) and Bozak(4.2) will also be off the books (in addition to the 'extras' $6m from the above lineup). So Nylander can be signed easily even if we spend to the cap again next year.

The important thing is that the Leafs are careful with how much money is invested into the 2019-2020 season. Following the 2018-2019 season, when AM34 and MM16 need new contracts, we have no 'free money' coming off the books. In fact, the only other contracts set to expire that year are Gardiner (if his play continues to improve he will need a big raise on his $4.05), Kapanen (post-ELC deal raise), and Dermott (post-ELC deal raise). So any player we sign/trade for as of now with 3 years on their contract will dig into the money we have to spend on Matthews and Marner (and Gardiner, etc.).

While the Leafs might need ~$20million to sign the big 3, we will have $15m of cap space going into next season after signing Brown Hyman, and another $6.5 coming off the books after next season just from buried contracts, LTIR, etc. With the Bozak, JvR, and Komorov contracts on the way out (combined $11.4m), we could have more cap room if we replace them internally for cheaper. Not to mention the salary cap can increase each year. So as long as we don't sign two guys at 7x7, Lou and company should have lots of cap flexibility and pieces to play with. I think any external contracts we sign this offseason, especially of high value, should be for 1-2 years. This allows the team to be a lot more active during the 2018 and 2019 free agency periods.

Please let me know your speculations, or if I messed up any numbers. C-Friendly was my main source.

Edit: Actual cap space before any signings is $12M and carryover of $4.675M in bonuses.