Speculation: When do you think the Leafs go "ALL IN"

[LeafsNation75]

I think the Leafs management group is already in full blown “win now” mode (well at least some of thrm - ie Babcock and Lou for sure).

They’ve shown they’re prepared to flip 1st and 2nd round picks for impact players, signed high priced vet free agent in a Marleau and tried to sign other high profile jet in big Joe Thornton.

I’m expecting at this point there’s a Fairly high chance the Leafs flip their 1st and-or prospects for more impact players between now and the draft.

Personally I’d hope they take a more “long/medium term” view of building a contending team once Matthews starts to hit his prime, but I’m not sure if they’ll go down that path.

There is still a difference between signing someone like Marleau as a UFA where all it will cost them is money and cap space, comparing to giving up assets like a 1st round pick which is still something of high value to a young team like the Leafs.

Now if they traded their 1st round pick on the condition that they make the playoffs it's one thing. However to still trade it without that condition is another thing, even if the Leafs have a 99.7% chance at making the playoffs this season.

If they traded it at the draft for a high impact roster player for next season at least we would know what specific spot in the 1st round they would be giving up. Like when Calgary traded their 1st round pick in 2015 at the draft for Dougie Hamilton.

 

[Albert Iafrate]

I think the organization can't add the "all in" pieces until the big 3 are signed, and when they know if they need to re-sign Gardiner, or if Dermott replaces him. Nylander will hopefully be signed this off season, and Matthews and Marner will be re-signed shortly after. Then it will be..."can Dermott fill Gardiner's spot". If he can (which it looks like he can) you've got 3 of your top 4 D locked in. That means that the off season to watch is the summer of 2019 when guys like Doughty, Karlsson, OEL, Seguin, and Kucherov could be free agents. Those are guys you sign or trade for to go "all in". That summer we will truly know how much space we have to grab one or two of those guys. Long story-short: 2019/2020 is the season we "go for it" IMO.