Can the Toronto Maple Leafs not win for losing?

How so? They got rid of a boat anchor contract without retaining salary and got a decent prospect and a draft pick in the process. They have cap space (how they use it and how effectively they use it is yet to be determined and I'd be lying if I said I wasn't concerned). They put Phaneuf with Gardiner (his WOWY with Gardiner underlines how good Gardiner is) to prop up his possession numbers.

They were never going to be that good this year- they're respectable which is about all I hoped for (although watching Montreal implode is hilarious).

They're a better possession team this year and they're more structured and they're not icing 2 facepunchers.

Baby steps.

They have a ton of draft picks this year.

Look- a year ago, if you'd have told me that Nonis would be a memory and that Phaneuf and Clarkson would be gone without retaining salary, and you'd have Mike Babcock coaching I'd have thought you were crazy. They're not there yet (I'd say 2 years away from being a playoff team), but they're doing an actual, legit rebuild. Acquire a boatload of picks and prospects, draft for elite high end talent.

Yes, it's going to take time.

They haven't won in decades.

Yes, they can and will not win for losing.

they can't get out of their own way

nope and great idea to trade away defence for more offence