Under the leadership of Kyle Dubas, the Toronto Maple Leafs’ roster is likely to always remain a work in progress.

There will always be a market inefficiency to tap into; a weakness to address; a missing piece to acquire. It’s the natural path for a forward-thinking team. Operating within a league that requires constant ascension, Dubas is a GM who rarely finds happiness in the concept of “good enough”. And, at the moment, that’s more or less what these Leafs project to be.

Could another dip into the free agent pool be enough to change that? Good question! Let’s take a quick look through the remainder of the 2019 UFA class and find out.

Dion Phaneuf

Position: LHD

Age (as of October 2nd, 2019): 34

2018-19 Cap Hit: $7,000,000

2019-19 Statline: 1 goal, 5 assists for 6 points in 67 games

Nope. Absolutely not. Not even if there’s a FIRE.

Dion Phaneuf is not a good enough defenceman to contribute at the NHL level – at least, not anymore. Even when ignoring the age factor (Phaneuf is set to turn 35 in April) the former and most recent Leaf captain is also coming off a season in which he watched a good chunk of his games from the press box as a healthy scratch.

I’m just going to repeat that last part for emphasis. Dion Phaneuf was a healthy scratch on the Los Angeles Kings. Like, last year. That’s honestly pretty impressive. The 2018-19 Kings were a team in such dire need of defensive help that they viewed Derek Forbort logging 20 minutes per night as their best available option, and even they took a glance at Phaneuf and thought, “Eh, we’re good”.

I don’t care if he signs for league minimum; I don’t care if he enters training camp “in the best shape of his life”; I don’t even care if he magically changes shooting hands. Spare me.

Phaneuf is a good guy. That much is not up for debate. At each stop in his career, Phaneuf has consistently made an effort to involve himself in charitable endeavours while shying away from outside attention. That’s what true charity looks like.

Listen, I’d call Phaneuf if I needed help moving. I’d call someone else to improve my hockey team.

And when it comes to the nostalgia a Phaneuf return would conjure back up, Kylo Ren said it best:

Patrick Marleau

Position: C/LW

Age (as of October 2nd, 2019): 40

2018-19 Cap Hit: $

2018-19 Statline: 16 goals, 21 assists, 37 points in 82 games

Gonna be another “no” from me, dawg.

The adopted father of the Maple Leafs will not be pulling a Brooks Orpik and come strolling back into town on the cheap, regardless of much you want him to. Mom and Dad got a divorce. You can’t “Parent Trap” them back together. Relationships don’t work that way. It’s time you learned the truth.

(Hilarious) jokes aside, the Leafs and Marleau seem entirely content with the joint decision to go their separate ways at this year’s draft. Marleau’s family moved to the opposite end of the continent (seemingly for good) in early June following his trade request, and the Maple Leafs happily granted it to him soon after by shipping Marleau to Carolina – where he then took a hard pass on joining the Jerk Squad™ and became a UFA.

Out on the open market, Marleau’s sole focus for next season is to reportedly latch on with a team based out of Southern California, which severely limits his options. Maybe a second tour in San Jose is in the cards; maybe he heads to Los Angeles. Either way, Toronto doesn’t fit that bill.

The Marleau Era was a terrifically fun (and meme-worthy) ride; a necessary stepping stone for the progression of the Leafs’ young core. Fans will never forget it. But it’s over. Farewell, sweet prince.

Derick Brassard

Position: Centre

Age (as of October 2nd, 2019): 32

2018-19 Cap Hit: $5,000,000

2018-19 Statline: 14 goals, 9 assists for 23 points in 70 games

What the hell happened to Derick Brassard?

This guy was rattling off 40- to 50-point seasons with the ease of a mid-Autumn stroll through a farmer’s market less than 24 months ago, playing an integral role for the Senators during their miraculous (and, in hindsight, hilarious) run to the 2016-17 Eastern Conference Final before coming to be viewed as one of the trading market’s top assets at the following deadline.

Life comes at you fast, I guess.

Fast forward to July 14th, 2019, and Brassard floats aimlessly in UFA purgatory. As his NHL stock wilts in the gloomy aftermath of a season in which he barely cracked the 20-point barrier, fell to the fourth line, and saw himself get traded by two different teams, Brassard is in dire need a fresh start. Perhaps that could make him an intriguing depth target for the Leafs.

The concept isn’t all that unreasonable, either. Brassard certainly wouldn’t be the first formerly-effective veteran to seek out a career revival with the Maple Leafs. Just ask Tyler Ennis how his dip in the Fountain of Youth went last year.

But whereas Ennis joined a Leafs team that was, at the time, scouring the market for his particular archetype (cheap, skilled wingers), Brassard is not as lucky. He’s a depth centre – one who would be vying for a spot on a team that just spent the early stages of their summer locking up as many of them as possible.

Toronto’s bottom-six is now padded down the middle with new arrivals in Jason Spezza, Nick Shore and Alexander Kerfoot, bolstering a depth chart that already features centres Nic Petan and Frederik Gauthier.

Where would Brassard even slot within that group? And, perhaps most importantly, would he offer an upgrade over any whose last name doesn’t rhyme with “Boatier”?

Honestly, I don’t know. Ever since that magical run with the Senators, Brassard’s ability to drive possession at 5v5 has hit a cliff with such force it would make Wiley E. Coyote blush (53.9% CF/60 in 2016-17, 50.6% in 17-18, 45.1% in 18-19, per HockeyReference).

Some of that drop can be attributed to a constant change in address; some of it to an athlete’s natural post-age-30 decline. But that’s a steep drop nonetheless; enough to make any team think twice before committing to Brassard even for just one year.

At this point, Brassard’s only avenue to Leafs’ training camp is likely as a late-August PTO.

Andrew MacDonald

Position: LHD

Age (as of October 2nd, 2019): 33

2018-19 Cap Hit: $5,000,000 (lmao)

2018-19 Statline: 0 goals, 9 assists for 9 points in 47 games

C’mon, man.

We’ll continue our search through the bargain bin later this week.