Can Maple Leafs plummet to bottom five and still keep their first-round pick?

TORONTO — When the Toronto Maple Leafs traded their 2026 first-round pick (along with Fraser Minten and an additional fourth-rounder) at last year’s trade deadline to the Boston Bruins for Brandon Carlo, you didn’t have to squint to at least see what they were thinking.

That was, “It’s a lot but it’s a top-four right-handed D, he’s only 28, he has three seasons of term left, and they Bruins will retain $615,000 per season.” This was in a year where the Leafs were winning the Atlantic Division, considered themselves real Cup contenders, and most fans were clamouring for some impact adds.

Whether they identified the right adds that deadline or not — and I think there’s some real strong opinions out there on that very point — that’s another story. But you can at least see their thought process.

None of the above is to defend what was clearly a massive overpay, but that’s what happens when you leave your Christmas shopping until Christmas Eve. It’s just worth remembering that there was context beyond “Carlo for Minten and a first,” as the deal is mostly portrayed now, invisible things like “salary retention” and “years of term” that cost something too.

But what was really indefensible about the whole thing, aside from moving Minten at all, was getting the pick only “top-five protected.” 

The whole thing hurts, but this is salt in the wound.

Without knowing how they exactly settled on “top five,” it feels fairly certain this part wasn’t given as much thought as the rest of it, considering their place in the standings at the time. It always bothers me that all these picks are protected by the big, round numbers, fives and 10s, like teams just toss out a ballpark-convenient number rather than legitimately working to insure against disaster. If the Leafs could’ve gotten this to not even top-10 protected, but to top-nine, top-eight, seven, something better, they’d have a viable path to still pick high in the first round this upcoming draft.

But with how things currently stand, with it being top-five protected, they’re at a crossroads of a different sort. Instead of deciding whether they’re all-in on playoffs, and whether they should add depth help or not — as it was as recently as 10 days ago — it’s time to decide whether they should get all the way out on the business of winning for a sec and try to drop into that bottom five.

It won’t be easy — they’ve still got legit talent — but it’s also not impossible. 

The way the Leafs bottomed out in 2015-16 springs to mind, just a one-year plummet followed by an immediate resurgence. Could they muster an even shorter version of that again?

First, let’s talk about how viable the drop to bottom-five really is. As things stand, here’s how far they are from the basement:

If they could drop to where the Rangers are, that coveted 28^th spot, they’d get to keep their pick, and they’d immediately be picking an impact player. According to Sportsnet’s Jason Bukala, who joined us on Real Kyper & Bourne on Thursday, the tiering of talent in the upcoming draft means anyone picking in the top six is likely getting a difference-maker. Lord knows the Leafs could use that if they are, in fact, attempting a quick “retool” and a turnaround.

That’s not to say they’d even keep the kid they drafted there, though they probably would. But with a star name apparently available for the right price — I’m thinking here specifically of Robert Thomas from St. Louis — perhaps a top-five pick is something they could spin the Blues’ way to get immediately, meaningfully better.

Now, the other element here, before we go on to what would have to happen, is that finishing bottom-five does not guarantee that you get a top-five pick because of the way the draft lottery works.

Here’s what you need to know about the lottery: 

Lottery balls determine who picks No. 1 and who picks No. 2. That’s all they determine, just two spots. After they do that, it’s all just reverse standings order from there.

They have 14 lottery balls create 1,001 possible four-number combinations for the lottery, and each team is assigned a share of those four-number combos, based on where they finished. 

Odds of picking 1^st overall:

Dead last: 18.5%

Second last: 13.5%

Third last: 11.5%

Fourth last: 9.5%

Fifth last: 8.5%

And so on down, 7.5%, 6.5%, 6.0%, 5.0%, 3.5%, 3.0%, 2.5%, 2.0%, 1.5%, 0.5%, 0.5%.

So, the top five have combined odds of winning the lottery of 61.5 per cent, meaning it’s more likely than not that the top pick comes from a team in the top five, which would leave fifth-to-last team picking in the top five. But then another team gets picked for second, and it’s just no guarantee you don’t get bumped. Mathematically, you probably do. 

Just ask the Detroit Red Wings, who have dropped five times thanks to the lottery from 2017 until now, including finishing last and picking fourth in 2020.

Here are the last 10 fifth-last finishers, and where they picked in the ensuing NHL Draft, all of whom had an 8.5 per cent chance of getting the top pick:

2016: Flames, 6^th

2017: Devils, 1^st

2018: Red Wings, 6^th

2019: Sabres, 7^th

2020: Ducks, 6^th

2021: Blue Jackets, 5^th

2022: Devils, 2^nd

2023: Canadiens, 5^th

2024: Canadiens, 5^th

2025: Bruins, 7^th

Finishing fifth-worst allowed teams to pick in the top five half the time.

Essentially what I’m saying is, the Leafs could fall to fifth-last and get lucky, or they could get still get bumped out and hand the Bruins the sixth-overall pick. It’s a matter of slim percentages and fortune. 

The only guarantee of picking in the top five is by finishing third-last, and that’s a much farther fall. (Teams that finished fourth-last over the past 10 years picked in the top five seven times.)

There’s also the Hail Mary hope that they could see their numbers come up as the Islanders did and pick first or second overall, odds that would be increased by losing down the stretch. (Fun fact, no team can move up more than 10 spots, so if you finish 12th, best you could pick if you won the lottery is third. The Islanders pulled off the dream last year, finishing 10th-last, having a 3.5 per cent chance to get the first-overall pick, and getting flat-out lucky.)

And so, with all this in mind — holy smokes, Bourne, get to the point — is it even doable?

The last three years, the team in 28th has finished with 76 points, 76 points and 68 points. The Leafs currently have 57 points with 28 games left, which would mean they’d need a record of 9-18-1 to finish with 76 points, which honestly may not even be bad enough. That might get you fifth-last.

And yet, they’re coming off a stretch where they just went 0-5-1, looking awful in the process. They’ve given up an average of five goals per game over those six games, and are dead last in the league in goals against. It’s been rough, and the goaltending is patching over roughly zero mistakes.

The Leafs have got one of the 10 hardest schedules remaining in the league, which includes 18 of their final 28 games on the road. Only one team in the NHL has fewer road wins than the Leafs this season (St. Louis), which is partially games-played-related, but mostly related to games played poorly.

They could very easily take the weight off whatever’s been ailing Matthew Knies and let him rest. They could let William Nylander work his injuries back to full health by letting him sit out a lot longer. Half the D-corps has been limping around if you want to give games off.

You could play more Jacob Quillan, you could give a host of other Toronto Marlies an NHL taste-test (a la 2015-16, when just about every Marlie got a few games), and you could let Artur Akthyamov get some run in the NHL. 

And, of course, you could sell off assets for some valuable returns, as I don’t think your team would be better once you strip Bobby McMann or Oliver Ekman-Larsson or Scott Laughton from the roster. Actually, you’ll definitely be worse in the short term. I wouldn’t want to trade all those guys, I’m just saying, there are names you’re going to have to consider, from Morgan Rielly to Max Domi and all the way on down.

The reality is, the end of the regular season is only 10 weeks away, and a lot of this season has been spent in pursuit of winning. It’s not that far from here to make the pivot and try to develop some young players while recouping assets in the process of tanking. It’s worth trying, if you’re serious about a reload.

Look, I hate advocating for losing, I wish it were never this way in the NHL, but that’s just the perverse nature of the NHL’s draft structure, and so you have to play within its confines. 

As the Leafs consider what steps to take next, I don’t know that this will be the route they choose. But with all the facts at their disposal, it’s at very least a path they have to consider.

The bottom has fallen out, and pain is coming. They might as well take that medicine and hope for as prompt a recovery as possible, which would be aided by grabbing one of the top talents in this summer’s NHL Draft.