Grading John Chayka's First Maple Leafs Offseason Before the Draft Even Starts

John Chayka's Maple Leafs offseason deserves a hard look

The draft hasn't started, free agency is still more than a week away, and John Chayka's Maple Leafs offseason already has more moving parts than most full summers in Toronto. Since taking over as general manager in May, Chayka has hired a head coach, traded a goalie, signed a defenceman to an eight-year deal, told the league Matthew Knies isn't going anywhere, and put Morgan Rielly on the market. That is a lot of decisive action from a first-year GM — and decisive isn't the same as correct. With the No. 1 overall pick about to land, it's a fair moment to grade the work so far.

This is LeafsLurker, so we'll be direct: some of these moves are smart, one is an overpay the team can live with, and the most important one hasn't actually happened yet. Here's the report card.

The Joseph Woll trade: B+

Chayka's first real swing was moving Joseph Woll and Simon Benoit to Philadelphia for Samuel Ersson, Emil Andrae and a third-round pick. The grade here is high because of the philosophy behind it. Toronto turned a goalie it could afford to lose — given the emergence of Dennis Hildeby and Artur Akhtyamov behind Anthony Stolarz — into a younger, mobile, left-shot defenceman with upside in Andrae, plus a pick and goaltending insurance.

The risk is obvious: if the prospect goalies aren't ready, dealing a proven NHL netminder will look like overconfidence, a tension we explored in our breakdown of the Woll trade as Chayka's first big swing. But betting on internal development instead of hoarding depth is exactly the kind of decision the old regime rarely made. Bold, defensible, and only an A away because the return is good rather than spectacular.

The Darren Raddysh sign-and-trade: C+

This is the one that makes you wince a little. Chayka acquired Darren Raddysh from Tampa Bay in a sign-and-trade for a fifth-round pick and immediately handed him a reported eight-year contract worth around $8.5 million per season. Raddysh is a genuinely useful, puck-moving right-shot defenceman, and the Leafs needed exactly that — mobility on the back end was the team's stated priority all spring.

The problem is the term and the dollars. Eight years and $8.5 million is top-pairing money and top-pairing commitment for a defenceman who has been a very good complementary piece, not a driver. In a rising-cap world it's survivable, and we said as much in our analysis of the Raddysh sign-and-trade — but Chayka went higher and longer than the market required. You don't fail a team for addressing its biggest need. You do dock it for the price.

The Jim Hiller hire: B

After firing Craig Berube and conducting a coaching search that touched dozens of candidates, Chayka landed on Jim Hiller — a surprise to a fan base that had spent weeks debating bigger names. The grade reflects both the merit and the uncertainty. Hiller is an experienced, well-regarded bench voice, and the process was thorough rather than impulsive.

But it's a bet on fit over flash, and bets like that take a season to grade properly. We laid out the reasoning in our look at why Chayka chose Hiller, and the short version is that this is a coach hired to install structure, not to sell tickets. That's the right priority for this roster. The B is an incomplete in disguise — ask again in April.

The Matthew Knies stance: A-

Sometimes the best move is the one you don't make. Chayka was blunt that trading Matthew Knies is "not probable," describing it as a tough bar to clear, even as rival teams circled a 22-year-old power forward signed through 2030-31. Toronto nearly dealt Knies to Montreal at the deadline under the previous regime; Chayka effectively closed that door.

Holding a cost-controlled, ascending winger who wants to be in Toronto is simply good asset management, and we agreed in our piece on why a Knies trade isn't probable — and shouldn't be. The near-A reflects how easy it would have been to cash Knies in for a quick fix. Chayka didn't, and that restraint matters.

The other half of the Knies grade is what it signals. A GM who keeps his best young forward despite a steady drumbeat of trade interest is telling the room — and the captain — that this isn't a fire sale. That message has value beyond the player himself, and it's part of why the broader retool has read as coherent rather than panicked.

The Morgan Rielly situation: Incomplete

The biggest item on the board is unresolved. Rielly has given Chayka a list of teams he'd accept a trade to — his full no-movement clause gives him that control — and the market has reportedly narrowed toward Western Conference clubs, with Anaheim the latest name in the mix. We tracked the latest in our report that Rielly's list now includes the Ducks.

You can't grade a trade that hasn't closed. What you can say is that managing a franchise icon's exit without torching the return or the relationship is the hardest thing Chayka has on his plate, and the draft is the obvious stage for it. The return he extracts — and whether he eats salary to get it — will define this summer more than any move he's already made.

McKenna and the No. 1 pick: A (pending)

The easiest grade on the board. Toronto won the draft lottery, holds the No. 1 overall pick, and is widely expected to select Penn State phenom Gavin McKenna on June 26. McKenna is the consensus best player in the class — a dynamic, Whitehorse-born winger who put up 51 points in 35 NCAA games — and there is no defensible case for taking anyone else. We broke down exactly what Toronto is getting in our McKenna scouting report.

The only way Chayka fails this one is by overthinking it, and nothing he's said suggests he will. Getting the obvious pick right is the floor, not the ceiling — but for a franchise that has rarely picked this high, simply not fumbling a generational talent is worth the top mark. You can follow the full slate of selections on our draft page.

The overall grade: B+

Add it up and Chayka's first Maple Leafs offseason earns a B+ heading into the draft. He has been aggressive without being reckless, addressed the team's stated needs in net and on the blue line, kept the young player worth keeping, and is poised to add a franchise cornerstone at No. 1. The Raddysh term is the one clear demerit, and the Rielly trade is the swing that could lift the whole grade — or sink it — once it lands.

What stands out most is coherence. For years, Toronto's offseasons felt like a collection of reactions. This one has a thesis: get faster and more mobile on defence, trust the kids in net, protect the young core, and build around a No. 1 pick. You can quibble with the price tags. You can't say you don't know the plan. For a first-year GM walking into a market this loud, that clarity is the most encouraging grade of all. Track every commitment as it lands on our contracts page.