Trade grades: Leafs go all-in with O'Reilly, decisive Blues collect picks

Kyle Dubas isn't messing around. Not this year.

Late Friday, the Toronto Maple Leafs general manager acquired forwards Ryan O'Reilly and Noel Acciari and prospect Josh Pillar as part of a massive three-team swap. In return, the St. Louis Blues received a 2023 first-round pick, a 2024 second-rounder, a 2023 third-rounder, and prospects Adam Gaudette and Mikhail Abramov, while the Minnesota Wild received a 2025 fourth-rounder.

O'Reilly's $7.5-million salary and cap hit will be split between the Blues (50%), Wild (25%), and Leafs (25%). He's a $1.875-million player on Toronto's books.

Let's dig into the three perspectives of the trade.

Maple Leafs' side of the deal

Let's start with the lineup: the Maple Leafs now have either a lethal 1-2-3 punch at center - with O'Reilly joining Auston Matthews and John Tavares - or a deadly two-way second line of Tavares between O'Reilly and Mitch Marner.

Those are the most obvious and alluring scenarios for Leafs coach Sheldon Keefe after watching Dubas sacrifice four draft picks and two minor-leaguers to acquire O'Reilly (and Acciari, of course). This is an all-in move the fan base should welcome with open arms. It addresses a need (impact top-six forward), injects depth (Acciari), and doesn't subtract a player from the roster.

The cost to reel in O'Reilly, a 32-year-old pending unrestricted free agent, was unquestionably steep. But the whole point of pro sports is to chase championships. On paper, the Leafs possess a core capable of long playoff runs. They've underachieved, losing six straight series, so stacking the supporting cast with as much talent as possible is a perfectly logical strategy.

Dubas, who just last week said he'd be "hard-pressed" to part with Toronto's 2023 first-rounder and/or top prospect Matthew Knies, clearly doesn't want to leave anything to chance this season. The GM is on an expiring contract, the local market has grown increasingly impatient, and Matthews and William Nylander are 17 months from potentially testing unrestricted free agency.

In other words, if there was ever a time to throw caution to the wind, it's now - even with the juggernaut Boston Bruins and the recent champion Tampa Bay Lightning in the same division. The window to contend won't be open forever.

O'Reilly won the Selke Trophy, Conn Smythe Trophy, and Stanley Cup in 2018-19. He's one of the top defensive centers of his generation and a clutch performer. However, his output this year - counting stats and underlying numbers - isn't pretty. For the Blues, he recorded 19 points in 40 games and posted a five-on-five expected goals rate around 50% - not bad, but not up to his lofty standards. (O'Reilly missed the start of 2023 with a broken foot.)

I'm tempted to give the Leafs an "A" grade, as I applaud them for being aggressive and landing a notable name. But I'll dock them a bit because of the quality and quantity of assets surrendered to net O'Reilly. Two things can be true: Toronto picked up a key piece, and Toronto paid a hefty price.

Grade: B+

Blues' side of the deal

First Vladimir Tarasenko. Now O'Reilly. The retooling continues in St. Louis.

The headline with the Blues is that they now own three first-round picks for the upcoming draft. The 2023 crop of players is widely believed to be one of the strongest in recent memory. GM Doug Armstrong, then, deserves props for being decisive and efficient. Only so many 2023 firsts will move ahead of the deadline, and Armstrong scooped up two over the span of eight days.

Considering O'Reilly is having a down year, team and player weren't working on an extension, and the Blues have fallen way out of the playoff hunt in the West, this is an impressive haul. Gaudette and Abramov don't have high ceilings - it's possible neither becomes an everyday NHLer - but the picks are incredibly valuable to a club trying to transition into a new era fairly quickly.

Armstrong probably isn't done wheeling and dealing. Forward Ivan Barbashev, another pending UFA, will likely be dealt over the next two weeks, and he could easily fetch a second-rounder. Backup goalie Thomas Greiss will surely garner interest, too. And there's a chance Armstrong shops one of his many defensemen with term - perhaps Colton Parayko or maybe Torey Krug.

Construction is well underway in Blues land. The early returns are promising.

Grade: A

Wild's side of the deal

Will Wild legend O'Reilly get the video tribute treatment in Minnesota?

Jokes aside, Bill Guerin did something Friday that more GMs in the NHL should do - he played third-party broker in exchange for draft capital. Technically, O'Reilly was traded from the Blues to the Wild, then from the Wild to the Leafs, in order for Minnesota to retain 25% of the veteran's salary.

The Wild received a mid-rounder for their troubles (they have about $10 million in cap space, so no biggie), and sending Pillar to the Leafs is an afterthought.

There's no need to overanalyze the Wild's perspective. They acquired a pick for a low-downside favor. Could the pick have been higher? Maybe, sure.

While the Blues made out best, this is an extremely rare win-win-win trade.

Grade: B+

John Matisz is theScore's senior NHL writer. Follow John on Twitter (@MatiszJohn) or contact him via email ([email protected]).