Late in the evening on Friday night, Kyle Dubas made his mark on the 2023 deadline with a blockbuster deal, acquiring Ryan O’Reilly and Noel Acciari from the St. Louis Blues in exchange for a whole bunch of draft picks.

It’s a hefty price for a pair of (as of today) rentals, but no one can argue that the Leafs didn’t make the forward group significantly better by effectively filling two obvious needs — a 3C who can also play top-six LW, plus a gritty bottom-six right-shot option with PK utility and some finishing ability.

Let’s dive in.

Ryan O’Reilly’s profile

Ryan O'Reilly, Vladimir Tarasenko, St. Louis Blues
Photo: Jeff Curry-USA TODAY Sports

O’Reilly, a premiere forward in this league for many years, has been in the midst of a down year by his standards, but he still has a lot to offer.

A native of Clinton, ON who developed in the OHL with the Erie Otters, O’Reilly was drafted 33rd overall in 2009 by the Colorado Avalanche and debuted in the NHL at age 18 in the 2009-10 season.

By his third year in the league, he was already receiving Selke votes as a superb defensive center. His offensive breakout campaign — 28 goals and 64 points — came on the surprising 2013-14 Colorado team that won the Central Division. He placed sixth in the Selke voting that year and also won the Lady Byng after taking an astonishing two penalty minutes that season. Reilly had earned his distinction as one of the top two-way centermen in the league.

Colorado entered a re-tool in the mid-2010s and O’Reilly was dealt to Buffalo in the summer of 2015 for JT Compher, Mikhail Grigorenko, Nikita Zadorov, and a second-rounder. With the Sabres, O’Reilly played as a 2C behind Jack Eichel on a still-bad Buffalo squad, scoring in the 60-point range, coming close to another Byng win in 2018, and finishing on the periphery of Selke voting.

Buffalo wasn’t anywhere close to contention in the summer of 2018, and so O’Reilly was traded to St. Louis in what has turned out to be one of the great win-win deals in recent history. He was shipped to the Blues for Tage Thompson and a first-round pick, among other pieces.

In St. Louis, O’Reilly hit his peak. His 2018-19 season was an all-timer: 28 goals and 77 points, playing 20:46 per night and taking just 12 penalty minutes the whole regular season while playing dominant defense. He finally won the Selke, was the runner-up to the Lady Byng, and in the playoffs, he posted 8-15-23 in 26 games. He led the team in playoff points and served as the team’s number-one center as the Blues won the Stanley Cup and ended a Cup drought spanning back to their entrance into the league in 1967 (hmm… anything familiar about that year?).

O’Reilly was the best player on the Blues during those playoffs and the media recognized him with the Conn Smythe Trophy honours as playoff MVP.

Over the past three completed seasons since then, O’Reilly has remained a productive player, scoring 21 goals and 58 points last year, but this year has been more of a challenge, which leads us to the now.

This season’s stat line is disappointing: 12 goals and seven assists for 19 points in 40 games, with a grisly -24. The three-year player card still looks stellar. Here’s Evolving Hockey’s:

And here’s the JFresh card:

The question that Kyle Dubas and his scouts no doubt discussed: What version of O’Reilly are we getting? The one through last season was an unequivocally excellent all-around player, but this year has been tough. Some of the player cards, like the JFresh one, do not indicate much slippage, whereas Evolving Hockey’s — and obviously, the counting stats — do.

There are a few contextual factors to think about here. First of all, the Blues are a much worse team this season compared to any year since O’Reilly joined the team. He had issues gelling with linemates early on, including Jordan Kyrou, and some of Kyrou’s struggles may have affected O’Reilly. And then there was the injury; O’Reilly missed over a month with a foot injury that he just recently returned from.

What likely had some sway on Kyle Dubas is O’Reilly’s play in the limited sample since he returned to action. In his last three games, he has posted two goals and three points with a plus-five rating, putting seven shots on goal and winning 63% of his faceoffs. O’Reilly has owned 66.35% of the expected goals, 58.7% of the scoring chances, and 56% of the high-danger chances at 5v5 in those three games, per Natural Stat Trick.

He has legitimately looked like the old O’Reilly, and while it might have been ideal to wait for a few more games to confirm O’Reilly is back to his old self, the early returns were positive enough for Dubas to strike.

A healthy, 2022 version of O’Reilly is a dynamite add for this team, and Dubas must believe that he’s seen enough from RO’R over the past week to believe the 2022 O’Reilly is back.

O’Reilly’s fit

Photo: USA Today Sports

There are a great number of reasons why last year’s (or 2021 or 2020 or 2019, etc) Ryan O’Reilly is a tremendous fit for the Leafs, but let’s start with the positional need.

The team was previously one Tavares or Matthews injury away from Alex Kerfoot or Pontus Holmberg lining up as their second-line center. They arguably now have the best center depth in the NHL.

If Sheldon Keefe wants to, he could roll with Matthews 1C, Tavares 2C, O’Reilly 3C, and David Kämpf 4C. O’Reilly gives the Leafs a play-driving center who could potentially anchor a third line that has some scoring juice.

On the flip side, O’Reilly also is plenty good enough to play in the top six, and if needed, he could jump up to the second-line left-wing spot, too. Perhaps it’s most likely that Keefe uses O’Reilly at 3C to start most of the games, but he bumps him up if the Leafs need offense late in a game or when closing out a game. O’Reilly is the definition of a versatile hockey player who can be used basically anywhere in the lineup and in any situation.

Which is a big part of the appeal of O’Reilly. His defensive results have slumped some this season according to some models (again, how much of that is team/linemate effects?), but at his best, O’Reilly is a dominant 200-foot player (and was as recently as last year) who controls his shifts at the level of some of the best centers in the NHL.

His PK results have never been as great as you might think, but his 5v5 defense has always been as good as it gets. He’s a menace in the defensive end — a master of the stick lift and poke check, jarring pucks free and creating turnovers. O’Reilly has consistently been one of the NHL’s best faceoff men and is huge for those crucial DZ draws, firing at a 56.9% faceoff clip over the past three seasons. He has experience playing against elite competition defensively and winning those minutes with regularity as a center while driving his line.

On the offensive end, his production this year is a bit disappointing, but he’s typically been a shoe-in for between 60 and 80 points and a safe bet for 20-25 goals. He has a good shot, although he is not a high-volume shooter; more of a pass-first player who shoots when he has a solid chance to score and converts on ~11.5% of those across his career.

O’Reilly is a pass-first player — he has excellent vision — and the measly seven assists this season seem to be the consequence of his linemates’ poor finishing than evidence of a decline in his passing, as this graph shows:

This also helps explain his -24 plus/minus stat. His goalies aren’t making saves when he’s on the ice, and his wingers can’t put the biscuit in the basket.

O’Reilly has never been a great burner, but at 6’1″, 207 lbs., his body is built for playoff hockey and he has been an elite puck retriever and generator of cycle chances over the duration of his career.

O’Reilly’s not going to be dangerous off the rush the way Timo Meier would, but he will grind on opponents on the forecheck. O’Reilly’s PP results haven’t been great this year, but he is typically a highly-effective player from the bumper slot on the PP, which is another option that the Leafs could use offensively.

The combination of a good shot when he uses it, superb vision, and strength in puck battles is the O’Reilly offensive package, and when we add it to the 5v5 defense and faceoff acumen, he is as complete of a player as it gets. So long as he’s healthy.

Of course, I would be remiss talking about RO’R without discussing the intangibles. He’s a former Conn Smythe winner and instantly gives the Leafs more of a playoff pedigree. There aren’t too many Leafs on this roster who have won the Cup, especially with Muzzin out (and considering that Murray seems to be the backup right now), and O’Reilly gives them one.

He’s not just someone who picked up a ring somewhere along the way, either. Removing the playoffs at age 18 when he was a rookie for Colorado, O’Reilly has a 21-34-55 line in 58 playoff games since then, including 7-5-12 in 12 games last year. O’Reilly is a gamer who simply shows up, scores, and wins in the playoffs.

O’Reilly has also won the World Championships twice with Canada in 2015 and 2016 as well as the World Cup of Hockey in 2016 and the Hlinka-Gretzky Cup back in 2008. This is a player who wins, and who often does it in a leadership role (he has served as St. Louis’ captain since Alex Pietrangelo departed). From an intangibles and playoff pedigree standpoint, O’Reilly rates as a 10/10.

Noel Acciari’s fit

Photo: USA Today Sports

The depth add in this deal, Acciari is enjoying an excellent season for St. Louis after fading from the limelight in Florida.

The 31-year-old emerged with the Boston Bruins organization and was in their everyday lineup for both the 2018 and 2019 teams that broke the hearts of Leafs Nation. He was a fourth liner then and didn’t produce much given his limited role, and after losing the 2019 Stanley Cup Final (ironically, to O’Reilly’s Blues), Acciari signed a contract with the Florida Panthers.

In the sunshine state, Acciari rode a 18.5% shooting percentage season to 20 goals in 66 games for Florida and then got the other end of that sword in 2020-21, scoring just four in 41 games due to a 5.9% shooting percentage.

Last year, he was bumped out of Florida’s uber-deep forward lineup and played just 20 games, but in the offseason, he landed with St. Louis, where he has cobbled together a major redemption season. He’s scored 10 goals and 18 points in 54 games, shooting 13.3% with respectable underlying numbers.

Acciari is a player I liked from the eye test in Florida, even if the analytics weren’t always there. He’s an effective forechecker and penalty killer, someone who can do a little bit at both ends of the ice and retrieve the puck. He’s good defensively and is producing a fine season on the PK:

The shooting makes up his value in a WAR-based model like the JFresh one, and this year it is good after a couple of seasons that were below average. Make of that what you will, but Acciari can impact the game whether he’s scoring or not, which is why Boston kept him in the playoff lineup for their Cup Final run despite him scoring just two goals in 19 games.

On that note, Acciari also brings playoff experience, even if he doesn’t possess a Cup ring. He has played 54 career playoff games — 15 more than Mitch Marner has played in his career, for example. That’s not nothing, and if Acciari is bumping, say, Joey Anderson out of the lineup, it’s a clear upgrade for the Leafs.

He is a respectable bottom-six player who can play wing or center and help the PK, which is an area of emphasis considering the path through Tampa and likely Boston in the playoffs.

Projecting the lineup & first thoughts on the deal

Photo: USA Today Sports

Here’s a quick possible lineup projection for the Leafs with both of these players in the fold:


Zach Aston-Reese is also around as a spare (you can swap him in instead of Holmberg, should you so choose).

As I stated earlier, the Leafs could bump O’Reilly up to the second line if they want, they can move Acciari to center if needed, and so on. These additions give Sheldon Keefe loads of options.

Finally, we must talk about the price. The Leafs paid a significant cost and did it for two pending UFAs. They gave up their 2023 first (although if the draft were today, it would be pick #26 and could be later if the team were to go deep in the playoffs), their 2024 second, Ottawa’s 2023 third from the Matt Murray trade, and a 2025 fourth.

That leaves the Leafs with just a third, fifth, and sixth for this June’s draft, and it also leaves them without a second in either 2024 or 2025. They are light on draft capital moving forward, but in moving only Mikhail Abramov out of their prospect pool, they kept the farm system intact.

Abramov was a falling prospect in the grand scheme of things, and Toronto did not have to surrender Matthew Knies, Topi Niemela, Nick Robertson, or Fraser Minten, who represent quicker help than any of these draft picks (which may not be on the team until 2025 or later).

A crucial element to note is that St. Louis retained 50% of O’Reilly and Minnesota retained 25%, which drove the cost up but also helps the flexibility of the Leafs. O’Reilly’s cap hit is just $1.875 million as a result, leaving the team with cap room to keep more players on the roster than the bare minimum in the regular season.

It also gives Dubas the ability to add a defenseman, too, if he wanted. I’m not sure if he will, but it does leave the door open for the final two weeks before the deadline. Moreover, getting Minnesota involved for retention means that the Leafs can hang onto all of their current roster players.

Given the price especially, one question for Leafs fans will naturally surround the possibility of a contract extension. Would O’Reilly be open to sticking around? It was reported that he loves St. Louis and was considering staying with the Blues (or returning in the offseason if he was traded), but he is an Ontario boy and may be interested in playing for his home-province team.

If O’Reilly wants to cash in — which he’s completely earned the right to do — then it likely won’t be a fit. But let’s say he wants to play for a contender and is willing to re-sign for $3 million? I think the Leafs could make that work (you may have to move on from Kämpf, but would anyone be crying about choosing RO’R over Kämpf?). At 32, you have to be careful about term, but if O’Reilly is willing to keep the term shorter, consider me intrigued by the idea.

At the end of the day, O’Reilly made oodles of sense as a fit for the team, with the ability to play center and contribute in just about every aspect of the game. The intangibles are something this team needs as it looks to get itself over the playoff hump. He also helps the team defense aspect and adds the additional secondary scoring Toronto needed.

Acciari augments the bottom six and PK and makes the forward group much deeper. On the recent MLHS podcast, we talked about wanting Zach Aston-Reese to be the 12th-best forward, not the 10th-best; adding O’Reilly and Acciari makes him the 12th-best on this Leafs’ roster. Mission accomplished.

The price is sizable, but those draft picks aren’t helping for years and years into the future. O’Reilly and Acciari help move the needle now, without giving up any prospects of note.

If Matthew Knies is indeed a stud (who knows if he is), he will be able to help the Leafs in 2024 and 2025. The 2023 pick they gave up won’t be helping them in those years, so it was the correct asset to give up. There is not an insignificant risk involved here, but it’s a huge vote of confidence in the players. Their odds against a team with the depth of a Boston or Tampa just improved notably, and there is no doubt the core four are over the moon about this.

With his elite players under contract and currently in their primes, it was incumbent upon Kyle Dubas to take this swing. Few other trade candidates checked as many boxes as bringing home a former Conn Smythe-winning, high-end two-way center.