NHL Best Bets Today | Expert Picks for Monday, December 23

Two Original Six matchups headline Monday’s NHL slate, and both are dripping with desperation. The Penguins and Maple Leafs meet in Toronto with both teams clinging to playoff relevance after brutal stretches, while the Canadiens and Bruins renew their rivalry in Boston with the holiday break looming and neither team able to afford another loss.

Toronto’s lost five of six and just got boat-raced on a three-game road trip. Pittsburgh snapped an eight-game skid but still needs to prove it can string wins together. Meanwhile, Boston’s given up 18 goals in four games at home, and Montreal’s rolling into TD Garden with momentum and a hot second line. These aren’t pretty games — they’re survival games. And that’s exactly where I think the value lives.

Let’s get into it.

1) Penguins ML (+121) | Pittsburgh at Toronto

Edge in one line: Pittsburgh controls play at 5-on-5, runs a solid power play, and you’re getting plus-money on a team that should be priced closer to a coin flip.

Breakdown

Toronto is 1-for-14 on the power play and has allowed 14 goals in its last three road games. That’s not bad luck — that’s a full-on special teams collapse.

The Leafs are home and desperate, sure. But desperation doesn’t fix a power play that’s colder than a February night in Saskatchewan, and it doesn’t suddenly make their defensive structure airtight against a Pittsburgh team that thrives in transition. The Penguins have the better special teams, the better blue line, and more offensive zone time. At +121, you’re getting paid to back the team controlling play lately — and now riding a spark after watching Captain Sidney Crosby become the franchise’s all-time leading scorer.

Player Props

#1: Sidney Crosby Over 2.5 Shots on Goal

Crosby just became the franchise’s all-time points leader, and he’s still the engine of Pittsburgh’s offense. Toronto’s defensive structure has been swiss cheese off the rush, and Crosby feasts in high-slot areas where the Leafs have been bleeding chances. He’s averaging 2.4 SOG per game this season (84 in 35 games), but that number climbs when he’s getting PP chances and facing a team that allows volume like Toronto does. 

#2: William Nylander Over 0.5 Points

Nylander’s snake-bitten on goals (zero in 11 games), but the process is still humming. He’s racked up 17 shots and 5 assists during the drought, which tells you he’s creating chances and still contributing in other areas. The Pens have allowed six power-play goals in five games — and that’s exactly where Big Willy Styles does his damage when he’s due. I’m ok with a sprinkle on anytime goal in this spot as well.

2) Over 6 Goals (-107) | Montreal at Boston

Edge in one line: Boston’s defense has been a turnstile for high-danger chances, Montreal’s second line is rolling, and the last game before Christmas break typically means aggressive hockey with teams emptying the tank before a nice break.

Breakdown

The Bruins have allowed 18 goals in their last four games, including two six-goal beatdowns at home. Lately, their defensive structure looks less like a system and more like pond hockey.

They’re giving up quality looks from the slot, and Jeremy Swayman’s been left on an island more often than Tom Hanks in Cast Away. Meanwhile, Montreal’s been quietly dangerous, going 4-1-2 in their last seven with their Demidov-Slafkovsky-Kapanen line creating chances in bunches.

Four of Boston’s last five games have sailed over the total, and four of the last five meetings between these two in TD Garden have hit 6+ goals. Add in the pre-break energy where teams tend to play loose and take more risks, and you’ve got a recipe for a 4-3 or 5-2 type game. Even if it’s 3-3 in regulation, you’re getting overtime to push you over. At -107, this line should be closer to 6.5.

Player Props

#1: Cole Caufield Over Shots on Goal

Caufield’s the Canadiens’ primary offensive weapon, and when they’re trailing or pushing for a goal, he’s the trigger man. He’s hit 4+ shots in four of his last six games against Boston, and the Bruins’ defensive structure leaves openings on the left side — exactly where Caufield operates.

#2: David Pastrnak Anytime Goal

Pastrnak’s been quiet lately, and that usually means he’s about to explode. The Canadiens’ penalty kill has been shaky at best, and if Boston gets a power play or two, Pastrnak will have prime opportunities from his office on the left circle. He’s due, the matchup is soft, and the situation screams breakout performance for him.