Winter Classic 2023: What to Watch as Bruins, Penguins Take Fenway Park

The Boston Bruins and Pittsburgh Penguins are two storied NHL franchises that have given fans so much over the past two decades.

Both boast legendary cores that have stuck together through it all: Sidney Crosby, Kris Letang and Evgeni Malkin have played in Pittsburgh for 17-plus years. Meanwhile Patrice Bergeron, Brad Marchand, David Krejci and rising star David Pastrnak are continuing the Boston legacy that also features recent retirees Tuukka Rask and Zdeno Chara.

Both cores have set examples for the entire league regarding loyalty and leadership, and they've seen it pay off with perennial trips to the playoffs resulting in three Stanley Cups for these Penguins and one for these Bruins.

The 2023 Winter Classic at Fenway Park on Monday is a rare opportunity to give the players who have shaped a generation of hockey their flowers while they're still in the league.

Let's prepare to do so with the biggest storylines leading up to the game.

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The Bruins Are Almost Comically Good

Aside from the team and the fans, perhaps no one is enjoying the Bruins' historic regular season more than the geniuses who gave them the 2023 Winter Classic.

Many had their doubts about the Bruins heading into the season. They suffered a first-round exit in 2021-22, the futures of captain Bergeron and staple Krejci were up in the air, and there were plenty of injuries to key players such as Marchand (hip), Charlie McAvoy (shoulder) and Matt Grzelcyk (shoulder) to worry about.

But Bergeron and Krejci re-signed and are playing as well as ever, Linus Ullmark is on a Vezina Trophy-caliber run, Pastrnak more than kept things going while his injured teammates were recovering and the Bruins are the best team in the league at 28-4-3.

They're beating good teams. They're crushing bad teams. It feels like they're doing it all with ease.

Every time you wonder if they're going to slow down, they beat the Jets once and the Devils twice for good measure.

Boston is on pace to finish the regular season 66-9-7, which would be the best record in the modern NHL by far, besting the 62-13-7 Detroit Red Wings from 1995-96.

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It's Gut-Check Time for the Penguins

The 2022-23 Bruins are breaking records and are on pace to break many more, but let's not disrespect their opponent—the Penguins have assembled a decent season despite a bad start and a rocky present.

Pittsburgh has a 19-10-6 record to show for all its ups and downs, with stretches of greatness and stretches of not-so-greatness along the way. While I'm not a fan of the loser point and could use this record juxtaposed against the Penguins' No. 3 spot in the Metropolitan Division to further slander the loser point, Pittsburgh has played better than its record—until recently.

And we do have to address their pattern of concerning collapses. The latest—a blown 4-0 lead resulting in a 5-4 Red Wings win Wednesday—came with more bad news. Letang, the team's star defenseman who had just returned after fully recovering from a stroke, is being evaluated for a lower-body injury and may not play.

The already depleted blue line has a lot of work to do if Pittsburgh is to win the Winter Classic, but a victory at Fenway Park against the best team in the league has all the makings of a season turning point. This could be the wake-up call the Penguins need to consistently play at the level they've shown us they can in spurts this season.

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Sidney Crosby Is Still Sidney Crosby

Crosby has spoiled us so much over the years that sometimes we take his continued excellence for granted.

All the highlight reels feature flashy plays from Connor McDavid, Leon Draisaitl and Tage Thompson, and that's fine. But at 35 years old, Crosby quietly ranks No. 9 in the league with 43 points (19 goals) in 35 games.

He's still got it, and he's an important constant in Pittsburgh's season of ups and downs. If anyone can get this team back on track for at least one more playoff run, it's No. 87. And if there's any place to do it, why not Fenway Park?

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Ullmark Is Playing Vezina-Caliber hockey

Ullmark always had potential to be a great goalie, but the Sabres were so bad when he was in Buffalo's net that even he couldn't save them.

Now the stars are aligning for everyone's favorite esports lover, and he's making a serious case for the Vezina. He's leading the league in every relevant goaltending metric with his 1.90 goals-against average, .938 save percentage, 20-1-1 overall record and 20.4 goals saved above expected, per Money Puck.

The Winter Classic is just one game, and with all of the elements, glare and fanfare surrounding the event, it's not a big deal if Ullmark doesn't have the best outing of his life. But a few highlight-reel saves at Fenway would be a welcome addition to the Vezina highlight video at the end of the year. Just sayin'.

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I Just Hope Everyone Has Fun

As mentioned, the Winter Classic is a rare opportunity to give some of the previous decade-defining players their flowers while they're still playing.

We've been enjoying milestone events such as Bergeron's 1,000th point and Malkin's 1,000th game this season, and as esteemed as those accomplishments are, they're making me feel old and a little bit sad. Like most millennial hockey fans, I grew up with these players.

Bergeron didn't just teach me how to play hockey, he taught me how to play it the right way, and he showed everyone there's longevity and greatness to be found in the fundamentals.

Malkin didn't just teach me how to score, he taught me I could be score. Marchand taught me that I'm allowed to be a little annoying if I'm really good at what I do. And of course, Crosby taught me that the love of the game means everything.

I don't know about you, but I'm so excited to watch these legends in one more outdoor game. Maybe it's a perfect new-year opportunity to stop looking back to what was and start looking forward to what might be.

Just this once, let's pause and enjoy the greatness.