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Winnipeg Jets Valuation - Jan. 2 2026 - Vol. 79 Issue 6 - Jared Clinton

NHL VALUATIONS

$1.35B FORBES

$1.33B SPORTICO

$1.5B ROUSTAN

OWNERSHIP - MARK CHIPMAN

IT’S HARD TO believe it has already been 15 years since the Jets returned to Winnipeg. And as time passes, it’s equally hard to believe that Mark Chipman was able to make his dream – and the dream of many of his fellow Winnipeggers – a reality.

Consider that when the original Jets franchise left Winnipeg in 1996, it came at a time when relocations were coming in fairly quick succession. The Minnesota North Stars, Quebec Nordiques and Hartford Whalers had, in the several years prior, moved to Dallas, Colorado and North Carolina. Look back a couple of decades further, too, and the NHL had moved on from Atlanta, Kansas City and Cleveland. And more often than not, it’s been the case that the league has not returned to the markets from which it has departed. For a time, Minnesota and Atlanta were the lone exceptions.

But while other former NHL cities bided their time waiting for the big league’s return, Chipman’s gambit was a clever one. In the wake of the Jets flying south to Arizona, he snapped up the then-IHL’s Minnesota Moose, moved the club to the old Winnipeg Arena and, over the next decade-plus, offered what those in the C-suite refer to as proof of concept: Chipman’s True North Sports & Entertainment showed – through fan support and building a new downtown arena, among other things – that Winnipeg was ready for the NHL’s return.

At no point since the Jets’ return has True North rested on its laurels, however. On ice, the ownership group has backed the product financially, including ponying up big money in recent contracts for stars Mark Scheifele, Connor Hellebuyck and Kyle Connor. This, too, comes after the team captured the Presidents’ Trophy. Meanwhile, away from the rink, True North has put shovels in the ground and reshaped much of Winnipeg’s downtown core.

With the arena as the centerpiece, the real-estate arm of the business set to work creating True North Square. The four-tower site offers residential, office and retail spaces, with room set aside for an incoming hotel property. Last December, True North expanded its reach and influence in downtown with the acquisition of the former Portage Place mall. Plans are in place to develop the space – a sprawling 1.2 million square feet – with parks, retail and community spaces. The anchor tenant will be a 265,000-square-foot healthcare facility, while a partnership with Southern Chiefs’ Organization will also see True North develop a 15-storey residential tower, which will designate as many as 40 percent of its units as affordable housing.

FEATURED BUSINESS EXECUTIVE - JOHN OLFERT

PRESIDENT AND CHIEF OPERATING OFFICER

IT WAS ONLY A decade into his professional life, 10 years after his graduation from the University of Winnipeg in 1991, that John Olfert began his tenure with True North. In his earliest days with the company, he served in various roles, eventually rising to chief financial officer in 2002, in the midst of True North working toward the construction and eventual opening of the now-Canada Life Centre in 2004.

In the 20-plus years since, Olfert has been integral to the business operations and expansion of True North Sports & Entertainment’s on- and off-ice ventures. To wit, he helped execute the purchase of the Jets, brought the AHL’s Manitoba Moose back to Winnipeg and was at the center of True North’s acquisition of the iconic Burton Cummings Theatre.

GOVERNOR & ALTERNATE GOVERNORS - MARK CHIPMAN

ALTERNATE GOVERNORS: Kevin Cheveldayoff, John Olfert, Patrick Phillips

FEATURED HOCKEY EXECUTIVE

KEVIN CHEVELDAYOFF - GENERAL MANAGER AND EXECUTIVE VICE PRESIDENT

KEVIN CHEVELDAYOFF DOESN’T ALWAYS get the credit he deserves. Whether it’s player polls or comments from the athletes themselves, Winnipeg tends to top the list of least-desirable destinations. That puts Cheveldayoff at a disadvantage in free agency and has played a part in key contributors asking out. Yet, in almost every instance, Cheveldayoff and the Jets have come out on the winning side of those deals, whether it was the Jacob Trouba swap, the Patrik Laine deal or even the subsequent Pierre-Luc Dubois trade.

Perhaps the ace up Cheveldayoff’s sleeve, though, is that Winnipeg has proven to have something of a Hotel California-esque trait of late: once talent checks in, they don’t want to leave. Scheifele, Hellebuyck and Connor are examples, but the Jets have also had little trouble negotiating long-term extensions for Gabe Vilardi, Neal Pionk and Adam Lowry. In no small part, that comes down to culture on and off the ice – and Cheveldayoff is key in the development of that culture.

SOCIAL MEDIA STRATEGY

THE JETS, DON’T view social media as a necessity but an opportunity – a chance to communicate with the community, engage with fans and take viewers, in the arena or at home, into the game in new ways. And that approach hasn’t gone unnoticed. At the NHL’s club business meetings last July, the Jets were presented with the Stanley Award as social media club of the year.

What has helped set the Jets’ social offerings apart is their dedication to creating social-first content. The strategy has been led, in part, by Adam Krueger, who joined True North in 2022 after several years with Maple Leaf Sports & Entertainment. He leads the Jets’ social team as director of social and content. Meanwhile, Tyler Esquivel is one of the familiar faces to fans. As the Jets’ content manager, Esquivel often appears on camera interviewing fans and players alike.

One area of particular success for the Jets has been YouTube, where the team has grown its channel and found new ways to take fans behind the scenes. Among the offerings is a live pre-game show, hosted by former national broadcasters Sara Orlesky and Jamie Thomas, and live post-game interview footage that provides instant access to thoughts from players and the coaching staff. The game-day coverage is in addition to off-ice video content, including personality pieces such as Home Ice and the Ground Control podcast.

Perhaps the most significant piece of the Jets’ YouTube puzzle, though, is Runway, a behind-the-scenes documentary series that follows the team throughout the season. Following in the footsteps of several other clubs, such as the Boston Bruins and Pittsburgh Penguins, the series launched in 2022-23 and has gained increased traction not only online but through its use as intermission content during TSN broadcasts.

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As the Milan-Cortina 2026 Olympic break begins, the San Jose Sharks are enjoying a season that even their most optimistic fans might not have anticipated. Sitting just five points outside the Western Conference Wild Card playoff spots after 55 games, the Sharks are quietly positioning themselves for a potential return to the Stanley Cup postseason.

While the front office will turn its attention to cheering on Macklin Celebrini and the other Sharks representing their countries, the looming NHL Trade Deadline is also on the horizon. The question now is how GM Mike Grier will navigate it. Will he lean toward adding veteran depth to give the team a playoff boost, or will he hold back, conserving assets for the future?

Just an amazing display of sportsmanship by Macklin Celebrini! 👏 pic.twitter.com/6Oiw8TqU5b

— NHL (@NHL) January 31, 2026

Sharks Will Buy at the Deadline, But...

This season has already been a massive success for the Sharks. Now that's not to say that they can't improve any further before the playoffs begin, but when you think back to the last handful of seasons and how the Sharks were literally in last place in just about all of those years, to come back this year and be considered a fringe playoff contender is a huge improvement.

The Sharks of today remind me a bit of the Colorado Avalanche in the early 2010s. That Avalanche team built its core through the draft, selecting players like Gabe Landeskog, Nathan MacKinnon, Mikko Rantanen, and others. But beyond their young stars, they also focused on strengthening their defensive corps, acquiring Erik Johnson from the St. Louis Blues and drafting Bowen Byram, while adding key pieces like Nazem Kadri and Andre Burakovsky. Over the years, they steadily worked to improve their goaltending and overall depth.

It was a long, deliberate process—it didn’t happen overnight. After the 48-point season in 2016–17, the organization faced tough decisions and difficult conversations, and not everyone was willing to stick around. The bottom line, though, is that they persevered and stayed the course together.

The Sharks might reach that level faster than the Avalanche did. They have a generational talent in Celebrini, a dynamic playmaker in Will Smith, and recently added Kiefer Sherwood to bolster the roster. With the team’s recent success, some have argued that GM Mike Grier should be serious buyers at the trade deadline in hopes of making a deep playoff run. However, there’s a significant risk-reward calculus involved in pursuing that approach.

Perhaps it was just the word usage, but when I hear serious buyers, I'm thinking the go for broke mentality, which I don't think is necessarily a good strategy. We're very early into the Sharks rebuild. You have a very solid foundation. Now you just need to add pieces that can steadily build this team into a Stanley Cup contender. I think the Sharks are already playoff contenders. Yes, they've lost their last four games; the Olympic break is upon us, and now the team can sit down and evaluate to see where they need the most help.

Defense

The Sharks have allowed 193 goals this season, the sixth-most in the Western Conference—and you can’t place all the blame on the goaltenders. Yaroslav Askarov has been brilliant at times, but he’s also had his share of forgettable moments. More often, though, the problem lies elsewhere: when a team consistently turns over the puck in its own zone, it inevitably leads to scoring chances against. At some point, goals are going to happen—that’s the law of averages in a nutshell.

The next step for the Sharks to improve their chances of becoming true playoff contenders isn't offense, it's adding a shutdown defenseman. For instance, Ryan Shea, a Pittsburgh Penguin, is set to become an unrestricted free agent at the end of the season. He has emerged as a dependable, steady, and physical force on the Penguins’ blue line, frequently paired with Kris Letang in a shutdown role tasked with containing opposing top-six forwards.

Letang, who's won three Stanley Cups as a Penguin, is one of the best offensive defensemen of his era, is currently week-to-week with a fractured foot and has a significant injury history, but his accomplishments are written in stone. And Shea is having a career-best season right now. Through 56 games, he's posted three goals and 19 assists for 22 points with a plus/minus rating of +21. The Penguins are a rebuilding team. It wouldn't hurt to try to float a trade idea and offer a 2026 second round pick to sweeten the deal, but these are just ideas.

The bottom line is that the Sharks aren't going to make a deep playoff run one way or another this year, but the foundation to becoming a Stanley Cup champion down the line is here. It's just about adding the right pieces and getting the juicy flavors and the chemistry flowing. The Sharks are easily the most improved team in the NHL. What happens next is up to them. The puck is in their court.  

The Montreal Canadiens will be a team to watch once the NHL Olympic trade freeze passes. With the Canadiens currently being second in the Atlantic Division standings, it would not be surprising in the slightest if they look to add to their roster ahead of the trade deadline. 

Now, the Canadiens are being connected to one of the NHL's top trade candidates. 

During his most recent 32 Thoughts column for Sportsnet, NHL insider Elliotte Friedman wrote that he believes the Canadiens "like" Nashville Predators star center Ryan O'Reilly. 

"Eric Engels dropped a really good interview with Jeff Gorton. My theory is they like Ryan O’Reilly," Friedman wrote. 

The Canadiens being viewed as a possible suitor for O'Reilly is not surprising in the slightest. The 34-year-old would be a great addition to the Canadiens' top six if they acquired him, as he is a very good two-way center who produces well offensively, kills penalties, and is a well-respected leader. With this, he would be a big-time pickup for a Canadiens club on the rise. 

O'Reilly would also be more than a rental for the Canadiens if acquired, as he has a bargain $4.5 million cap hit until the end of the 2026-27 season. Thus, he would help the Canadiens beyond this season, which adds to his appeal. 

In 57 games this season with the Predators, O'Reilly has recorded 20 goals, 36 assists, 56 points, and a plus-8 rating.