What could a Damian Lillard trade look like in the NHL?

The Portland Trail Blazers blockbuster trade of their franchise icon has us thinking: what could an NHL version look like?

Damian Lillard successfully manipulated a trade to the Milwaukee Bucks on Sept. 27, a seismic deal that altered the landscape of the NBA and the immediate fortunes of about a half-dozen teams. It’s the type of move that NHL fans and consumers are inherently jealous of.

Lillard, a seven-time All-Star who operates as one of the most lethal scorers of his generation, demanded a change of scenery — with a stated goal of joining the Miami Heat — after spending the first 11 seasons of his career with the Portland Trail Blazers. Portland received 2018 first overall pick Deandre Ayton, a 2029 first-round pick, pick swaps in 2028 and 2030, and Jrue Holiday, arguably the league’s best defensive player. Holiday was then flipped to the Boston Celtics in a subsequently intriguing deal for Malcolm Brogdon, Robert Williams III and two future first-round picks.

It's Dame time in Milwaukee after a blockbuster trade, but what would an NHL version of that deal look like? (Photo by Patrick McDermott/Getty Images)
It's Dame time in Milwaukee after a blockbuster trade, but what would an NHL version of that deal look like? (Photo by Patrick McDermott/Getty Images)

Not only are blockbuster trades the lifeblood of the offseason and a terrific excuse to take the afternoon off to discuss sports, it’s an avenue to materially impact several teams at a time. Last summer’s Matthew Tkachuk-Jonathan Huberdeau trade dramatically affected the fortunes of the Panthers and Flames, the former riding Tkachuk’s clutch scoring to the Final while Huberdeau regressed by 60 points and could be dangled in another trade as the Flames aim to find some direction.

And frankly, fans are starving for another deal of this magnitude.

What would an NHL version of the Damian Lillard trade look like?

There are a few caveats: NBA superstars inherently have more value than their NHL counterparts as it is much easier to directly influence a game when you’re playing 40 minutes a night and have usage rates that would be untenable in hockey. Lillard was named to the NBA’s 75th anniversary team — a distinction that perhaps overlooks his glaring defensive woes — wanted out of Portland and his move to Milwaukee forms the NBA’s most dangerous 1-2 punch alongside Giannis Antetokounmpo.

Hellebuyck to the Lightning, Stamkos to the Devils, Jets aggressively start tanking

Lightning receive: Connor Hellebuyck

Devils receive: Steven Stamkos

Jets receive: Alexander Holtz, Seamus Casey, Tanner Jeannot, New Jersey’s 2024 and 2026 first-round picks, Tampa Bay’s 2024 third-round pick

Why it works/why it doesn’t work: Woooooooo, baby, now this is a trade! Stamkos will play the role of Damian Lillard here, with his matching seven All-Star selections and game-breaking scoring ability.

Tampa Bay’s captain set off a firestorm when he revealed his frustrations over stalled contract negotiations and he’s slated to become an unrestricted free agent. Andrei Vasilevskiy is out for at least two months and the Lightning badly need a starting goaltender. Getting one of the league’s five best goaltenders is not only a contingency plan, it’s a luxury.

Steven Stamkos is the perfect candidate to play the role of Lillard amidst his squabbles with Lightning management. (Photo by Mark LoMoglio/NHLI via Getty Images)
Steven Stamkos is the perfect candidate to play the role of Lillard amidst his squabbles with Lightning management. (Photo by Mark LoMoglio/NHLI via Getty Images)

Stamkos would join a Devils team primed for contention and could be reunited with former linemate Ondrej Palat. He would give one of the league’s leading contenders instant credibility and pedigree, and it’s frightening to think what the upstart Devils could do with yet another perpetual 35-goal threat on their hands. Last week, we suggested that the Devils leverage their deep prospect pool for top-tier talent and this deal would be a prime example.

Hellebuyck has been one of the league’s best goaltenders for several years but this iteration of the Jets isn't good enough to win a Cup and it may be in their best interest to start offloading their assets while trying to accelerate a rebuild. The 30-year-old is slated to become an unrestricted free agent and would be a rental piece for a Lightning team that doesn’t have time to care about tomorrow while trying to squeeze another Cup in.

For their troubles, Winnipeg will receive a former first-round pick in Holtz, two more first-rounders from the Devils and a third-round pick from the Lightning to get Stamkos off their hands and Tanner Jeannot to help alleviate some of Tampa Bay’s salary cap woes. It’s not perfect and it assumes Winnipeg will (it should!) begin its rebuild expeditiously.

Hellebuyck for Stamkos straight up

Lightning receive: Connor Hellebuyck, Nino Niederreiter

Jets receive: Steven Stamkos, Tanner Jeannot

Why it works/why it doesn’t work: This trade would help the Lightning and Jets get ahead of the curve as Stamkos and Hellebuyck are slated to test free agency. Jeannot and Niederreiter are included to balance each other’s cap sheet out and the latter is under contract through 2025.

Stamkos may be pissed off now, but it would be scorched earth to trade him to a Winnipeg team lacking direction against his will. He also has a no-movement clause, so it may be back to the drawing board.

Stamkos heads West, Elias Lindholm to Lightning

Flames receive: Steven Stamkos

Lightning receive: Elias Lindholm, Yegor Sharangovich, Calgary’s 2024 first-round pick, Calgary’s 2025 second-round pick

Why it works/why it doesn’t work: Provided that Stamkos sees the vision in Calgary and is amenable to joining a Flames forward corps that looks great on paper, this could potentially work. If Stamkos can reinvigorate a Flames team that recorded 111 points two years ago, it could be a rare win-win trade.

Lindholm is one of the league’s premier defensive forwards and is also an unrestricted free agent at the end of the year. It’s been reported that the Flames may sign Lindholm to an extension prior to the season but if Tampa Bay were on the table, one could imagine the 28-year-old having second thoughts. Sharangovich is an underrated piece as well who is two years removed from a 24-goal season, keeping Lightning competitive and flexible.

Of course, this is predicated on Stamkos and Lindholm being upset with their respective teams and it’s quite possible that both players remain with their current teams for the duration of their career. But again, this is just a thought exercise for now and we’d like to see another blockbuster trade, for the drama and the exciting prospect of revamping the NHL’s competitive balance.