The dog days of the NHL off-season can feel like they arrive faster than a sprinting greyhound. The action surrounding the late-June draft and start of free agency on July 1 is intoxicating, but as days and weeks go by, NHL ennui sets in during the summer’s hottest days.
It just seems like nobody wants to move.
That said, it’s become increasingly common for significant trades to occur between mid-July and the start of training camps in September. And if Sportsnet’s Eric Engels can be believed, this summer could take that to another level.
“It’s quiet now, we’re in the dead of the off-season, people are taking a break — it’s a long year, they work around the clock — but they are not far from their phones,” Engels said earlier this week on The Sick Podcast with Tony Marinaro. “Somebody gets an idea, and all of a sudden a name shakes loose and it could crack open a whole other secondary market. I don’t think that’s going to happen imminently or immediately, but I think people are a little closer to their phones this summer (than previous off-seasons). It’s just the nature of how competitive the league is right now and the fact money has come into the system (in the form of a rising salary cap).”
Who could those players be? Well, on Tuesday, Sportsnet’s Nick Kypreos dropped his latest off-season trade board and it represents a wide spectrum of players, from in-his-prime sniper Jason Robertson to veteran centre Nazem Kadri to offence-first defenceman Erik Karlsson, who’s actually been a key figure in a couple off off-season trades before.
Mention midsummer trades from the past few years and you’ll surely have somebody reference the July 22, 2022, mega-trade that sent Matthew Tkachuk from Calgary to Florida in exchange for MacKenzie Weegar and Jonathan Huberdeau. That trade, however, actually occurred only nine days after the start of free agency, which was pushed to July 13, 2022, because of the NHL still be slightly off its axis thanks to the COVID-19 pandemic.
Still, there are plenty of examples of significant moves that occurred between this part of the calendar — at least two weeks past the start of free agency — and the beginning of training camps in September. With that in mind — and with the hope there could be some sizable swaps still to come this off-season — we thought we’d offer up a summer patio-esque appetizer and run down some of the most notable off-season deals from the past 10 years. (We excluded the 2020 and ’21 off-seasons because they were so outside the realm of a normal NHL break.)
Erik Karlsson to the San Jose Sharks, Sept. 13, 2018
Karlsson was entering the final year of his contract ahead of 2018-19 and it became pretty evident during the summer of 2018 that his time in Ottawa was up. The Sens — after nearly making the 2017 Stanley Cup Final — were coming off a miserable 2017-18 campaign, which wound up being the first of seven consecutive non-playoff seasons.
San Jose — still in go-for-it mode after making the 2016 Cup final — acquired Karlsson and made the 2019 final four, as the Swedish D-man recorded an impressive 16 points in 19 playoff games. Ahead of hitting the open market, Karlsson inked a massive eight-year deal to stay in San Jose.
However, things fell apart for San Jose the next season and Karlsson had trouble staying healthy. Though he did win the Norris Trophy in 2023, that marked his final campaign in Northern California. (More on that later.)
San Jose’s downturn meant one of the picks the Sharks sent Ottawa turned into third-overall selection Tim Stützle in 2020 and, seven years after the swap, the Sens are obviously thrilled to have Stützle at the top of their lineup.
Max Pacioretty to the Vegas Golden Knights, Sept. 10, 2018
Three days before Karlsson was sent to San Jose, the Montreal Canadiens traded their captain, Pacioretty, to the Golden Knights. As part of the move, Pacioretty inked a four-year extension with Vegas instead of becoming a UFA in 2019.
Things had grown contentious between Pacioretty and the Habs, as the Canadiens tried and failed to move the big winger around the 2018 draft. It’s believed Montreal initially targeted a young centre from Vegas, 2017 sixth-overall pick Cody Glass, but wound up with another pivot — Nick Suzuki, the 13th pick in 2017 — when the Knights wouldn’t include Glass in the deal.
You could sure slam a toe in the sliding doors here contemplating what life would look like in Quebec — and Vegas — had Montreal landed Glass instead of a future captain in Suzuki in the swap.
Pacioretty, like Karlsson, had all kinds of injury trouble with his new team and, after four years in the desert, he was on the move to Carolina before the contract he signed in Vegas ran out.
Nick Bonino to the Pittsburgh Penguins, July 28, 2015
One year after he was traded to Vancouver by Anaheim in the move that sent Ryan Kesler south, Bonino was packing his bags again, heading east to Pittsburgh.
Bonino, who scored 15 goals during his lone season in Vancouver, was traded for Brandon Sutter, who was bigger, one year younger and coming off a 21-goal showing with the Penguins. Sutter was entering the final year of his contract and the feeling was he’d eventually be due a raise the star-laden Pens likely could not afford.
Enter Bonino, who wound up being a dream fit behind Sidney Crosby and Evgeni Malkin as a 3C in Pittsburgh. He played two years in Pennsylvania, won two Cups and left as free agent in 2017. Bonino was particularly strong during the 2016 post-season, when he contributed 18 points in 24 games and averaged over 17 minutes per night for the Pens.
Sutter, meanwhile, was limited to 20 games during his first season in Vancouver and never again reached the 20-goal barrier.
Erik Karlsson to the Pittsburgh Penguins, Aug. 6, 2023
As noted earlier, things didn’t quite go the way Karlsson and the Sharks hoped when San Jose made a huge play to snag him in 2019. Still, Karlsson could be an offensive force when healthy and, in 2022-23, he put together the first 100-point season by a defenceman in the NHL since Brian Leetch in 1991-92.
With Kyle Dubas having taken over the GM reins in Pittsburgh in the summer of 2023, Pittsburgh tried to breathe new life into a bogging machine by acquiring Karlsson in a three-team trade with the Sharks and Canadiens.
For the second straight swap, though, Karlsson landed in a new spot just in time for the nosedive. Pittsburgh has not made the playoffs in his two seasons there and — like San Jose a few years ago — the Pens appear on the precipice of a full rebuild, which is why Karlsson (among other veteran Penguins like Bryan Rust) is back on trade boards in the summer of 2025.
Adin Hill to Vegas, Aug. 29, 2022
This certainly didn’t register as a significant swap when it was made, as Vegas sent only a fourth-round pick to get Hill from the San Jose Sharks. The Sharks — with James Reimer and Kaapo Kahkonen in the fold — had a crowded crease at the time and the 26-year-old Hill was the odd man out.
The big goalie had a total of only 74 career games on his resume to that point, though he’d certainly shown quality flashes in both San Jose and Arizona.
Hill played 27 games for Vegas in 2022-23, but wound up being the man in the playoffs, with both Logan Thompson and Laurent Brossoit battling injuries. Hill posted a .932 save percentage in 16 post-season games as the Golden Knights lifted their first Stanley Cup.
Yaroslav Askarov to San Jose, Aug. 23, 2024
When the Nashville Predators inked starter Juuse Saros to an eight-year extension on July 1, 2024, questions began swirling around the guy viewed as the top goalie prospect in hockey, Yaroslav Askarov.
Askarov was drafted 11th overall by the Predators in 2020, as high as any puckstopper had been taken since Montreal snagged Carey Price fifth overall in 2005.
But with his path to being an NHL starter apparently blocked long-term, Askarov reportedly requested a move. Shortly after saying the team expected Askarov to attend training camp, Nashville GM Barry Trotz sent the Russian to San Jose for fellow first-round pick David Edstrom.
Askarov, who turned 23 in June, played only 13 games for the rebuilding Sharks this past season, but figures to see his first year of real NHL action beginning in the fall.
Rutger McGroarty for Brandon Yager, Aug. 22, 2024
Last summer sure had its share of prospect drama. One day before Askarov was moved, the Winnipeg Jets found a solution to their Rutger McGroarty problem by trading the American forward to Pittsburgh for Brandon Yager. McGroarty had indicated he did not intend on signing with the Jets and would instead return to the NCAA for his junior year. Winnipeg waited for the right deal to come about, then collaborated with Pittsburgh on the one-for-one prospect swap.
The Pens could certainly be in the middle of another midsummer swap this year as we wait to see what they — and every other NHL club — might do to make this off-season interesting.
