July 1 isn’t just an important day on the NHL calendar for the 2026 free agent class — it’s also the first day 2027 free agents are eligible to sign extensions.The market is changing in a rising-cap world. Salaries are trending up. So is player movement, with an uptick in trades in the early phases of the offseason. Some of that’s fueled by more empowerment, with players starting to take control of their futures.As much as the environment evolves, one thing is likely to stay the same: teams taking a proactive approach with star talent.Few franchise-caliber players actually make it to unrestricted free agency. Connor McDavid, Kirill Kaprizov, Jack Eichel, Artemi Panarin, Martin Necas and Kyle Connor headlined the 2026 class, but not one will be available this year on July 1. In 2025, Leon Draisaitl, Mikko Rantanen, Sidney Crosby, Shea Theodore, Victor Hedman, Jaccob Slavin and Igor Shesterkin, among others, came off the board early too.Teams generally try to take a proactive approach with their stars to 1) negotiate before market trends push costs to a new level, and 2) gain certainty around their top players and salary-cap outlook.When players don’t express interest in extending beyond the next season, it gives general managers time to start planning for that eventual exit. Any trades involving those players can still lead to an early extension. Kiefer Sherwood extended a few months early in San Jose after being traded from Vancouver. Rantanen signed an extension when Dallas acquired him at the deadline last year.So it’s already time to look ahead to the 2027 class. What could those contracts look like? Keep in mind, there’s one catch unique to this season: if any players want an eighth year on their deal, it has to be signed before the new CBA kicks in in September 2026. The maximum will be capped at seven years moving forward.Winners and losers from the 2026 NHL DraftScott WheelerCale Makar, Colorado AvalancheThe 2027 free-agent class is headlined by a lot of star power, including two of the best defensemen in the world. Makar and Quinn Hughes are unicorns and could reset the defense market with their next contracts, with deals in the echelon of other MVP-caliber players. Whoever signs first could set the tone for the other.The intention, according to president and general manager Joe Sakic, is to get a Makar extension done this summer. With a statement like “Cale is going to finish his career here” after the season ended, a maximum deal could be on the horizon.The cost is where things get really interesting, because the cap is projected to rise to $113.5 million in Year 1 of his next contract and he’s worth every penny he could ask for. When accounting for that year-to-year cap growth, Makar is projected to be worth over $20 million-plus per season on an eight-year deal. Between his elite game, rising costs around the middle class and this empowerment era, Makar could push for that.But stars generally sign below their market values. Nathan MacKinnon did just that on his last contract in Colorado, so maybe it sets a precedent for his teammate. MacKinnon’s $12.6 million AAV took up 15.1 percent of the cap during its first season in 2023-24. That equates to $17.1 million in a $113.5 million cap. But Makar could sign for even less than that; AFP Analytics projects a slightly more down-to-earth cap hit of $15.1 million.Quinn Hughes, Minnesota WildWith the Kirill Kaprizov contract, which carries a $17 million AAV, the Wild have already shown a willingness to invest heavily in their stars. Hughes could ask for the same amount — he’d be worth it, with a projected market value of $18 million over the next eight years. It’s just a dramatic leap, which is more than double his current earnings.Consider $18 million the ceiling, unless Makar signs first and sets the bar higher. While the dollars and cents are the bigger variable for Makar, the term may be for Hughes. If he doesn’t push for a maximum value contract in length, maybe that betters his chances of signing closer to his market value, with a $17-18 million cap hit.While that contract would age better, there would still be risk from the Wild’s side of the equation. Say Hughes pushes for a three-year deal that allows him to cash in for one more splashy contract; that would line up with his brother Jack Hughes hitting the market at the same time. After investing so much in bringing in a true No. 1 defenseman, and this window overall, Minnesota may want a little bit more security. The Wild’s chances of winning may be in the front half of his next contract, with their core ages in mind, but a five-year window is obviously more ideal. That would be the most fitting middle ground here, no matter the cost.Nikita Kucherov, Tampa Bay LightningWhile the Lightning weren’t willing to sign Steven Stamkos early and ultimately let him walk as a free agent, the team did sign the rest of its core players a year early. Kucherov, Andrei Vasilevskiy, Brayden Point, Victor Hedman and Brandon Hagel all had extensions in place a full offseason before their last contracts expired. So it wouldn’t be surprising to see management take that same route with its most valuable player.