Connor McDavid and Auston Matthews.

Two long-time friends, fierce competitors and players who will forever be intrinsically linked as franchise players who helped usher in this latest generation of elite hockey players.

Drafted first overall a year apart — McDavid in 2015 by the Edmonton Oilers and Matthews in 2016 by the Toronto Maple Leafs — fans have always wondered what it would be like to see them on the same team. And while they got a taste of it at the 2016 World Cup of Hockey when they joined forces on Team North America, there’s always been a curiosity about them being on the same NHL team.

With McDavid’s two-year extension set to expire after the 2027-28 season, the same year that Matthews’ current $13.25-million deal expires, both have the chance to enter unrestricted free agency at the same time as Columbus Blue Jackets defenceman Zach Werenski.

All three are represented by Wasserman’s Judd Moldaver, who joined Sportsnet’s Elliotte Friedman and Kyle Bukaskas on the 32 Thoughts podcast, where he was asked about two of the three potentially playing on the same team.

“I know it’s a two-way street when they’re competing against each other, either international or in (NHL) games. It’s all about winning,” he said of McDavid and Matthews, specifically. “That’s just too far in the future. You know, it so happens, I guess, that they’re all UFA the same summer. What the future holds, I don’t know.”

Werenski, drafted eighth overall in the 2015 draft by the Blue Jackets, is much like McDavid and Matthews in that he has only played for one team throughout his entire career, a situation Moldaver said he would ideally like to see for all three.

“I think I can clearly say for all three of them: they love their organizations, the Leafs, the Jackets, the Oilers, respectively,” Moldaver said. “And for them it’s winning where they’re at and in all three cases have only played for one organization.

“And if they can continue on in a good light there and have a chance to win, hopefully they all stay where they are. I think that’s sort of the easy target that they’re all UFA the same summer is again, I guess an interesting scenario. But what the future holds, I don’t know.”

Much like McDavid and Matthews, Werenski has catapulted himself to being one of the best at his position in the league, racking up 23 goals and 82 points in 81 games last year amid a breakout campaign. When that summer hits, Werenski will be coming off a six-year, $9.583-million deal, and as is the case of the other two, will be in line for a pay raise in this world of a rising salary cap.

Zach Laing is Oilersnation’s associate editor, senior columnist, and The Nation Network’s news director. He also makes up one-half of the Daily Faceoff DFS Hockey Report. He can be followed on X at @zjlaing, or reached by email at zach.laing@bettercollective.com.