This feels like the NHL’s version of “The Decision,” albeit almost certainly without a TV special when the announcement of a new contract — and perhaps even a next team — finally comes.

There are many parallels between Edmonton Oilers captain Connor McDavid entering a contract year and NBA superstar LeBron James hitting the open market more than 15 years ago. Both generational athletes are and were at the peak of their powers. Both competed in at least one championship series, but both are or were without a ring. Both are and were on teams vying for a title in the immediacy, but facing potentially questionable longer-term futures.

There’s a lot for McDavid to weigh as he ponders the prospects of playing for the Oilers past this season. He can sign a lengthy extension, commit for just a bit longer, see what else is out there next summer, or even go for “no term” — as he suggested earlier this month — and take his talents elsewhere.

With such an important decision looming not only for just McDavid but also for the Oilers, the league and his peers, The Athletic canvassed 10 player agents to get their thoughts. Receiving anonymity to speak freely about someone who isn’t their client, the agents were posed a simple question: “What would you advise Connor McDavid to do?”

Decision-making process

Agent 1: “What he’s telling everybody is, ‘I want to win here with my friends.’ Makes sense. The problem is, ‘I don’t know that I can.’ At least, I believe that’s the issue.”

Agent 2: “I get the sense he is conflicted and simply needs more time.”

Agent 3: “If Connor takes a short-term deal, it’s for a couple reasons: to see if they can win in three years and then go elsewhere as well as leave a bit of cap space for the team to work with. The cap will go up enough that it will make a difference on the AAV as well as maximizing the number of contracted years.”

Agent 1: “When Connor McDavid looks at a new team, he needs to make sure they can answer one question: When players become unrestricted free agents, will they want to play here for less? That’s what’s happening in Vegas, Tampa, Florida, maybe a little bit in Dallas. If they’re getting players at 20 percent discounts, how do you compete? If you’re the Edmonton Oilers, it’s challenging.

“I’d have a lot of analytics done. I’d take a leadership role. Think of Kobe Bryant, who I admire as one of the greatest. He wouldn’t pass the ball to a guy that he didn’t think would work hard. He wasn’t going to let his legacy be interrupted by a guy who didn’t want it as bad as he did. He just quit passing the ball to him and went up to Jeanie Buss and said, ‘You’ve got to get him out of here.’

“My advice to Connor would be to take the ball and run with it, and really make sure that your team is helping you to make this decision. You’ve got to make an informed decision that, to some degree, identifies the probabilities of you accomplishing your goal wherever you decide to go.”

Agent 4: “Unless the Oilers give you everything you want now regarding term and money, playing out the season on the expiring contract may be the best strategy. You’ll be in a better position to assess the Oilers’ Stanley Cup chances and also have a better idea of which other teams are emerging as Stanley Cup contenders.

“With the upcoming increases to the upper limit (of the salary cap), there will be no shortage of teams that will be able to afford to sign you, and there is a very good chance this will be your last opportunity to sign a contract while in your prime — unless you decide to go very short.”

Agent 5: “A player of McDavid’s stature as the best player in the world could have just one opportunity to become an unrestricted free agent in the prime of his career. This is his right under the CBA. He’s already achieved generational financial security. McDavid can make a decision on his next contract based on his own individual priorities. He may value signing with a contending team, composition of the coaching staff, projected linemates, the city, the income tax situation, family considerations or any other criteria.

“Why wouldn’t he play out the season to get a peek around the curtain and see what his options are for what comes next? Edmonton is there now and will certainly be there on July 1, 2026.”

Contract length

Agent 1: “I think it’s probably a short-term deal. If it’s a short-term deal, one, two or 10 teams can start planning for it (next time).”

Agent 4: “Salaries for high-end forwards are about to explode, and while a short-term contract could take maximum advantage of that, keep in mind that you will be turning 33 during the first year of a new contract if you sign a three-year extension now. Once Sept. 15, 2026, arrives, there will be no more eight-year contracts, so the key calculation is which of the three scenarios maximizes your earnings: two or three shorter contracts; go long now and then short; or go short now and then long.

“Of course, having the ability to choose where to play can be just as valuable as maximizing your earnings and going short may be more attractive for that reason.

Agent 5: “My last piece of advice is to think short-term on any new deal. There will be pressure to do four or five years, but I would strongly advise no more than two years. Why not have the opportunity to re-evaluate everything again? If things are working out great and he’s happy where he’s at, do another short-term deal. If he would like to be somewhere else, that option will always be open to him as well.”

Agent 6: “He should do a two- or three-year term and put the pressure on Oilers management and ownership to surround him and Leon (Draisaitl) with good players. This way, with the cap going up, he buys him and Leon a few more years to get it done as a pair of top-five forwards in the league. If at the end of that term he doesn’t want to stay, he can sign a max ticket elsewhere, and the Oilers would have had him for 13-plus years in his prime and unable to get it done.”

Salary

Agent 7: “If I was representing him, this player would be the highest-paid player at the max contract. Less than that? That’s a non-starter.”

Agent 8: “I am not one to second-guess other agents’ strategies, but it’s pretty clear that Edmonton has just given him a blank check. McDavid has earned the luxury of waiting to decide what he wants to do. His market value isn’t going down, so there is zero risk to waiting.”

Agent 7: “For term and for how long? I don’t know because that’s where it’s with McDavid on whether he’s prepared to leave Edmonton. Being the highest paid player, max contract, for whatever the max will be a year from now, is automatic. He owes that to himself and to all the players to drive the bar as high as possible in a rising cap system. End of story. If he was my client.

“It would be starting at $20 million. A team has $100 million to spend (next season). To me, this goes back to the days of Gretzky, Lemieux — the best players in the game should be the highest paid. That’s important. He has earned enough money in his career to absolutely play out this season and then decide at the end of the year what he wants to do.

Agent 8: “The only thing I might do differently is to release a statement saying that he won’t be commenting on contract negotiations during the season and is focused exclusively on winning the Cup this year.”

Agent 7: “So take as long as you want to decide and understand your obligation to yourself and the rest of the players to earn as much money as you possibly can. And a smart team will build around the best player in the world.

“He has that ability to do (a short-term deal now). He’s earned his $100 million. So he could bank a two-year, $40 million contract and see how it goes. God bless him. Why not? If that’s what’s important to him. He has maximum flexibility to do whatever he wants because that guy has earned it and deserves it, and everybody should respect it so long as it’s a max deal.”

Determining the Oilers’ future

Agent 9: “My advice would be to start the season, and really assess if the club is going in the direction he wants, sit with management and hear the plans, and then weigh being the highest paid player in the league in another city, or stay and maybe structure a shorter deal that gives another chance of winning a Cup in Edmonton. I’m assuming that his management team is looking at any and all tax language, deal structure and estate planning to maximize the most net dollars they can for their client, while weighing off-ice endorsement revenue in Edmonton versus other markets.”

Agent 1: “I would also evaluate the chances of winning in Edmonton. I’m not so sure, all things being equal, that he doesn’t have as good a chance there as anywhere else.”

Agent 2: “He controls the process completely and should wait until June so he gets a clear picture of the Oilers’ status as a contender and knows all his potential options before making a final decision.

“Teams make players wait 99 percent of the time; this time, the leverage and status dictates that the team must wait.”

Agent 1: “My advice to him would be to seek out some experts in predictive analysis — and there are some of them that have done some work in hockey — and do the best you can to make more than a gut call. This is a big decision. I would approach it like a Fortune 500 company.

“He’s got to hire a group of people with experience in analyzing what it takes to win. He’s said he wants to win multiple Cups — as many as he can. The reality is, if you study dynasties, they don’t usually set out to win (just) one. You need a team with a committed vision to win multiple Cups. If I’m him, I’m going to find out where that is.”

Legacy

Agent 10: “Connor McDavid is widely recognized as the most talented hockey player of his generation, a once-in-a-lifetime athlete whose speed, vision and skill put him on a level few in NHL history have reached. Yet, as extraordinary as his personal achievements are, hockey is ultimately a team sport. Even the best player cannot win a Stanley Cup on his own. This is why I believe McDavid should consider signing a team-friendly contract, much like Sidney Crosby did with the Pittsburgh Penguins, to give the Edmonton Oilers their best chance at building a true championship roster.

“Crosby set an important precedent when he signed a long-term deal that paid him less than the maximum he could have earned. His reasoning was simple: By leaving money on the table, Pittsburgh could surround him with the depth needed to win. The result was three Stanley Cups, cementing Crosby’s legacy not just as a generational player, but as a proven champion.

“McDavid faces a similar opportunity. While he deserves every dollar he could command on the open market, slightly reducing his cap hit could free up millions of dollars for Edmonton to strengthen its defense, add goaltending stability and create a balanced lineup capable of competing with the league’s deepest teams.”

Agent 1: “This is way more complicated than people realize. This is life-defining and legacy-defining for him.”

Agent 10: “Winning in today’s NHL is about more than one superstar carrying the load. The salary cap forces difficult trade-offs, and teams with multiple stars on maximum deals often struggle to keep the supporting cast intact. McDavid has already secured financial stability through previous contracts and endorsements, but his legacy will ultimately be defined by championships.

“By choosing a team-friendly deal, he could ensure that his prime years are remembered not only for jaw-dropping highlights, but also for lifting the Stanley Cup.”

(Photo: Jason Franson / The Canadian Press via AP)