Connor McDavid Contract Rumors (Getty Images)Connor McDavid's contract future continues to fuel discussion across the NHL, but not every theory is gaining support from those closest to the Edmonton Oilers. Fresh speculation suggested the superstar could command between $23 million and $25 million annually on his next deal, with some even floating the idea of a $200 million contract. While those numbers grabbed attention, Oilers insider Jason Gregor believes they ignore one key factor that has defined McDavid's career. In Gregor's view, the captain's priority has never been squeezing every possible dollar out of a contract. Instead, he believes McDavid is focused on giving his team the best chance to compete for the Stanley Cup.Why does Jason Gregor believe Connor McDavid won't chase a $23 million salary?The latest round of speculation began on the Spittin' Chiclets podcast, where Ryan Whitney argued that the NHL's rising salary cap and McDavid's unmatched production could justify an annual salary between $23 million and $25 million. Paul Bissonnette took the conversation a step further by suggesting a deal worth roughly $200 million.Gregor was not convinced.Rather than focusing on what McDavid could earn, he pointed to what such a contract would mean for the team's ability to contend.“You think Conor McDavid is going to go and try to get $23 million? So if Conor McDavid hasn’t won a Cup in two years, and his contract’s up, you think he’s going to want to go get as much as he can? Because that will just lower his chance of winning. It makes no sense,” Gregor said.He continued by explaining why he believes the Oilers captain thinks differently from many other stars.“From a pure rational thought process, McDavid wants to win. Taking 23 million? Not going to do it. Whether it’s in Edmonton or anywhere, he’s not going to do it. Because he wants to win. And he knows if he takes up too much, his chance of winning is less. It’s just how it goes,” he added.Gregor's argument also lines up with McDavid's latest contract decision. In October 2025, the Oilers captain signed a two-year, $25 million extension that kept his annual cap hit at $12.5 million instead of pushing for the highest possible salary. The move gave general manager Stan Bowman additional room to strengthen the roster around McDavid and Leon Draisaitl during a critical championship window.What could Connor McDavid's next contract look like after 2028?The two-year extension means McDavid's long-term future will again become one of the NHL's biggest stories in 2028.Edmonton has spent this offseason trying to justify the flexibility McDavid gave the organization. Following a disappointing first-round exit against the Anaheim Ducks after consecutive Stanley Cup Final losses to the Florida Panthers, the Oilers reshaped several areas of the roster.The club replaced Kris Knoblauch with Mike Babcock behind the bench, looking for a more demanding, structured approach. Bowman also created valuable salary cap space by moving Darnell Nurse to the San Jose Sharks without retaining salary. Edmonton then addressed its goaltending by signing Stanley Cup winner Frederik Andersen and acquiring young goalie Devon Levi from the Buffalo Sabres.Those moves have strengthened the roster on paper, but the real test will come once the season begins.If the Oilers finally capture the Stanley Cup before McDavid reaches free agency again, a long-term extension in Edmonton would appear to be the natural outcome. With the league's salary cap expected to rise, an annual value somewhere in the $16 million to $18 million range seems more realistic than the figures currently making headlines.If another championship opportunity slips away, however, McDavid could enter unrestricted free agency at age 31 with every option available to him. Until then, Gregor believes McDavid's recent decisions already reveal what matters most. Winning has consistently come ahead of setting a new salary record, leaving the Oilers with the responsibility to prove that sacrifice was worthwhile.