Oilers alumni question Connor McDavid's intention with potential Lebron James-esque two-year contract extension 

Connor McDavid has yet to sign a contract extension with the Edmonton Oilers. The forward has been eligible to sign one since July 1, having entered the final year of his current eight-year, $100 million contract. While there are indications that he will re-sign with the team, there are doubts over the length of the contract.

In eight years, the Oilers have failed to land the Stanley Cup despite having the likes of McDavid and Leon Draisaitl. They have come close the previous two years, but both times the Florida Panthers' depth has outnumbered them.

They have locked in Draisaitl through an eight-year, $112 million extension that will start from this year. But while McDavid and Draisaitl remain close, there have been expectations that the Oilers captain will sign for a shorter-term contract.

On Thursday's episode of TSN's "Overdrive," Jim Tatti, Jason Strudwick and Dave Feschuk discussed the possibility of McDavid pulling off a move like LeBron James, who is known to not commit to a team long-term to maximize chances to win. LeBron has had past contract spells of a similar nature with the Cleveland Cavaliers and Los Angeles Lakers.

Former Oiler Strudwick pointed out that the short-term deal is expected to motivate the team to win.

"Oh, yeah. And I understand it. Like, I get where that's coming from, but I mean, why wouldn't you try to win when you have LeBron or Connor McDavid? I don't really understand that logic. Maybe the other people have suggestions of or examples of players that have been misused by teams," Strudwick said (Timestamp- 3:50 onwards).

When Feschuk said there must be alternatives if Edmonton can't win, Strudwick added it is hard to guess where a player like McDavid can go to guarantee team success.

"Maybe they can't win, Strudwick. Maybe that's the thing, like if he can't win here, maybe he's got to go somewhere else," Feschuk said.

"But then, where is that? I think that's a hard game to play, too, right? 'We're going to go here,'" Strudwick added.

Oilers or Connor McDavid shouldn't be worried about signing long-term, per NHL analyst

According to The Athletic's Allan Mitchell, signing Connor McDavid to a long-term extension will not put any added pressure on the franchise. With the team they have, they are expected to support their captain for at least a decade to come.

"That inevitability means an eight-year deal is far more likely to secure a decade of brilliance. ... Instead of worrying about regression, Oilers fans should see such a contract as great news, a commitment that ensures the NHL's most dominant player remains in Edmonton through his prime and beyond," Mitchell wrote.

A not-so-dissimilar situation played out in Pittsburgh, where Sidney Crosby and the Pittsburgh Penguins aren't competitive near the twilight end of his career. But the Oilers can hope for a positive outcome instead because of how their organization has built the team around McDavid.