The Edmonton Oilers Have a Growing Connor McDavid Problem

Pity the poor Edmonton Oilers fan.

Not only have they endured consecutive Stanley Cup Final losses to the same southern state foe whose mere mention may inspire night terrors, but the months since loss No. 2 have been pockmarked by social media trolling from their Cup-toting conquerors.

Conn Smythe winner Sam Bennett was the latest to rip at the competitive scab, co-opting trophy babysitter Philip Pritchard's account on X last week to post a wake-surfing video while the boat in front of him blasted Edmonton's locker-room anthem "Pink Pony Club."

It was an irritatingly incendiary reminder of two foiled playoff runs.

But given what could be on the Oilers' doomsday horizon, it barely registers.

Because the team is just 25 days away from opening night of its preseason schedule and the on-ice start of what could be Connor McDavid's final season in blue and orange.

Yes, you read that correctly.

The five-time scoring champion and three-time MVP, who signed an eight-year deal with Edmonton in 2017 at the bargain-basement annual rate of $12.5 million, has not re-upped in the eight weeks since the team's window opened to negotiate a new extension.

Which may already, depending on one's level of northern Alberta zeal, be prompting everything from an elevated heartbeat to a training run through the seven stages of grief.

The latest cause for anxiety came Wednesday, when, sitting at a pre-Olympic press conference alongside prospective Canadian teammate Sidney Crosby, McDavid was asked to discuss the timing of negotiations and whether he believed GM Stan Bowman had done enough in the summertime to secure a commitment before the season starts.

And instead of the instant "yes" that would have dialed the panic meter back a few dozen notches, the now-28-year-old captain dove back into the cryptic pool he'd entered in late June when saying he'd "need to do what's best for me and my family."

In fact, this time he not only held his "I'm being patient" ground, he fortified it.

"I would say all options are on the table, really," McDavid said. "We're going through it. I don't have a preference either way. … I'm taking my time with it, and that's it."

The words, and the detached, slightly irritated way he delivered them, were enough to make current season-ticket holders squirm in their Rogers Place seats—and give at least some pause to anyone perusing a rack full of pricey No. 97 merchandise.

For the youngsters in the crowd, it's the first time around such concern.

But for those Oilers fans with some miles on them, it's eerily reminiscent of 37 years ago this month, when then-owner Peter Pocklington pulled the pin on a transactional grenade that sent the franchise's first preeminent player, Wayne Gretzky, to Los Angeles just a few weeks before No. 99 entered the final year of a long-term contract.

The team won its only post-Gretzky Cup in 1990, made two more playoff runs on institutional muscle memory, then plummeted into a chasm of 15 playoff misses in 22 years before McDavid arrived as the No. 1 overall pick in 2015.

Before we get too immersed in doom and gloom, though, not all the current news is dire. McDavid also said that he "has every intention to win in Edmonton".

"That's my only focus. Maybe next to win the gold medal with Canada, but it is my intention to win [in Edmonton].

Plenty of people who know what they're talking about believe an agreement will come sooner or later, including The Athletic's Pierre LeBrun, who suggested there's a "good chance" McDavid signs an extension for a term shorter than the max eight years.

And veteran insider Frank Servalli took to a B/R Open Ice live stream to forecast a four-year deal with an annual value somewhere between $16 million and $17.5 million that'll get done "the minute that Connor McDavid picks his head up off the pillow and decides that he would like to have a contract extension done."

It's the latest reason why Bowman's not getting much sleep.

His first full Oilers offseason has already been nothing if not eventful, with extensions done for Evan Bouchard and Trent Frederic, a trade that sent Evander Kane to Vancouver and the signing of free-agent Andrew Mangiapane to offset the free-agency departures of veterans Corey Perry and Connor Brown.

He also swung a deal to acquire Hobey Baker Award winner Isaac Howard from Tampa Bay, which, along with promotions for fellow 20-something farmhands Matthew Savoie and Noah Philp, adds a youthful jolt to a roster that entered last season as the league's oldest.

But it hardly means the pressure is off.

If he hasn't signed, McDavid's "all options are on the table" remark ramps up the necessity for the team to be contention-ready from the jump, lest he genuinely begin thinking about leaving.

Of course, there's no reason to believe the two-time defending conference champs won't again be a power out West, but the hurdles are many in places like Vegas, Dallas and Colorado, there's still been no seismic change to an iffy goaltending situation and vital pieces Zach Hyman and Ryan Nugent-Hopkins are closer to their ends than their starts.

If Edmonton stumbles from the gate like the last two seasons—5-12-1 in 2023-24, 6-7-1 in 2024-25—or, gasp, finds itself out of the playoff picture for a prolonged stretch, would Bowman consider a blow-it-all-up trade that'd leave Leon Draisaitl, who signed an eight-year extension last September, to soldier through a rebuild alone?

Or would he risk riding it out with McDavid and losing him for nothing next July?   

Simply put, the best tonic to entice their star to stay is win and win often.

But until the deal is done, there'll be plenty of angst to go around.