NHL insider Bob Stauffer provided some intriguing insights into the contract extension negotiation talks of key Edmonton Oilers players, like Connor McDavid.On the Oilers Now podcast, Stauffer foresaw a scenario where extensions are completed by Aug. 28 for four notable players: McDavid, Mattias Ekholm, Jake Walman and Vasily Podkolzin."I'd say by August 28th with is a Thursday, a month from today, I could foresee a scenario where extensions are done on Podkolzin, Walman, Ekholm and McDavid. Seravalli and myself both said, you know, 100% Connor would re-sign, all along," Stauffer said.Stauffer noted that he and his fellow insider Frank Seravalli have long maintained that McDavid's re-signing with the Oilers was a certainty.Interestingly, Stauffer suggested that the timing of these extensions could be influenced by the upcoming wedding of Oilers superstar Leon Draisaitl, which is scheduled for late July or early August.“I could see some traction occurring after (the wedding). A potential extension for (head coach) Kris Knoblauch as well,” Stauffer added.Connor McDavid led the team to back-to-back Stanley Cup Finals appearances, falling short against the Florida Panthers. Securing McDavid's long-term future in Edmonton will be a top priority for the organization.NHL analyst speculates on Connor McDavid's message to OilersBryan Hayes suggested that Connor McDavid could be pushing the Oilers' front office to make more substantial roster improvements before he commits long-term to the team."Is it possible that he's gonna hold their (Oilers) feet to the fire?," Hayes pondered on TSN's "FanDuel Overdrive." (1:08:23)Hayes emphasized that while the Oilers haven't made significant changes, McDavid might be seeking a more tangible transformation to the roster before he's willing to sign a new contract.Hayes also noted that the Oilers' recent moves, like trading Sam O'Reilly to Tampa Bay and sending Viktor Arvidsson to the Boston Bruins, might not be enough to satisfy the superstar's expectations."I (McDavid) don't care that you changed the goalie coach, you got to, you better go find a new goalie before, out of principle, I'm not signing this until you do something tangibly different with this roster," Hayes speculated.As the offseason progresses, all eyes will be on the Oilers' front office and their ability to address McDavid's potential concerns.