Michael Traikos and Jacob Stoller discuss whether this was Connor McDavid's one-and-only chance to win the Stanley Cup or whether the best is yet to come. Leon Draisaitl [https://thehockeynews.com/.image/c_fit,h_600,w_600/MjA3OTQzNzMxMDc1MDk4Mzcz/usatsi_23609635_168400847_lowres.jpg] Leon Draisaitl Right until the Edmonton Oilers sign or don't sign Leon Draisaitl, the rumors and speculation will continue. The star forward's agent seems confident Draisaitl's staying put [https://thehockeynews.com/nhl/edmonton-oilers/latest-news/either-it-happens-quickly-or-doesnt-happen-at-all-leon-draisaitls-agent-gives-thoughts-on-contract-extension], but talk about the term has varied. The Fourth Period's Dave Pagnotta speculated on Sunday that Draisaitl might favor a three- to four-year contract extension over locking into an eight-year deal. This development contrasts earlier speculation from Bob Stauffer of Oilers Now [https://x.com/timminstoilets/status/1801809881382445171], who indicated Draisaitl was not seeking an Auston Matthews-like deal of four years. On the surface, this sounds like a less-than-ideal pivot for Oilers fans, but is it really? If this shorter-term extension materializes, it could benefit Draisaitl and the Oilers. THE POSITIVES OF A SHORTER-TERM EXTENSION By opting for a three- to four-year extension, the Oilers avoid the potential financial burden of locking in Draisaitl at a likely astronomical figure for an extended period. Given Draisaitl's projected market value of $13 million to $14 million per season, an eight-year deal would be a significant long-term commitment. A shorter contract allows the Oilers to maintain flexibility in their salary cap structure, making it easier to adapt to changes in player performance and league economics. Typically, players allow some cap-hit discount for longer extensions, but it's unlikely the Oilers would save all that much if they tried that on a superstar such as Draisaitl. A shorter deal also enhances Draisaitl’s tradeability if the two sides look for a change of scenery later, providing the Oilers with an invaluable strategic asset. Should the team’s circumstances change or if they must address other roster needs, Draisaitl's shorter contract would be more attractive to potential trade partners. The reduced term mitigates the risk for other teams, making it easier to negotiate a mutually beneficial deal if necessary. KEEP DRAISAITL IN HIS BEST YEARS If the Oilers' best chance to win the Stanley Cup is within the next three to four seasons while the core is in its prime, signing Draisaitl beyond that ideal window should only be if the player demands it. If he wants eight years as a pending UFA, the Oilers may have to offer it to keep him from leaving. That said, Draisaitl’s peak performance aligns with a shorter timeline, and a four-year extension ensures that the team can maximize his productivity. After the 2024-25 campaign and the four seasons that follow, he can hit free agency again. Edmonton shouldn’t be phased by that idea when he is 33 years old. By then, he may be at an age where a shorter term allows for re-evaluation and adjustment as the NHL’s salary cap evolves. WHY WOULD DRAISAITL AGREE TO A SHORTER TERM? From Draisaitl’s perspective, a longer-term offers the most stability, but a shorter deal also has its merits. Draisaitl would still be within an age range where he can command a substantial contract if his production remains elite after three or four years. This setup allows him to potentially benefit from an increased salary cap, positioning himself for another lucrative deal when he’s still an effective player. By the time his next extension comes around, he’ll then be where Steven Stamkos was this summer – stay with the same team or leave in free agency for another mid-term deal for potentially better money. A shorter term allows him to choose his next destination based on his career goals and the NHL’s financial landscape. Get the latest news and trending stories right to your inbox by subscribing to The Hockey News newsletter here [https://info.thehockeynews.com/mail/microsites/951/1/gTeQVf?_gl=1*ustlbj*_ga*NjkyMzUxMy4xNjYzNjIwMzQ3*_ga_PK63FB1PME*MTcxMzUwOTExNi40NDguMS4xNzEzNTA5MjA5LjU5LjAuMA..].
