The Edmonton Oilers raised some eyebrows around the NHL when they signed Trent Frederic to an eight-year contract extension worth $3.85 million per season. Despite Frederic's struggles after being acquired from the Boston Bruins, the Oilers are betting on his untapped potential and using the long term to secure a lower average annual value (AAV) in a rising cap environment. The Oilers hope the 26-year-old Frederic can effectively fill the void left by Evander Kane, banking on his potential to return to his 20-goal form he flashed in Boston. This strategy of locking in depth players early with team-friendly contracts may extend beyond Frederic, with three other Oilers potentially in line for similar deals: Jake Walman, Vasily Podkolzin, and David Tomášek.

Jake Walman: Top-Four Stability at a Predictable Price

Rumors are circulating that the Oilers are considering an eight-year extension for defenseman Jake Walman. Walman, who was acquired at last season's trade deadline, has impressed with his skating, puck-moving abilities, and capacity to handle tough minutes. At 29 years old and entering the final year of his $3.4 million deal, this could be his best opportunity for long-term financial security. Bob Stauffer, an insider, has suggested that the Oilers might leverage their exclusive right to offer an eight-year term before free agency, especially with a new CBA on the horizon. Such a deal, potentially around $6 million AAV, would provide the Oilers with cap certainty for a key defenseman as they prepare for major extensions with Connor McDavid and Evan Bouchard. While some believe that giving a defenseman of Walman's age an eight-year deal is a stretch, the Oilers may be hoping to lower the annual cap hit to make him affordable.

Vasily Podkolzin: A Bargain in the Making

Vasily Podkolzin might be the Oilers' most underrated breakout candidate. At just 24 years old and with a $1 million contract, Podkolzin offers significant potential. While his offensive numbers may not yet be eye-popping, his underlying metrics suggest he could blossom into a valuable top-nine forward. If Podkolzin can develop into a consistent scorer, an eight-year extension at a reasonable AAV could be a steal for the Oilers.

David Tomášek: High-Upside Winger

David Tomášek is another player who could benefit from the Oilers' long-term vision. The 27-year-old winger has shown flashes of offensive brilliance and possesses a skillset that could translate well to the NHL. While he lacks extensive NHL experience, Tomášek's potential is undeniable. By offering him an eight-year deal, the Oilers could bet on his upside while maintaining cost control.

The Oilers' willingness to offer eight-year extensions to players like Frederic, Walman, Podkolzin, and Tomášek reflects a strategic approach to team building. By locking in these players at potentially team-friendly AAVs, Edmonton aims to create a competitive roster while navigating the complexities of the salary cap. This strategy carries risk, as the performance of these players over the contract's duration remains uncertain. However, if the Oilers' gambles pay off, they could be well-positioned for sustained success.