The Edmonton Oilers made a move this offseason that screams “Connor needs to stay here”. 

Joining the Oilers organization is Jeff Jackson, the now former player agent for Connor McDavid. Jackson changes his hat, going from getting McDavid the best deal for the player, to working on keeping Edmonton’s captain in Oil Country. McDavid has three years left on his contract. Jackson will report directly to Oilers owner Daryl Katz. 

Welcome, Jeff Jackson! 🤝 pic.twitter.com/RS5dnY3Ree

— Edmonton Oilers (@EdmontonOilers) August 3, 2023

But what about his other clients? What happens to them? Well, his former agency will take over representing them. But they will need to work hard at retaining those clients.

For those curious… With Jeff Jackson having left Wasserman to join the Oilers, I believe all of his clients are staying with the agency, led by their now 3 EVPs.

— David Pagnotta (@TheFourthPeriod) August 3, 2023

But back to the Oilers,

Hiring Jackson is clearly a strategic move aimed at facilitating the process of re-signing McDavid when his contract comes to an end. Bringing in the man who has worked with him the longest and knows what should motivate their star player to remain. This is an intelligent hire on the Oilers’ part, especially as retaining the NHL’s best player should be their top priority, especially if they want to keep their Stanley Cup window open. 

This move carries several potential benefits for the Oilers: 

Knowledge:

By hiring McDavid’s agent, the Oilers gain access to insider knowledge about the player’s preferences, goals, and concerns. Someone who has been working closely with McDavid and understands his desires both on and off the ice. This insight should allow the Oilers to tailor their contract negotiations to align with McDavid’s priorities, increasing the likelihood of a successful extension.

Trust:

McDavid has developed a strong working relationship with Jackson who has proven his ability to handle McDavid’s career and contractual matters effectively, and in a way that his client approves of, earning McDavid’s trust in the process. By adding McDavid’s trusted former representative in any future negotiation process on the side of management, the Oilers can more easily build a sense of familiarity and comfort, creating a positive atmosphere for contract discussions.

Market Value:

Having been one of hockey’s top player agents, Jackson is well-versed in the current market trends and player valuations within the NHL. Because of that, he should also be capable of staying up to date on those values, and capable of better projecting, especially in the long term, with access to NHL data. Walking the tightrope of being able to offer McDavid his full market value, likely as the highest-paid NHL player at that time but offering him something else he values to provide stability for him taking slightly less.

Conflict Mitigation:

Negotiating player contracts can be the most time-consuming, complex, and emotionally charged part of the general manager’s role. With Jackson on hand as the part of the organization that gets the final decision (outside of the team owner), the Oilers can minimize potential conflicts and miscommunications that may arise during the upcoming negotiation process. Jackson could even step in if the negotiations become too adversarial, and act as a mediator between McDavid and the team. Jackson could guide the discussion in a direction McDavid’s camp would be comfortable with and remain amicable with the club.

Most importantly for Oilers fans, Jackson’s appointment certainly can’t hurt Connor McDavid’s long-term future in Edmonton. McDavid has three years left on his contract.

2/2

— Daniel Nugent-Bowman (@DNBsports) August 3, 2023

Commitment:

The decision to hire Jackson showcases the team’s commitment to their star player. It sends a strong message that the organization values McDavid not just as a player but also as a long-term partner in their goal of winning a Stanley Cup, something that McDavid himself has stated is his only professional goal remaining for him to achieve. This hiring may foster a positive and respectful relationship between the player and the team, adding to the likelihood of a contract extension.

It’s clear that the Oilers have made this hiring in the hopes of positioning themselves favorably to secure a long-term contract with their franchise player. Which only makes sense as whatever McDavid decides will impact the Oilers’ hopes of retaining other stars such as Leon Draisaitl and Evan Bouchard, which will ensure they are placing a contending team on the ice but also, ensures the long-term financial stability of the franchise providing the best quality possible to a hockey-mad city.