The Edmonton Oilers are in the Stanley Cup Final once again and facing the Florida Panthers. While everyone in Alberta focuses on bringing the title back, it's never too early to peek ahead to the summer. The Oilers should supplement their core in NHL free agency, but only after signing Connor McDavid to a long-term contract extension. Failing to lock in McDavid now would cause the entire summer to be a failure, regardless of their other pickups. The dream is signing McDavid and adding around him to create a sustainable champion.
The Oilers have already locked in Leon Draisaitl for eight years at $14 million annually starting on July 1. Before any extensions or free-agency deals are signed, Draisaitl is set to be the highest-paid player in the league. McDavid should smash his teammate's record, which will make it hard for Edmonton to have elite depth under the salary cap. But three regular-season MVPs and a Conn Smythe Trophy before turning 29 warrant the big pay day.
There is no drama around McDavid and the Oilers right now. He is the captain of the team, his friend has already been taken care of, his junior coach is the head coach, and his former agent is the president. McDavid leaving would be nothing short of stunning, as there have been no rumors about his unhappiness yet. But there is no reason to leave it up to chance. Stan Bowman should make McDavid the highest-paid player in the league on July 1, when he is eligible for an extension.
The Oilers will still want to improve this summer, even if they win the Stanley Cup. How can they do that with Draisaitl and McDavid taking up so much of the cap? Finding the right bargain moves in free agency will be key this summer.
The Oilers' dream continues with depth additions and another extension

The biggest free agent on the Oilers' books this offseason is defenseman Evan Bouchard. He is a restricted free agent, which means Edmonton will have time to negotiate with him, and they can match any contract he signs. Last year, the Blues snagged RFAs Philip Broberg and Dylan Holloway away from the Oilers, so they likely won't let that happen again.
Bouchard was third on the Oilers in points this season, behind only McDavid and Draisaitl, with 67. He's been an elite offensive defenseman, helped by playing on the power play with those two forwards. If they want to sign him for eight years, it would be very expensive, but they could give him a bridge deal to buy out his RFA years.
AFP Analytics projects Bouchard's contract at eight years and nearly $11 million annually. That puts him in the class with Rasmus Dahlin, Erik Karlsson, and Drew Doughty. If they could get McDavid in at any price and Bouchard in at a little bit below that, they could sign that depth.
The Oilers have Corey Perry, Kasperi Kapanen, Trent Frederic, Connor Brown, and Jeff Skinner all hitting free agency this summer. Only some of those players can come back, and Elliotte Friedman recently reported that there is mutual interest between the team and Frederic. That could lead to the end of Kapanen's time in Edmonton if he can get a significant raise. The playoff experience could lead to a new deal for Skinner as well.
Anthony Beauvillier would be a strong depth addition to bring in some scoring. If they wanted to go more of a physical route, they may just keep Brown and Perry, as they are the best bottom-six options focused on the hitting side. This offseason should be about locking in two of their strongest players and adding around the edges with the hopes of winning the West again.