The Toronto Maple Leafs Need to Make a Trade With the Oilers

The idiom, “strike while the iron’s hot” may be good advice for the Toronto Maple Leafs who have the chance to take advantage of the Edmonton Oilers.

The Toronto Maple Leafs, like the rest of the NHL world saw the news break on Monday that the Edmonton Oilers traded for Duncan Keith. Kyle Dubas should use the information he learned from that deal to make a swap of his own with the GM of the Oilers, Ken Holland.

Holland is a very well respected executive who won three Stanley Cups while with the Detroit Red Wings front office. However, he made a head scratching move trading for defenseman Duncan Keith.

It’s very difficult to explain why Holland decided to acquire a player who turns 38 on Friday and is clearly on the decline. Keith hasn’t been a dominant blue liner for a very long time. However, the money he is being paid suggests he should be better than his is. Keith has two years remaining on the massive 13-year deal he signed for $72M in December of 2009. The Oilers didn’t just trade for the player but also for his $5,538,462 AAV.

Toronto Maple Leafs Should Fleece the Oilers

Since Keith’s contract takes a considerable amount of cap space, it was expected that the Chicago Blackhawks would need to sweeten the pot if they were going to be able to unload the blue liner. That’s not at all what happened. Instead, Holland got Keith and low end prospect Tim Soderlund from the Blackhawks in exchange for a 24 year old defenseman, Caleb Jones, and a conditional third-round 2022 draft pick. The Oilers gave up assets to do the Blackhawks a favour in helping them clear cap space.

What makes this deal look worse for the Oilers is that Chicago was exploring potential trades in order to help get Keith closer to his family. If Keith, who has a no-movement clause in his contract, was limiting locations to the Pacific Northwest or Western Canada, it really only provided Stan Bowman with a list of about four possible destinations. Those were the expansion team Seattle Kraken, Vancouver Canucks, Calgary Flames, and the Oilers. This makes putting a deal together more difficult and should have only helped Holland get a better return.

The trade would be a steal if the Oilers were trading for Keith in 2010 when he won his first Norris Trophy. If somehow Holland is stuck in that decade, the Toronto Maple Leafs could get a great return for Jason Spezza. Better yet, they could re-sign Joe Thornton and send him to Edmonton for a top tier package.

In all seriousness, it’s difficult to fleece any NHL general manager. If Holland is going to take big risks in an attempt to bolster his roster for next season, Dubas needs to pick up the phone and see what he can extract from the Oilers. If a potential deal makes sense for Toronto, Dubas should play hardball in negotiations.

Due to the scrutiny Holland has already received for the Keith trade, he will be under pressure to ensure that his newest defenseman can perform at a high level. That likely means more roster moves in Edmonton. Ideally, the Toronto Maple Leafs can take advantage and see if Holland has any more lapses in judgement.

It would be great to see Keith surprise the NHL with outstanding play and silence his critics. It would be great vindication for the GM and I would eat my words. Whether or not that happens in the coming season, Dubas should still be all over Holland now.