Toronto Maple Leafs: The Smallest Trades Hurt the Most

RALEIGH, NC - JANUARY 30: Tim Gleason
RALEIGH, NC - JANUARY 30: Tim Gleason /
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This may come as a shock to many of you, but the Toronto Maple Leafs have made some pretty awful trades throughout their century of existence.

We all know the greatest hits, right?

Tom Kurvers to the Devils for what became Scott Niedermayer is physically painful to remember. Recalling how Brian Burke handed Anaheim the picks they used to draft John Gibson and Rickard Rackell just so he could move up eight spots and select Tyler Biggs is enough to bring on an ulcer.

And Tuukka Rask for Andrew Raycroft may go down as the worst trade in NHL history.

Those are all comically bad trades, ones symbolizing a general manager stepping up to the plate, swinging away, and whiffing so hard that it shatters every bone in his body. Basically, if Pablo Sandoval was an NHL GM, each of the aforementioned trades are his belt.

Although, while the big misses can set a team back for decades (just look at Edmonton), the smaller, less obvious whiffs are just as painful, albeit in a different way.

Which brings me to Tim Gleason.

John-Michael Liles for Tim Gleason

The year is 2018, and the Toronto Maple Leafs are still paying Gleason, who has been happily retired since 2015.

Dave Nonis strikes again.

On New Year’s Day, 2014, the Leafs and Carolina Hurricanes swapped defenceman, as John-Michael Liles headed to Raleigh, with Gleason coming back the other way.

At the time, the deal was fairly low-profile.

Liles had essentially pioneered the now-customary Josh Leivo role on the Leafs, suiting up for just 6 games prior to the trade.

And, on the off chance he did slot into the lineup, Liles logged just above 17 minutes per game, the second-lowest average ice time of his career.

Gleason, on the other hand, was a slow, stay-at-home defenseman at a time when the NHL was rapidly transitioning towards a fast and offensively inclined mindset.

Despite players of his ilk losing relevance by the day, Nonis seemed inclined to trade for Gleason and his $4 million cap hit. A cap hit which carried on for another two years.

Good one, Dave.

In 39 games with the Leafs, Gleason finished with 5 points, a CF/60 rating of 39.2% at 5v5, and less average TOI than Liles.

And, in addition to such staggering production, Gleason’s buyout necessitated that $1.333 of his salary would count against Toronto’s cap for the next four years.

To summarize, to prevent Liles from being strapped to the press box for the remainder of the season, the Leafs went out and traded him for a worse asset whose buyout would eventually cost them more cap space than Auston Matthews‘ ELC.

Trades like these are what separates the good teams from the bad. If you can’t manage your assets properly at the micro level, you’ll likely mismanage them at the macro level as well.

So, while Liles for Gleason may not have been as big of a swing and miss as Rask for Raycroft was, it was a miss nonetheless. A miss which still impacts the Leafs cap situation four years since Gleason last donned a blue and white sweater.

Next: Enemy's Insight - Deadline Countdown

Remember, folks: small trades can be just as painful as the big ones.