Building a roster of all-time Maple Leaf trade regrets

With a few days to go until the trade deadline, Kyle Dubas and the Maple Leafs still haven’t pulled off their big move. Or maybe they have, and Jack Campbell was it. But most of the fan base seems to be expecting something bigger, preferably a top-four defenseman. And while Dubas doesn’t have much in the way of picks to work with, he could surely work a blockbuster using guys off of the current roster, or from the prospect pipeline. Do it Kyle! Swing for the fences!

Just one thing: Do not under any circumstances trade away somebody we’re all going to regret losing.

That’s the tricky part of making trades. Fans love the short-term adrenaline rush of seeing a big deal cross the wire. But something has to go the other way, and that will often be a player or two or more. And sometimes, those players can turn out to be pretty good.

That’s where the regret comes in, along with that sense of disbelief that anyone ever thought it would be a good idea to give up that guy in the first place. It’s a feeling that Maple Leaf fans know well.

How well? How about well enough to fill out a full roster, which is what we’re going to do today. Just in case there were any Leaf fans out there with a little bit of hope and optimism still clinging to this rollercoaster of a season, let’s wring that right out with a full 20-man roster of guys that the Leafs probably wish they hadn’t traded away.

A few quick ground rules. First, we’re only worried about what the player did over the course of his career after being traded away by the Leafs. We’re looking at trades only, not guys lost to free agency or waivers or various drafts. And finally, we’re only considering players, not draft picks.

That last one is important because it removes a few names you might be expecting to see. Scott Niedermayer was never Maple Leafs’ property. Neither were Tyler Seguin or Roberto Luongo, or John Gibson or Roman Josi, or any number of good players who were drafted with picks that teams acquired from Toronto. The Leafs have certainly had a bad habit of trading high picks over the years, and it almost always works out great for the team on the other side. But trading a pick isn’t the same as trading a player, and you never know who your team might have taken if they’d stayed in that spot. While it costs us some star power, we’re going to stick to players who actually belonged to the Leafs.

The good news is that we still have plenty of candidates to choose from. And by good news, I mean let’s all hold hands and feel sad together. We’ll build this team the way all those Dubas critics insist on, from the net out …

Goaltenders

Bernie Parent

The trade: Parent bounced around a bit early in his career, going from the Bruins to the Flyers to the Leafs before flirting with the WHA. That led to the Leafs sending his rights back to Philadelphia in 1973.

What he did once he left: Parent returned to the NHL for the 1973-74 season and immediately won the Vezina, Conn Smythe and Stanley Cup. Then he did it all again the next year. He was inducted into the Hall-of-Fame in 1984.

But it’s OK because the Leafs got: The 10th overall pick in the 1973 draft, which they used on Bob Neely. He played five NHL seasons and scored 36 career goals as a Leaf.

Tuukka Rask

The trade: Heading into the 2006 offseason, Maple Leafs GM John Ferguson Jr. found himself with two can’t miss goaltending prospects, but nobody to hold down the starting job at the NHL level. He kept Justin Pogge and sent Rask to the Bruins.

What he did once he left: Rask is in his 11th season in Boston, most of those as a starter. He’s won a Vezina, is closing in on the 300-win club and was part of a Cup winner in 2011.

But it’s OK because the Leafs got: Andrew Raycroft, in a straight-up deal. He lasted one season as the starter in Toronto, leading the league in goals against and then lost his job to Vesa Toskala. That may be the most depressing sentence I’ve ever written.

But remember, the Leafs also got to keep Pogge, who played (checks notes) seven NHL games. A lot of people forget that part.

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