What went wrong? A look at the 5 worst trade deadline deals in Maple Leafs history

Losing on the ice can hurt for a day or two, losing in the front office can hurt for years. As we’ve seen countless times in the past, a single bad trade is enough to destroy a franchise’s future for seasons to come.
With the NHL’s trade deadline just a day away, at least a few teams are sure to make a move that will have everyone asking how the hell did that happen when we look back on it in a few years. The Toronto Maple Leafs are no stranger to such trades, and to avoid repeating the past we must understand what went wrong as we look at five of the worst trade deadline deals in Maple Leafs franchise history.
Since trades leading up to deadline day have become more and more common, we’ll take a look at any trades that happen in the week leading up to the deadline while trying to figure out what went wrong.
The Trade
On March 13th 1978, the Toronto Maple Leafs acquired Dan Maloney and a 1980 second round pick for Errol Thompson, a 1978 first round pick, a 1978 second round pick, and a 1980 first round pick. 
The Logic
Punch …

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Author: Filipe Dimas / The Leafs Nation

Ben Cherington to be named Pirates’ general manager

A significant part of the Blue Jays’ front office is set to move on. According to Jason Mackey of the Pittsburgh Post-Gazette, Ben Cherington, the senior vice president of baseball operations, has accepted the Pittsburgh Pirates’ general manager role.

According to multiple sources, Ben Cherington has accepted the Pirates GM job and is currently in Pittsburgh. Story to come.
— Jason Mackey (@JMackeyPG) November 15, 2019

Though the deal isn’t yet official, it appears as though the Pirates will be a formal announcement on Monday that Cherington will be steering the ship. (Get it? Ha haaaa!)
Cherington has been with the Blue Jays for three years now, but he’s mostly known for his work with the Boston Red Sox. He worked his way up the organization through the scouting and player development side before becoming the team’s general manager after Theo Epstein left in 2011.
He orchestrated one of the biggest salary dumps in league history, sending Carl Crawford, Adrian Gonzalez, and Josh Beckett to the Dodgers, freeing up an incredible $258 million in commitments in one deal. After a horrendous 2012 season, Cherington made a bunch of under-the-radar additions, such as Mike Napoli, Shane Victorino, and Stephen Drew, that ultimately helped the …

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Author: Cam Lewis / Blue Jays Nation