Top 10 Worst Trades in Toronto Maple Leafs History

The history of the Toronto Maple Leafs has had many of ups and downs, especially via trades.

Since the Toronto Maple Leafs franchise has been around for over 100 years, they’re bound to make a few dumb moves. Although the best-of list was much more fun to talk about it, these terrible trades make being a fan so special.

If you’re like me, when your favourite team makes a trade, I immediately agree with the decision. I’m not in the war-room, scouting, or playing the sport at a professional level, so who am I to judge the decision so quickly? I give the benefit of the doubt to the General Manager who made that move, assuming that the trade will work out in my teams favor.

When your favourite team is the Toronto Maple Leafs, that’s a tough pill to swallow. For years, the team has made some very bad decisions. Whether it’s through coaching, management, scouting, free agency, drafting or trading, there were some bleak years in Leafs-Land.

However, even when each transaction happened, I tried to stay optimistic. But after revisiting this list, it’s tough to understand why I felt that way.

Fortunately for the newest regime, most of the decisions they’ve made have paid off. There are still a few that I shake my head at, but the majority have been good. You’re not going to go 100 percent on your trades, but if you can hit between 80-90 percent, you’re going to have an incredibly successful career.

Speaking of which, let’s take a look at the history of the Toronto Maple Leafs and break down the top 10 worst trades in team history.