Maple Leafs’ 5 Worst Trades of the Past Decade – The Hockey Writers – Maple Leafs History

Tyson Barrie recently announced his retirement from the NHL after 14 seasons and 822 career games, many as an effective offensive defenceman and occasional power-play quarterback. With over 500 career points, he enjoyed five seasons of more than 50 points and seven seasons of double-digit goal totals. But, despite his impressive resume, his one season with the Toronto Maple Leafs wasn’t among his career highlights.

Barrie will inevitably be remembered as a key part of the underwhelming return when the organization traded Nazem Kadri to the Colorado Avalanche. The 2019 offseason deal saw Toronto ship out the sometimes temperamental and undisciplined Kadri for a dynamic blueliner in Barrie and a speedy middle-six forward in Alex Kerfoot. Unfortunately, the club lost a heart-and-soul player for an underwhelming return.

In NHL markets like the Avalanche and Edmonton Oilers, Barrie may be celebrated for his contributions. Here, however, we will use the veteran defenceman’s retirement to explore where the Kadri-for-Barrie (and Kerfoot) trade ranks among the franchise’s worst over the past decade*. These are the Maple Leafs’ five-worst trades of the past 10 years:

*Note: We are considering all trades made as of the summer of 2015 and onward.

Dishonorable Mention

Several recent bad deals didn’t make the top five. The Dion Phaneuf era ended with a whimper when the former captain was traded in February 2016 for four players and one draft pick who would play just 54 total games in Toronto. However, Phaneuf’s subsequent tenure with the Ottawa Senators and Los Angeles Kings was just as underwhelming as what Jared Cowan, Colin Greening, Milan Michalek and Tobias Linberg offered the Maple Leafs.

In another disappointing trade with the Senators that centred around a defenceman, Cody Ceci became a target of Maple Leafs fans’ ire after the 2019 deal that brought him to Toronto for Connor Brown, Nikita Zaitsev and Michael Carcone. Apart from giving up a useful forward in Brown, the Maple Leafs didn’t lose much here, apart from some fans’ hair as they watched Ceci’s numerous defensive miscues.

Finally, Toronto paid handsomely to land Ryan O’Reilly at the 2023 Trade Deadline, shipping out four draft picks and minor leaguers Mikhail Abramov and Adam Gaudette for the hometown star….