Toronto Maple Leafs: Who Will be the First Player Traded this Season?

Toronto Maple Leafs general manager Brad Treliving, who was hired on May 31, 2023, a few days after Memorial Day, had a tidy, quiet summer.

He crossed off a few things on his to-do list: he signed some free agents on July 1; got star center Auston Matthews to agree on a long-term extension; and gave head coach Sheldon Keefe some security by lengthening his pact with the Toronto Maple Leafs by two years.

There is one rather large piece of business left for the Leafs decision maker: the looming status of free-agent to be William Nylander, the forward whose current deal runs out at the end of the upcoming campaign.

Other than those items, Treliving enjoyed a couple of pretty ho-hum, cottage lifestyle type of months. Now, it’s post-Labor Day and winter is coming. The Leafs report for training camp in less than two weeks.

Sure, this is not Treliving’s first stampede, but he’s about to experience a rodeo inside a fishbowl – something that is unique inside the hockey market: the pressure of being the cowboy to pull the Maple Leaf reins.

So far, Treliving has not veered too far off the trail. Yes, he made a few somewhat questionable signings, but he wanted to brand this team in his image: gritty and pesky.

However, Treliving has yet to make his first trade for his new team, and, although there should be lots of ups for the Leafs this year, when the valleys come, the fan base and media will clamor. When that happens, Treliving could send a player or two on a first-class flight to another city.

Who will be the first Maple Leaf traded in 2023-24? It would have to be one of the incumbent players brought in by former Leaf GM Kyle Dubas outside of the ‘Core Four’ and defenseman Morgan Rielly.

Let’s examine the top three candidates in reverse order of likelihood.