The Toronto Maple Leafs are standing at a crossroads after a season that saw them hit their lowest point in a decade. But how quickly they can bounce back may all come down to one night: Tuesday's NHL Draft Lottery.

For the first time in years, the Maple Leafs have a real shot at the No. 1 overall pick—and the chance to select generational talent Gavin McKenna. But there's a catch that has Toronto fans holding their breath. If the lottery doesn't go their way, that prized pick could slip right into the hands of their rivals, the Boston Bruins.

With new GM John Chayka now at the helm, the winds of change are blowing through Toronto. Tuesday's lottery results will set the tone for what could be a transformative offseason—for better or worse.

Here's the breakdown of the conditions that could send the Maple Leafs' first-round pick to Boston—and what it means for the future.

How the protection works

Toronto's first-round pick is only protected if it lands inside the top five. The Maple Leafs finished with the fifth-worst record in the NHL this season, giving them the fifth-highest odds in the lottery. That means they're in a delicate position: good enough to have a shot at a top pick, but vulnerable enough to lose it.

If a team behind Toronto jumps into the No. 1 or No. 2 spot, the Maple Leafs could fall outside the top five—and that would trigger the condition sending their pick straight to Boston.

What happens if the pick is top-five?

If Toronto keeps its pick this year by landing in the top five, the condition rolls over to the 2027 draft—but with even more complexity. In that scenario, the Maple Leafs would have options depending on where their 2027 pick lands:

• If the 2027 pick is inside the top 10, Toronto can choose to send it to Boston and give the Philadelphia Flyers their unprotected 2028 first-round pick.
• Alternatively, they could send the 2027 pick to Philadelphia and give Boston their unprotected 2028 first-round pick instead.

It's a high-stakes chess game that could shape the franchise for years. For a team already facing big decisions, Tuesday's lottery is just the first move in what promises to be a pivotal offseason.