Toronto Maple Leafs

Toronto Sun reporter Steve Simmons has built a reputation for asking questions that sometimes rub people the wrong way — especially when it comes to the Toronto Maple Leafs.

But Simmons’ recent exchange with Leafs goaltender Joseph Woll may have left more people scratching their heads than upset.

During media availability, Simmons asked Woll if he thought a Stanley Cup Final matchup against the Dallas Stars was “possible.” Woll, seemingly caught off guard, took the question at face value.

“Uh… yeah, isn’t it possible?” the 26-year-old goalie responded, clearly confused. Simmons then clarified that he was asking Woll for his thoughts on the potential matchup.

“Oh, I see. I was like, ‘yeah, it’s possible,’” Woll said with a smile, catching on. “Yeah, it’d be pretty cool.”

But that wasn’t the reporter’s only awkward moment of the day.

Speaking to Leafs captain Auston Matthews, Simmons broached the topic of NHL player salaries and how they stack up to other sports.

“Are hockey players underpaid for what they bring to the table?” Simmons asked.

Matthews, wary of the loaded question, avoided offering any bold take.

“Steve… I don’t know. I mean, I’m grateful to play in the NHL,” Matthews replied calmly. “That stuff, I think it gets talked about, but at the same time, I feel very blessed.”

While these exchanges were more playful than provocative, Simmons has had his share of heated moments with the Leafs in the past. In 2022, he faced backlash for a controversial op-ed about Akim Aliu, comparing him to former Leafs forward Wayne Simmonds, which led to a public defence from then-captain John Tavares.

Then, this past April, fans voiced their displeasure with the writer after he published a story on Mitch Marner’s playoff performance titled “The Invisible Leaf: When Buds need him most, Mitch Marner pulling his usual playoff disappearing act.”

The print version of the article included a photo of Marner in team gear with his face erased, making him appear invisible.