As a publisher of newspapers across Montana, I spend a lot of time thinking about free speech, what it means, what it doesn’t mean, and how it plays out in our everyday lives. That reflection recently led me to two very different public figures: Charlie Kirk and Jimmy Kimmel.

On the surface, they couldn’t be further apart in style, politics, or audience. Yet in their own ways, they have both pushed boundaries, spoken freely, and sparked strong reactions.

Kirk, a conservative commentator, built a following by challenging institutions and voicing views that many found controversial or even offensive. Kimmel, a late-night comedian, makes a living by lampooning politicians and cultural trends, often with a sharp progressive edge.

Their audiences laughed, cheered, and applauded in agreement

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