In a small saucepan over medium heat, melt the butter. Continue cooking, stirring often to prevent the milk solids from burning, until the butter foams and then darkens in color slightly and is very fragrant, 4 to 6 minutes. Immediately pour the butter into a large heatproof bowl. Do not wash the pan.
To the saucepan used to melt the butter, add the red wine and 2 tablespoons (32 grams) of the granulated sugar and bring to a simmer over high heat. (Be careful; the wine will sizzle when you pour it in the pan.) Reduce the heat to medium and simmer, stirring occasionally, until reduced to ⅓ cup (79 ml), 16 to 18 minutes. (The easiest way to test if the reduction is ready is to pour it into a heatproof measuring glass to see if it’s at the ⅓-cup mark.) Pour the reduced wine into the bowl with the butter and let the mixture cool for 15 minutes.
As the butter/wine mixture cools, whisk together the flour, cocoa powder, baking powder, baking soda, and salt in a medium bowl. Preheat the oven to 350°F and set 2 racks at the upper-middle and lower-middle positions. Line 3 baking sheets (or as many as you have) with parchment paper or nonstick baking mats.
Whisk both the brown sugar and the remaining ⅓ cup (67 grams) granulated sugar into the butter/ wine mixture, then whisk in the eggs and vanilla extract until smooth. Add the flour mixture and stir with a rubber spatula until a soft dough forms, then stir in the chopped chocolate.
Using a large 2⅓-inch (#16) cookie scoop or ¼-cup measure, portion out the dough and roll into large balls. Place the dough balls at least 3 inches apart on the prepared baking sheets (6 per sheet).
Bake 2 sheets at the same time, swapping the top sheet to the bottom rack and bottom sheet to the top midway through baking, until the tops lose their shine but their cracks still appear slightly wet (don’t be tempted to overbake), 11 to 14 minutes, then bake the remaining baking sheet of cookies on either rack. Let the cookies cool completely on the baking sheets.
If wrapped tightly in plastic, the finished dough can be stored in the refrigerator for several days before baking. If too firm to scoop, let sit at room temperature for 15 minutes and try again.
