Grilled Flank Steak with Parsley-Mint Chimichurri, Roasted Fennel and Summer Squash, and Garlic Roasted Potatoes

a bold, herb-forward steak dish that lets Judy's flank get real char while the chimichurri brings sharp, bright heat she'll love

⏱ 50 min · medium · 🍽 serves 4

Ingredients

• 1 1/2 lb flank steak
• 1 1/2 lb potatoes, cut into 1-inch chunks
• 6 garlic cloves (3 minced, 3 whole for potatoes)
• 2 fennel bulbs, trimmed and cut into wedges
• 2 medium zucchini, sliced on the diagonal
• 2 yellow summer squash, sliced on the diagonal
• 1 cup packed flat-leaf parsley, finely chopped
• 1/2 cup packed mint leaves, finely chopped
• 1/2 cup extra-virgin olive oil, divided
• 3 tbsp apple cider vinegar
• 1 lemon, juiced and zested
• 1/2 tsp red chili flakes (for Judy's heat)
• Sea salt, to taste
• Black pepper, to taste

Steps

1. Take the flank steak out of the fridge 30 minutes before cooking so it comes to room temperature.
2. Heat oven to 425°F. Toss the potato chunks with 2 tbsp olive oil, the 3 whole garlic cloves, salt, and pepper on a sheet pan. Roast 35–40 minutes, shaking the pan halfway, until deeply golden and crisp.
3. On a second sheet pan, toss the fennel wedges, zucchini, and summer squash with 2 tbsp olive oil, salt, and pepper. Roast alongside the potatoes for the last 20–25 minutes, until the fennel is tender and edges are caramelized.
4. While things roast, make the chimichurri: combine the minced garlic, chopped parsley, mint, remaining olive oil, vinegar, lemon juice and zest, and chili flakes in a bowl. Season with salt and pepper, stir well, and let it sit at room temperature so the flavors open up.
5. Pat the flank steak dry and season both sides generously with salt and pepper.
6. Get a grill or heavy skillet ripping hot. Sear the steak 4–5 minutes per side for medium-rare, or push it a minute longer per side since Judy likes it charred and bold.
7. Rest the steak on a cutting board for 10 minutes, then slice thin against the grain.
8. Fan the steak slices on a platter, spoon chimichurri generously over the top, and serve with the roasted potatoes and roasted fennel and squash alongside.