1. Preheat oven to 450 degrees. Place potatoes in foil. Gently coat potatoes in 2 Tbsp cooking oil, 2 pinches of salt, and 1 pinch of pepper. Wrap potatoes securely in the foil, place on the roasting pan and roast for 20 minutes.
2. While potatoes are roasting, heat 1 Tbsp cooking oil in large skillet on medium heat. Once skillet is hot, add chicken thighs laying them flat side down and sear until nicely browned, about 6 minutes.
Turn the chicken over and cover, adjusting the skillet heat to medium/low. Simmer for 3-4 minutes, until chicken has reached an internal temperature of 165 degrees. Remove chicken from skillet and plate. Set the skillet aside.
3. In a separate bowl, combine the chimichurri ingredients and lightly toss. Pour the sauce over the chicken.
4. For the Garlic Oil, smash, peel, and mince the 1⁄2 head of garlic. Transfer to a medium pot, add the 1⁄2 cup of grapeseed oil, and heat over medium for 3 minutes. Reduce to low and continue to cook for 10 minutes. Add salt. Remove from heat.
5. Remove potatoes from oven and open carefully. Use the bottom side of a cup to lightly smash the potatoes to about half an inch in thickness.
Drizzle the garlic oil over the smashed potatoes, season with a pinch of salt and pepper, and place back in oven for 10 minutes at 400 degrees. Once done, remove from oven and plate.
6. In a separate bowl, combine the olive oil & lemon vinaigrette ingredients and stir. Set aside.
7. Using the same skillet that was used to cook the chicken, raise heat to medium. After the existing liquid begins to bubble, add broccolette and cook for 3 minutes, occasionally tossing.
Next, add the cherry tomatoes, and continue to toss every 30 seconds as to not burn your veggies. Finally, add the olive oil and lemon vinaigrette. Remove the broccolini and tomatoes from heat and transfer to serving dish.
8. Feel free to serve family style or plate individually. Enjoy!