Name: Charred Pineapple Jalapeño Chili (Cookoff Edition)
Prep time: 50 min
Cook time: 1 h
Total time: 1 h 50 min
Yield: About 13
Ingredients: 2 lb ground turkey (85/15); 1 red bell pepper, diced; 1 green bell pepper, diced; 1 yellow bell pepper, diced; 2 yellow onions, diced; 4 garlic cloves, minced; 4 fresh jalapeños, charred and diced; 6 fresh pineapple rings, charred and diced; 4 fresh pineapple rings, diced (for finishing); 1 can (15 oz) Del Monte Golden Sweet whole kernel corn, drained; 2 cans (14.5 oz each) Del Monte Zesty Chili Style diced tomatoes; 1 can (16 oz) Bush's Maple Cured baked beans; 2 cups water (stovetop only; add more if needed); 2 limes, halved (charred if you like); Oil, for cooking; 3 tbsp (about 1½ oz) tomato paste; 2–3 dried ancho chiles, made into a paste (see below); 4 tsp chipotle chili powder; 1 tsp smoked paprika; 2 tsp cumin; 1 tsp Mexican oregano; 1 tbsp onion powder; 1 tbsp garlic powder; 1 tbsp cayenne (reduce for milder); 2 tsp black pepper; 1 tsp salt, plus more to taste; 1/4 cup brown sugar; 1 tbsp Worcestershire sauce; 1–2 tsp beef bouillon paste; 1/4 cup Cholula

How It Comes Together

Jalapeños blistering over the open flame of a gas stove

Char the pineapple and jalapeños.
A searing-hot skillet, a kitchen torch, the open flame of a gas stove, or the broiler on high with the tray closest to the heat all work. You want dark, blistered spots on the skin, not burnt through. Wear gloves for the jalapeños — most of the heat is in the seeds and white ribs, so leave a few in if you want more kick.
Soften the vegetables.
In a big pot with a little oil and a pinch of salt, cook the onions over medium-low until soft and see-through, about 8–10 minutes. Add the garlic for a minute, then the bell peppers until they soften, then the corn.
Brown the turkey hard.
Meanwhile, in a skillet over medium-high to high heat, break the turkey up once and mostly leave it alone. It'll release a lot of water at first; let that cook off until it sizzles and gets crusty brown bits, with about half the crumbles well browned and a brown layer on the bottom of the pan. That browning is where the flavor comes from.

The chili simmering uncovered in a big pot as the broth cooks down

Build the flavor base.
Turn the skillet down to medium. Push the turkey aside, add the tomato paste and homemade ancho paste mixed together, and cook 1–2 minutes until it darkens and starts to stick. Stir it through the meat, sprinkle in the dry spices and brown sugar and stir for about a minute until fragrant, then add the Worcestershire and bouillon.
Bring it together and simmer.
Add the turkey to the pot with the tomatoes, beans, charred jalapeños, charred pineapple and Cholula. Pour a splash of the water into the hot skillet, scrape up every stuck bit, and add that to the pot with the rest of the water. Simmer uncovered, stirring now and then, until the broth cooks down.
Finish fresh.
Stir in the fresh pineapple and a squeeze of lime. Taste and adjust salt. This is the step that makes it come alive.

Make It a Day or Two Ahead

I make this two days before I serve it, and the flavors deepen in the fridge. Cool it quickly in shallow containers or mason jars (leave an inch at the top) and refrigerate within 2 hours. It keeps 3–4 days. Reheat until steaming hot, then add the fresh pineapple, lime and toppings. Hold back the fresh pineapple and lime until then so they stay bright.

What I Learned Making It

Brown the turkey on high heat. On lower heat it just steams in its own water and turns gray.
Scrape the skillet with some of your water. All those stuck brown bits are flavor.
Use less water than you think. Three cups made it too brothy and it took a long time to cook down; I'm going with 2 cups and adding more only if needed.
It looks brothier while it's bubbling. Turn off the heat and let it settle for a minute before deciding it's done. It's ready when the solids show through and the broth lightly coats a spoon.
The stovetop tastes better than the slow cooker. On the stove everything browns and the broth reduces, so the flavor is more concentrated.
Don't judge it before the finishers go in. Tasted on its own, the deep ancho and chipotle flavors can seem heavy. Once I stirred in the fresh pineapple and lime, it tasted great.
Small batches of ancho paste are hard to blend in a big blender. An immersion blender in a tall, narrow cup works best.
Wear gloves for the jalapeños. If your hands burn, rub in a little cooking oil for a minute, then wash with dish soap; soaking in cold milk helps too.

Questions

Can I make it in a slow cooker?: Yes. Brown the turkey and build the flavor base the same way, then add everything except the water, fresh pineapple and lime to the slow cooker. Cook on LOW for about 8 hours, taking the lid off and switching to HIGH for the last 1–2 hours so it cooks down. A slow cooker traps moisture, so you won't need the water.
Where do I find dried ancho chiles?: Usually in the Hispanic or international aisle, in bags of whole dried chiles.
Is it very spicy?: It has a solid kick from the chipotle, jalapeños and cayenne, but the heat fades after about a minute. Cut back the cayenne to make it milder.
Can I use canned pineapple?: Fresh is better for charring, because canned is soaked in syrup and steams instead of caramelizing.
Should I char the lime?: It's optional. Charring makes the juice a little sweeter and smokier: torch the cut side until blistered, or press it cut-side down in a hot skillet for a couple of minutes. A regular squeeze of fresh lime works great too.
What should I top it with?: Diced avocado tossed with a little lime juice so it doesn't brown, and cilantro on the side for anyone who likes it. A lime wedge on top looks great. I serve it in a white bowl so the colors pop.

Want the original? Try my Amazing Jalapeño Pineapple Slow Cooker Chili.