Beef Chili with Red Wine and Black Olives

Name: Beef Chili with Red Wine and Black Olives
Prep time: 15 min
Cook time: 24 min
Total time: 39 min
Yield: 6 servings
Cuisine: American
Ingredients: 2 lb (900 g) Ground beef, 85/15 blend; 2 tbsp (30 ml) Olive oil; 1 whole (250 g) Onion, large yellow, diced into ½-inch pieces; 4 cloves (15 g) Garlic, cloves, minced; 2 tbsp (30 g) Tomato paste; 1½ cup (360 ml) Red wine, medium-bodied, dry; 1 can (28 oz) (800 g) Crushed tomatoes, canned; 2 cans (15 oz each) (850 g) Kidney beans, canned, drained and rinsed; 1 cup (150 g) Black olives, pitted, halved; 2 cup (480 ml) Beef broth, low-sodium; 2 tsp (4 g) Ground cumin; 1 tsp (3 g) Smoked paprika; 1 tsp (2 g) Dried oregano; 1 tsp (3 g) Chili powder; Salt; Black pepper, freshly ground; 2 tbsp (8 g) Cilantro, fresh, chopped (optional)

From the MyKitchenBank Kitchen

A hearty, sophisticated beef chili infused with Mediterranean flavors. Red wine adds depth and richness, while black olives and dried oregano give it a distinctive character far from typical Southwestern chili. This is warming, complex, and deeply savory—not fiery, but genuinely satisfying. It improves noticeably when made ahead, so don't hesitate to prepare it a day or two in advance.

Prep: 15 min
Cook: 24 min
Wait: 40 min
Total: 1 hr 19 min
Makes: 4 to 6 servings

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Steps

Before you start

Drain and rinse canned kidney beans thoroughly
Pit black olives if needed (or use pre-pitted)
Dice the onion and mince the garlic; measure all spices
Use a medium-bodied red wine you'd be happy to drink—avoid 'cooking wine' which contains added salt

1
Sauté the aromatics
- Heat the olive oil in a large 5–6 quart Dutch oven or heavy-bottomed pot over medium heat.
- Add the diced onion and cook for about 5 minutes, stirring occasionally, until softened and translucent.
- This gentle cooking releases the onion's natural sugars and builds the foundation of flavor.
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Ready when: Onion is soft and translucent
Tip: Watch the heat carefully. If the onion starts to brown, lower the heat slightly and add a splash of water to keep it pale and sweet.
2
Add garlic and tomato paste
- Add the minced garlic and stir constantly for about 30 seconds until fragrant.
- Then add the tomato paste and stir for another 1–2 minutes, coating it in the hot oil.
- You'll notice the paste darkens, becomes more concentrated in aroma, and clings to the bottom of the pot.
- This deep toasting step is crucial for building chili depth.
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Ready when: Tomato paste darkens and becomes very fragrant
Tip: Don't skip the toasting step—it concentrates the tomato's umami and prevents the raw, tinny flavor that undercooked paste can bring.
3
Brown the ground beef
- Increase the heat to medium-high and add the ground beef in chunks.
- Break it apart with a wooden spoon as it cooks, stirring frequently to ensure it browns evenly on all sides.
- This should take 8–10 minutes.
- Don't rush this step; you want deep, dark browning, not just a gray-brown color.
- Cook longer than feels necessary if needed.
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Ready when: Beef is deeply browned throughout with no pink visible
Tip: If your pot seems crowded, brown the beef in two batches. Crowding steams the meat instead of browning it, losing flavor. A hot, uncrowded surface is your friend.
4
Deglaze with red wine
- Pour the red wine into the pot, scraping the bottom with your spoon to dissolve and lift all the browned bits (fond) stuck to the surface.
- These brown bits are pure concentrated flavor—don't leave them behind.
- Let the wine simmer for about 2–3 minutes so some of the alcohol cooks off.
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Ready when: Wine has bubbled gently and noticeably reduced
Tip: Use a wine you'd be happy to drink. Cheap 'cooking wine' often contains salt and will throw off the seasoning balance.
5
Add spices and tomato mixture
- Stir in the ground cumin, smoked paprika, dried oregano, and chili powder, stirring for about 30 seconds so the spices bloom in the hot fat and release their essential oils.
- Then add the crushed tomatoes (with their juice) and beef broth, stirring well to combine everything.
- The pot should bubble gently at this point.
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Ready when: Everything is evenly combined and bubbling gently
Tip: Blooming spices in hot fat is essential—it wakes them up and prevents that dusty, raw spice flavor. Don't add them to cold liquid.
6
Simmer and develop flavor
- Reduce the heat to medium-low and simmer the chili uncovered for 30–35 minutes, stirring occasionally (roughly every 10 minutes to prevent sticking).
- The mixture should bubble very gently; if it's boiling too vigorously, lower the heat further.
- As it simmers, the sauce will thicken slightly and the flavors will deepen, meld, and become more complex.
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Ready when: Sauce has thickened and flavors have melded into a rich, complex base
Tip: Patience here pays dividends. Chili genuinely improves when made a day or two ahead—the flavors continue developing even after cooling. Make it early if you can.
7
Add beans and olives
- Stir in the drained kidney beans and halved black olives.
- Simmer for another 5 minutes, allowing them to warm through and the flavors to incorporate.
- Don't add the beans earlier; this brief cooking time at the end preserves their texture and prevents them from breaking down into mush.
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Ready when: Beans are heated through and olives are warm
Tip: Late-stage bean addition is the secret to chunks of tender beans instead of mushy paste. The long simmer is already done; beans just need warmth.
8
Season and serve
- Taste the chili and add salt and black pepper to taste, starting conservatively (it's easy to add more but impossible to remove).
- Ladle the chili into bowls and garnish generously with fresh chopped cilantro if desired.
- Serve hot, and consider toppings like sour cream, grated cheese, or crackers on the side.
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Tip: Add cilantro fresh just before serving to preserve its bright, herbaceous flavor. Cooking it into the chili dulls it significantly.

Good to know

Tips

Brown the beef thoroughly in a hot pot without crowding. Good browning (the Maillard reaction) creates flavor that can't be replicated by just cooking gray meat. This is the foundation of great chili.
Blooming spices in fat—as done in Step 5—releases their essential oils and prevents raw, dusty spice flavor. This single step elevates homemade chili above the ordinary.
The flavor arc of this chili improves significantly over 1–2 days as the spices, wine, and tomatoes continue to marry. Plan ahead when possible, or accept that the first serving is good but tomorrow's will be noticeably better.
Stir in fresh cilantro only at the last moment before eating. Its brightness fades quickly when cooked; adding it during the long simmer wastes its potential.

Make ahead

Yes. This chili is genuinely better made 1–2 days ahead—flavors deepen and meld with time. Prepare through Step 7, cool to room temperature, then refrigerate in an airtight container for up to 4 days. To reheat, warm on the stovetop over medium heat, stirring occasionally, until heated through. Add a splash of beef broth or water if the chili has thickened too much.

Storage & reheating

Refrigerate in an airtight container for up to 4 days. Freeze in a freezer-safe container (leaving ½ inch headspace for expansion) for up to 3 months. To reheat frozen chili: thaw overnight in the refrigerator, then warm on the stovetop over medium heat, stirring occasionally, until warmed through. Add a splash of beef broth or water if needed. Chili can also be reheated gently in a covered pot in a 325°F (163°C) oven for about 25–30 minutes.

Substitutions

Ground beef, 85/15 blend → Ground lamb. Use the same weight. Lamb imparts a more distinctly Mediterranean character with earthier, slightly gamey notes that pair beautifully with the wine and olives.
Red wine → 1 cup beef broth + 1 tablespoon balsamic vinegar. Use this combination in place of the 1.5 cups red wine if you prefer a non-alcoholic version. The balsamic adds acidity and slight sweetness that replaces the wine's depth.
Kidney beans, canned → Black beans, pinto beans, or chickpeas. Each brings slightly different earthiness and texture. Black beans are earthier; chickpeas add a nuttier note. Use the same volume.
Black olives, pitted → Green olives or sun-dried tomatoes. Green olives bring more tartness and brightness; sun-dried tomatoes add concentrated tomato sweetness and chewiness. Use the same volume.