Heat 1 teaspoon oil in a large Dutch oven coated with cooking spray over medium-high heat. Sprinkle beef with salt. Place half of beef in pan; sauté 8 minutes or until browned. Remove from pan. Repeat procedure with remaining beef; remove from pan.
Add 2 teaspoons oil, onion, and bell pepper to pan, and sauté for 3 minutes. Add garlic and jalapeño; sauté for 1 minute. Add wine, scraping pan to loosen browned bits. Return beef to pan.
Stir in remaining ingredients; bring to a boil. Cover, reduce heat, and simmer 1 1/2 hours or until beef is tender, stirring occasionally.
Wine note: Hearty, spicy dishes like this chili need a wine that's gutsy enough to stand up not just to the chili pepper, chile powder, cumin, and other spices, but also to the beans and beef. My top pick: a juicy Australian shiraz. Its mouth-filling, plush, almost syrupy softness is a great contrast to the beef and beans, and the wine's rich fruitiness cushions all that spice. There are loads of terrific Australian shirazes on the market at all price levels. The affordable Yalumba Shiraz 2003 (South Australia, $10) is priced right for chili. -Karen MacNeil