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Spread fennel and onion in an even layer in a 5- to 6-quart slow cooker. Cover and refrigerate fennel fronds.
Sprinkle pork with 3/4 teaspoon each salt and pepper. Heat 1 tablespoon oil in a large skillet or Dutch oven over medium-high heat. Add about half the pork and cook until brown, 4 to 5 minutes. Transfer to the slow cooker. Repeat with the remaining oil and pork. Add wine to the pan and scrape up any browned bits; remove from the heat.
Sprinkle garlic, rosemary, oregano and the remaining 3/4 teaspoon each salt and pepper over the pork. Top with the drained tomatoes and pour in the wine from the skillet.
Cover and cook for 5 hours on High or 7 to 8 hours on Low. Stir the stew well to combine; serve garnished with the reserved fronds.