Bring a large pot of salted water to boil.
While the water comes to a boil, scrub the clams.
Heat large sauté pan over medium high and add olive oil. Once oil is shimmering, add bacon and cook until fat is rendered. Remove bacon from pan with slotted soon and set aside.
Add fennel and onion to pan and cook until onion is transparent and fennel is fragrant, about 5 minutes. You don't want the onion to brown so reduce heat slightly if necessary. Add garlic and cook for another 30 seconds until fragrant.
Add tomatoes, wine, black pepper and cayenne pepper and simmer on high for about 5 to 7 minutes until sauce begins to thicken and is slightly reduced.
Add clams to sauce and cover, shaking the pan periodically.
Check on the clams after they have been cooking for 5 minutes. Pluck out any clams that have opened and place them into a large bowl. Continuing rescuing the clams from the pot as they open. It can take up to 15 minutes or so.
While clams are cooking, cook pasta just shy of al dente.
Drain pasta and add it to pan with the sauce. Gently combine pasta with sauce to coat. Either put clams back in pot, garnish with herbs and serve as is, or put pasta on a nice serving platter and top with clams and herbs.