Heat 2 tablespoons olive oil in a large pot over medium heat. Heat another 2 tablespoons oil in a skillet over medium heat.
Toss the pork loin with the flour in a bowl to coat the pork evenly.
Cook and stir the pork in the hot oil in the large pot until browned on all sides, 5 to 7 minutes. Meanwhile, cook and stir the onions in the hot oil in the skillet until soft and brown, about 10 minutes.
Pour the chicken stock into the large pot with the pork loin; add the browned onions, butternut squash, garlic cloves, minced garlic, baby carrots, celery, black olives, and crimini mushrooms. Bring the chicken stock mixture to a boil and reduce heat to medium low. Stir the Cabernet Sauvignon wine, sage, oregano, thyme, rosemary, and basil into the mixture. Place a cover on the pot and allow the mixture to simmer until fragrant and the pork loin is very tender, 2 to 3 hours.
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