Add pork to pan; cook 7 minutes, turning to brown on all sides.
Remove pork from pan; keep warm.
Add remaining 1 teaspoon olive oil to pan; swirl to coat.
Add onion to pan; cook 5 minutes or until onion begins to brown, stirring occasionally.
Add chicken broth and next 4 ingredients (through garlic) to pan; bring to a boil, scraping pan to loosen browned bits. Return pork to pan. Cover and bake at 325 for 1 1/2 hours.
Add kale to pan; cover and bake at 325 for 30 minutes.
Heat a large nonstick skillet over medium-high heat.
Add canola oil; swirl to coat.
Add apples; cook 3 minutes or until starting to soften.
Add vinegar and brown sugar; cook 1 minute or until sugar dissolves and liquid almost evaporates.