Add olive oil to a large, heavy skillet on medium heat. Season the short ribs with salt & pepper.
Once the oil is hot, add the short ribs. You'll likely need to do two batches. Don't crowd the pan. Sear for 3-4 minutes per side.
Add all the other ingredients to the Crockpot except for the cornstarch. Give it a stir. Add the short ribs in as even of a layer as possible (some will likely stick out and that's ok). Cook on high for 5-6 hours or low for 7-8 hours.
Once the ribs are done, skim the fat off the surface (I just use a small spoon to do this). Mix the cornstarch with about a tablespoon of cold water until you've got a smooth mixture, then stir it into the Crockpot. Let it sit for about 5 minutes to thicken the sauce up a bit. Add extra salt & pepper if desired. Serve with mashed potatoes or other side dishes.
Cook for 5-6 hours on high or 7-8 on low. I always suggest adding salt "to taste" because everyone's salt preference is subjective, but I did add more salt to this than I normally would to a dish, partially because there's a whole bottle of wine in there, and it does serve 6+ people. This dish freezes well.