Heat your oven to 400 and get a large pot of water boiling for your potatoes. Add 1/4 cup flour, pinch of salt, and pepper to a small bowl and whisk together.
Toss the 2 pounds or chopped chuck roast in the flour mixture.
Heat oil in a deep, oven safe braising dish. Shake off excess flour and add in your chuck roast in batches (this avoids your meat steaming instead of caramelizing). Sear each side for about 2 minutes, remove and set onto a plate, and do another batch until all beef is seared.
Once your water is boiling, add in your potatoes until FORK tender. About 25 minutes.
Chop 5 strips of bacon and add in to your same skillet you cooked your beef in and cook until crispy. Add in about 1/4c of beef broth to scrape up bits on bottom of the dish (this is FLAVOR).
Add in chopped carrots and chopped onion and cook for 5-6 minutes. Add in 2 cloves of minced garlic, along with fresh parsley and fresh thyme. Stir well.
Add your beef back in. Add in beef broth and red wine. Add in two bay leaves and bring to a simmer for 10 minutes. Whisk up 2 tbsp melted butter and 1 tbsp flour to create a slurry. This will help thicken your stew. Add to dish along with salt and pepper to taste. Cover and put in the oven for 1 hour and 15 minutes.
Once the potatoes are done, strain out the liquid and add to a large bowl with half & half, 3 tbsp butter, lots of salt (to taste), and ground white pepper. Mash well and set aside.
Blanch the pearl onions by adding to boiling water for 2 minutes and then immediately soaking in ice water to loosen the skin, peel the first layer of skin off and set aside.
Chop mushrooms and add to a skillet with butter (2 tbsp) and splash of oil. Sear your onions and mushrooms. Add a little salt and squeeze of lemon juice at the end.
After 1 hour of beef cooking, remove from oven and add in your pearl onions & mushrooms. Cover and cook for another 25 minutes. Add a splash of beef broth if it looks dry.
Take out your beef and this is optional but I like to shred some of the pieces of beef. This is just a personal preference and ease of eating. using an ice cream scoop, add potatoes on top, brush with butter, and bake at 400 for 20 minutes. Broil at the end to brown for only a couple minutes.
Top with chives and fresh parsley. Enjoy!