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If you have time, let the chuck roast rest at room temperature for 30 minutes.
Preheat oven to 350F.
Slice the chuck roast into short rib-sized pieces, about 4" long.
Season all sides generously with salt, black pepper, and flour. Dust off any excess.
In a large braiser or dutch oven over medium high heat, add the olive oil. Heat up for 1 minute.
Add the seasoned chuck roast pieces to sear 2-3 minutes untouched on both sides, until deep golden brown. Remove from pan.
Add the chopped leeks, carrots, and celery to sauté 2-3 minutes. Stir in the red wine and brown sugar.
Place the chuck roast pieces back into the pot, submerging in the red wine and vegetables. Add the stock, garlic heads, and fresh herbs.
Cover with a lid and place on the middle oven rack to slow cook 2 ½ - 3 hours. Check on them at 2 hours to see if fork-tender, then every 20 minutes there after.
Once fork-tender, remove from the oven. Place the chuck roast on a plate and cover with foil to keep from drying out.
Remove the vegetables with a slotted spoon. Bring the pan sauce to a boil then simmer for 4-5 minutes, until reduced by half.
Enjoy the red wine-braised beef over mashed potatoes with the vegetables and a spoonful of the reduced red wine sauce. Garnish with fresh chives.