The failure of U.S. policy toward Iran, Iraq, and Syria—the major Shia-led nations in the Middle East—creates significant risks for regional stability. These include a lethal conflict with Iran; upward pressure on oil prices; an Iraq caught between Iran’s orbit and state failure, and a rogue Syria fused to Russia and Iran. Neither Donald Trump nor Iran’s leaders want all-out war, but deadly skirmishes inside Iraq between U.S. and Iranian troops are likely. Iran will disrupt more tanker traffic in the Persian Gulf and hit the U.S. in cyberspace. It may also use its proxies in other Middle East countries to target U.S. citizens and allies. The chance is rising that the Iraqi government will expel U.S. troops this year, and popular resistance from some Iraqis against Iran’s influence there will strain the Iraqi state—OPEC’s second-largest oil producer. Feckless U.S. policy in Syria will also drive regional risk in 2020.