At the heart of the high-stakes U.S. program to train and equip Syrian rebels to fight ISIS is a multimillion-dollar arms deal that the Pentagon farmed out to a tiny, little-known private company called Purple Shovel LLC. A BuzzFeed News investigation, based on inside documents and confidential sources familiar with the Syria operation, has found:

▸ Purple Shovel, through the subcontractors it selected and oversaw, tried to sell the U.S. thousands of Russian-style rocket-propelled grenades that were considered unreliable because they were manufactured three decades ago, before Mikhail Gorbachev came to power in the Soviet Union.

▸ The U.S. government rejected them, and that delayed to the effort to stand up the Syrian rebel force.

▸ An American contractor, 41-year-old Francis Norwillo, was killed in a weapons explosion in Bulgaria while training with such outdated grenades.