Two centuries ago, public armies replaced private ones as the dominant tool of warfare. Now, private armies are back ... It is a familiar story. A superpower goes to war and faces a stronger-than-expected insurgency in distant lands, yet has insufficient forces to counter it because of political and military constraints. The superpower decides to hire contractors, some of whom are armed, to support its war effort. The armed contractors prove to be both a blessing and a curse, providing vital security services to the campaign, yet at times killing innocent civilians, causing strategic setbacks, and damaging the superpower’s legitimacy. Without these contractors, the superpower could not wage the war. With them, it is more difficult to win. ... The armed contractors in question are not in Iraq or Afghanistan but in northern Italy, and the year is not 2007 but 1377. The superpower is not the United States but the papacy under Pope Gregory XI, fighting the antipapal league led by the duchy of Milan. The tragic killing of civilians by armed contractors did not occur in Baghdad but in Cesena, 630 years earlier. The military companies employed were not DynCorp International, Triple Canopy or Blackwater, but the Company of the Star, the Company of the Hat and the White Company. Known as free companies, these for-profit warriors were organised as corporations, with a well-articulated hierarchy of subcommanders and administrative machinery that oversaw the fair distribution of loot according to employees’ contracts. CEO-like captains led these medieval military corporations. ... The United Arab Emirates (UAE) has hired hundreds of Latin-American mercenaries to fight the Iranian-backed Houthis in Yemen. After years of struggling against Boko Haram, Nigeria finally employed mercenaries to do the job, and they did. Russia’s President Vladimir Putin has sent mercs to ‘liberate’ eastern Ukraine, a conflict that still simmers. Mercs are reportedly working in parts of Iraq. ... ‘durable disorder’: global governance that contains rather than solves problems. Such a world is already upon us.

The conversion of crop dusters into light attack aircraft had long been part of Prince’s vision for defeating terrorists and insurgencies in Africa and the Middle East. In Prince’s view, these single-engine fixed-wing planes, retrofitted for war zones, would revolutionize the way small wars were fought. They would also turn a substantial profit. The Thrush in Airborne’s hangar, one of two crop dusters he intended to weaponize, was Prince’s initial step in achieving what one colleague called his “obsession” with building his own private air force. ... The story of how Prince secretly plotted to transform the two aircraft for his arsenal of mercenary services is based on interviews with nearly a dozen people who have worked with Prince over the years, including current and former business partners, as well as internal documents, memos, and emails. Over a two-year period, Prince exploited front companies and cutouts, hidden corporate ownership, a meeting with Russian arms dealer Viktor Bout’s weapons supplier, and at least one civil war in an effort to manufacture and ultimately sell his customized armed counterinsurgency aircraft. If he succeeded, Prince would possess two prototypes that would lay the foundation for a low-cost, high-powered air force capable of generating healthy profits while fulfilling his dream of privatized warfare.

Uganda, in East Africa, is home to 37 million people and one of the poorest countries in the world. It’s perhaps best known for the dictator Idi Amin, who came to power in 1971 and murdered 300,000 of his countrymen during an eight-year reign. Although the country borders tumultuous South Sudan and the Democratic Republic of the Congo (DRC), Uganda today is an island of relative political stability. The economy hums. Shopping malls bloom around the capital. Its people, to generalize, are deeply religious, family-oriented, and averse to profanity. Winston Churchill dubbed Uganda the Pearl of Africa in part for its friendly people. ... It’s also one of the leading providers of mercenaries—or “private military contractors,” as the security industry prefers to call them. They are at once everywhere and nowhere. On TV, a company called Middle East Consultants runs advertisements looking for able-bodied young men to send to Dubai. Talk to taxi drivers as you bump along dirt roads in the capital, Kampala, and each has a friend or cousin or neighbor who raves about the fortune he’s made guarding some embassy or joining the war in Iraq. But official numbers and interviews with the kind of multinational companies that go to countries such as Uganda to find soldiers are hard to come by. ... A decade ago, after con men began running employment frauds on mercenary hopefuls, the Ministry of Gender, Labour, and Social Development created the External Employment Unit, an agency meant to track men leaving to serve abroad. ... Mercenary remittances surpassed coffee exports in 2009, according to the Ministry of Gender, Labour, and Social Development. Interpol’s Kampala bureau conducts roughly 1,000 background checks on Ugandans heading abroad for security jobs every month

Malhama Tactical isn’t an enormous military conglomerate like the infamous Blackwater (now named Academi). It consists of 10 well-trained fighters from Uzbekistan and the restive Muslim-majority republics of the Russian Caucasus. But size isn’t everything in military consulting, especially in the era of social media. Malhama promotes its battles across online platforms, and the relentless marketing has paid off: The outfit’s fighting prowess and training programs are renowned among jihadis in Syria and their admirers elsewhere. It helps that until now the group has specialized its services, focusing on overthrowing Bashar al-Assad’s regime and replacing it with a strict Islamic government. ... The group’s leader is a 24-year-old from Uzbekistan who goes by the name Abu Rofiq (an Arabic pseudonym that means father of Rofiq). Little is known about him other than that he cycles through personal social media accounts rapidly, using fake names and false information to throw off surveillance efforts. ... Since launching in May 2016, Malhama has grown to do brisk business in Syria, having been contracted to fight, and provide training and other battlefield consulting, alongside groups like the al Qaeda-affiliated Jabhat Fateh al-Sham (formerly known as the Nusra Front) and the Turkistan Islamic Party, a Uighur extremist group from China’s restive Xinjiang province.