They have a lot in common. Both men run autocratic, secretive, oil-based, global operations. And they like each other enough that they’ve joined forces in perhaps the biggest joint venture in the global oil industry. At a time when Putin has shown nothing but contempt for all other high-level American leaders, here’s hoping that the Tillerson-Putin “bromance” (and the threat of having it broken up by Washington sanctions) can help keep the Russian President from doubling down on crazy.

Exxon’s landmark 2011 joint venture with Kremlin-controlled Rosneft calls for upwards of $500 billion in investment over the coming decades. The companies are planning an offshore drilling campaign in Russia’s frozen Chukchi Sea, Laptev Sea and Kara Sea, as well as the Black Sea. They’ll also be drilling onshore in western Siberia, where the Bazhenov and Achimov formations are thought to be many times bigger than the Bakken shale of North Dakota. In addition, Exxon and Rosneft are working to finalize designs for an LNG project in Russia’s far east.

As in any good bromance, they hang out in each others’ neighborhoods. To balance out the geographic breadth of the partnership, Rosneft has joined with Exxon to invest in 20 deepwater exploration blocks in the Gulf of Mexico, as well as onshore projects in Texas and Alberta, Canada. Exxon has also given Rosneft the option to acquire a 25% stake in the Port Thomson Unit, which is estimated to hold a quarter of the natural gas and condensate reserves on Alaska’s North Slope.