In the Syrian civil war, Iranian and Russian forces have fought side by side to keep Bashar al-Assad in power. But cooperation between Moscow and Tehran goes back much further, explains Oved Lobel:

[T]he Islamist regime has maintained a deep warmth for Russia, especially after 1988. The Soviet leader Mikhail Gorbachev was the only foreign leader ever to receive a personal letter from Ayatollah Ruhollah Khomeini (in 1989) urging him to consider Islam an alternative given the imminent collapse of Communism. . . . While the current relationship is a strategic alliance, the Soviet-Khomeini relationship was more akin to the Russo-Turkish alliance of today, in which their highest mutual priority—the destruction of U.S. influence—allowed them to compartmentalize irreconcilable ideological and geopolitical differences.

The most extreme example of this is Afghanistan, where Khomeini and Moscow came to an arrangement whereby Tehran could replicate its Islamic theocracy in Hazarajat, the area predominantly populated by the Hazara Shiite minority, while the Soviets shored up their Communist state in the rest of Afghanistan. . . . Following the sudden rise of the Taliban, Russia and Iran allied against them and backed the Northern Alliance. . . . But, following the U.S.-led invasion in 2001, the two countries collaborated in supporting the Taliban.

Since Vladimir Putin took the helm at the Kremlin, the relationship between the two has only grown stronger:

The clearest demonstration of the Russo-Iranian alliance was their joint intervention in Syria to preserve Bashar al-Assad’s regime, but their anti-U.S. alliance spans the globe. For instance, when the Palestine Liberation Organization (PLO) sought Iranian support during the second intifada, it went to Moscow to connect with the Islamic Revolutionary Guard Corp, resulting in the 2002 Karine A affair, when the Palestinian Authority tried to smuggle 50 tons of Iranian-supplied weapons into Gaza in flagrant violation of the Oslo Accords.

Last week, the New York Times reported, based on unnamed sources within the Trump administration, that the president had asked Israel not to carry out a planned strike on Iranian nuclear facilities. That is, somebody deliberately gave this information to the press, which later tried to confirm it by speaking with other officials. Amit Segal writes that, “according to figures in Israel’s security establishment,” this is “the most serious leak in Israel’s history.” He explains:

As Israel is reportedly planning what may well be one of its most consequential military operations ever, the New York Times lays out for the Iranians what Israel will target, when it will carry out the operation, and how. That’s not just any other leak.

Seth Mandel looks into the leaker’s logic:

The primary purpose of the [Times] article is not as a record of internal deliberations but as an instrument of policy itself. Namely, to obstruct future U.S. and Israeli foreign policy by divulging enough details of Israel’s plans in order to protect Iran’s nuclear sites. The idea is to force Israeli planners back to the drawing board, thus delaying a possible future strike on Iran until Iranian air defenses have been rebuilt.

The leak is the point. It’s a tactical play, more or less, to help Iran torpedo American action.

The leaker, Mandel explains—and the Times itself implies—is likely aligned with the faction in the administration that wants to see the U.S. retreat from the world stage and from its alliance with Israel, a faction that includes Vice-President J.D. Vance, Director of National Intelligence Tulsi Gabbard, and the president’s own chief of staff Susie Wiles.

Yet it’s also possible, if less likely, that the plans were leaked in support of administration policy rather than out of factional infighting. Eliezer Marom argues that the leak was “part of the negotiations and serves to clarify to the Iranians that there is a real attack plan that Trump stopped at the last moment to conduct negotiations.”