Vladimir Putin has shown himself to be quite astute in establishing a Russian presence in Syria. After waiting for the Americans to make it clear that they did not intend to get involved in the fighting there, he moved into the vacuum quickly and massively. He has established Russian naval and air bases and has provided military support to Syrian President Bashar Assad. Having saved Assad from defeat, Putin became Assad’s patron.

Now Assad is indebted to Putin and relies on him for further military support, which includes Russian aircraft and missiles. The use of Russian mercenaries for fighting on the ground allows Putin to claim that no Russian ground forces are involved in the fighting and that the Russian military presence on the ground is limited to the Russian naval and air bases. The use of mercenaries is a ruse that was already used to cover the Russian involvement in Ukraine. Although quite transparent, it seems to be working. It has become part of the inventory of methods used to spread Russian influence beyond Russia’s borders. The world seems to be getting used to it.

Whether to his satisfaction or not, Putin has become an ally of the Iranians, who are also supporting Assad through Hezbollah as well as with Iranian forces on the ground. They have all well situated themselves in Syria.

On more than one occasion, Israel has made clear to Putin that it opposes the supplying of weapons to Hezbollah via Syria and that it is determined to keep Iranian forces from approaching Israel’s borders. Various arrangements have been made between Russia and Israel that are supposed to ensure the avoidance of conflict between Israeli aircraft operating over Syria and Russian aircraft. This seems to have worked so far.

Now Putin is now considering supplying S-300 surface-to-air missiles to Assad, which would provide the Syrian president with the ability to engage Israeli aircraft attacking targets in Syria. This could bring about a dramatic change in the situation in Syria, and is liable to increase the prospect of a direct conflict between Russia and Israel. From Putin’s standpoint, this is a gamble whose outcome is hard to predict.

Undoubtedly a few of the old-timers at the Kremlin remember the effect that the introduction of Soviet surface-to-air missiles in Egypt in 1970 had on the War of Attrition, and then during the Yom Kippur War, when they managed to neutralize the Israel Air Force. They probably hope that now the supply of the S-300 missiles to Syria will have a similar effect.

But they may also recall how, nine years after the Yom Kippur War, in the First Lebanon War, the Israel Air Force destroyed Soviet missile batteries deployed in Lebanon without losing a single aircraft. That time Soviet technology had met its match, and it was a blow heard around the world.

Is it possible that the Israeli Air Force will know how to deal with the S-300 missile system if it is deployed in Syria? That no doubt is of concern to Putin and his generals. Such a scenario is liable to constitute a harsh blow to Russian weapons technology, hurting the Russians’ marketing efforts for this missile system to other countries, such as Iran, and even raising questions as to the continued Russian-Iranian alliance in Syria.

For the first time since the beginning of the Russian intervention in Syria, Putin may find himself in direct confrontation with Israel. So far he has been able to maintain proper relations with Israel. Now it appears that he will have to make a choice.