Russian president Vladimir Putin made dangerous history in 2014. His invasion of Crimea and subsequent annexation of the peninsula shredded the diplomatic agreements stabilizing post-Cold War Eastern Europe.

Then Putin ignited a low-level war in Eastern Ukraine. Despite a September 2014 ceasefire agreement, Putin’s overt covert war-making continues in Eastern Ukraine. The Kremlin has concluded that Western leaders, European and American, are weak and indecisive.

Putin, unfortunately, knows how to use specific tactics in operations designed to achieve his strategic goals.

Military analysts typically recognize three levels of conflict: the tactical, the operational and the strategic. The categories are general, and distinctions often arguable. Firing an infantry weapon, however, is a basic tactical action. Assassinating Austrian royalty with a revolver is a tactical action, but one that in 1914 had strategic effect (global war). U. S. Grant’s Vicksburg campaign (1862-63) consisted of several Union military operations around Vicksburg (many unsuccessful). The campaign’s concluding operation, besieging Vicksburg, was an operational victory that gave the Union a strategic military and economic advantage: control of the Mississippi.

Putin’s Kremlin uses propaganda operations to blur its responsibility for tactical attacks in Ukraine. International propaganda frustrates Western media scrutiny of Russia’s calculated tactical combat action. Local propaganda targets Eastern Ukraine. Earlier this month, Ukrainian journalist Roman Cheremsky told Radio Free Europe that despite suffering criminal bullying by pro-Russian fighters, Kremlin “disinformation” is convincing Eastern Ukraine’s Russian speakers that Ukrainian forces are “bloodthirsty thugs.”

Cheremsky said that separatist fighters are preparing “for an offensive to capture more Ukrainian territory.” He saw “a vast quantity of weapons stored” in rebel camps, to include rockets “as well as tanks.”

The Radio Free Europe report indicates Putin used the last months of 2014 to prepare to wage a wider war in Ukraine in 2015.

The Kremlin mastermind, however, did not forsee the precipitous drop in oil prices.

Saudi Arabia decided to keep pumping oil for several reasons, to include demonstrating to the U.S. that it has the power to undercut the price sustaining U.S. oil and natural gas “fracking.” The Saudis want to remind America that they still matter. The Saudis also have another strategic goal. Low oil prices damage the regime the Saudis see as their biggest threat: Shiite Iran’s theocratic dictatorship. Low oil prices could crimp Iran’s nuclear weapons program.

Oil’s price plunge, however, has also slammed Putin, threatening the genius with political and economic problems that, if prices remain low, could erode his personal political power. Energy revenue declines do far more damage to Putin than the economic sanctions Western governments have imposed.

So what’s a brilliant, innovative, thoroughly unscrupulous and utterly amoral strategist to do?

According to the AP, this week (Jan. 20), Iran and Russia signed “an agreement to expand military cooperation.” Iran and Russia are old antagonists, but given current circumstances vis a vis the U.S. and Saudi Arabia, Tehran and Moscow may be following an old Machiavellian adage: “the enemy of my enemy is my friend.” The deal includes counter-terror cooperation, military training and “enabling each country’s navy to use the other’s ports more frequently.”

For years Iran has sought Russian air defense weapons, presumably to thwart a U.S. strike on its nuclear facilities. However, the agreement’s naval port clause attracts my interest. About a third of the globe’s exported oil moves on tankers through the Persian Gulf’s Indian Ocean outlet, the Strait of Hormuz. To spike oil prices, Iran often threatens to close Hormuz. If Iran actually tried to shut the Strait, Western nations have assured Gulf Arab oil producers that they will respond militarily.

Here’s a discomfiting speculation. Putin could complicate a Western response by suggesting Russian warships will defend Iranian ports against all “aggressors.”

Here’s a darker speculation cast as a question. Would a desperate strategist encourage Iran to fight a proxy war against Saudi Arabia or a smaller Gulf Arab producer?

Putin’s Crimean invasion and annexation were desperately bold actions. The price plunge has exposed his regime’s strategic weakness: dependency on oil revenue.

They play chess in Russia, don’t they?

Austin Bay is a syndicated columnist.

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