President-elect Donald Trump has tapped ExxonMobil CEO and chairman Rex Tillerson to be his secretary of state, he confirmed early Tuesday.

Tillerson’s nomination as Washington’s top diplomat and the primary conduit between the United States and foreign governments has drawn criticism from those worried about his connections to Russian President Vladimir Putin.

The photos below illustrate the evolution of Tillerson’s relationship with Putin, beginning after Exxon struck a deal with Russian state-owned oil giant Rosneft in 1999 and ending with Putin awarding Tillerson Russia’s Order of Friendship medal in 2013.

Tillerson initially met Putin in 1999 on the Sakhalin island in Russia’s Far East, when Exxon struck a deal with Russian state-owned oil giant Rosneft. The two men have met a number of times since then, as Tillerson continued building a relationship with Putin through his business interests in Russia.

Foto: Vladimir Putin, 5th left, seen during his meeting with U.S. oil business top executives in Washington, Friday, Sept. 16, 2005. Tillerson is first from the left. source AP

In 2011, Exxon signed another deal with Rosneft for a lucrative $3.2 billion oil deal that would give Exxon permission to develop offshore oil fields in the Russian Arctic in exchange for Rosneft getting stakes in a number of Exxon’s US-based projects.

Foto: source AP

Putin shakes hands with Tillerson after their meeting in the Novo-Ogaryovo residence outside Moscow, Monday, April 16, 2012.

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Foto: source AP

Rosneft and Exxon were enthusiastic about the deal and expanded it in 2013. But it was canceled one year later, when the US imposed sanctions on Russia over its annexation of Crimea and invasion of Eastern Ukraine. Tillerson sharply condemned the sanctions, saying they caused “broad collateral damage.”

Foto: Vladimir Putin and Rex Tillerson shake hands at a signing ceremony of an agreement between state-controlled Russian oil company Rosneft and Exxon Mobil corporation at the Black Sea port of Tuapse, southern Russia, Friday, June 15, 2012. source AP

Source: Politico

Critics have expressed concern over Tillerson’s nomination because of potential conflicts of interest. One of the first issues on Tillerson’s agenda, for example, may be weighing whether to lift sanctions on Russia. Tillerson currently holds $151 million in Exxon stock, and the value of that stock would increase if sanctions were lifted.

Foto: source AP

In 2012, Putin presented Tillerson with a Russian medal at an award ceremony of heads and employees of energy companies at the St. Petersburg economic forum in St. Petersburg, Russia.

Foto: source AP

Putin even personally awarded Tillerson with Russia’s Order of Friendship medal in 2013, the highest honor bestowed on foreign citizens. It is given to foreigners whom the Russian government believes have helped Russia and its people.

Foto: Putin and Tillerson smile during a signing ceremony in the Black Sea resort of Sochi, Russia, Tuesday, Aug. 30, 2011. source AP photo/RIA Novosti, Alexei Druzhinin, pool

Source: ExxonMobil