For a while, Turkey and Israel were the unexpected couple, the increasingly Muslim state buying the Jewish state’s weapons and Israel offering Turkey a potentially strategic gas and oil pipeline.

That all changed when Israeli commandos raided the so-called Gaza Freedom Flotilla in May 2010 in international waters of the Mediterranean.

On one of the Turkish ships, the Mavi Marmara, Israeli Navy commandos faced resistance from about 40 of the 590 passengers. Some of the activists were armed with iron bars and knives.

During the struggle, nine activists were killed, including eight Turkish nationals and one Turkish American, and many were wounded.

That was a turning point in the relations between the two countries. But three years later, the two sides appeared to mend relations. In a half-hour telephone exchange between Israel’s Prime Minister Benjamin Netanyahu and Turkey’s then-Prime Minister Recep Tayyip Erdogan, the former apologized on behalf of his nation; Erdogan accepted the apology and both agreed to enter into further discussions.

On June 29, 2016 the agreement was finalized and approved by the Israeli government. Israel paid compensation to the families of the people that were killed.

But as the Syrian civil war spiraled out of control and Daesh swept across Iraq, other forces gathered to disrupt the relationship. As the US worked with Kurdish forces to help destroy Daesh, Turkey grew increasingly angry with the US and has edged closer and closer to Russia, raising fundamental questions about Turkey’s NATO membership. And, of course, Turkey has other interests in the Middle East. All this has helped poison relations between the two states. Today, distrust of Turkey is the norm among high-ranking officials in the Israel defense industries and in the defense establishment. “With Turkey’s new friends, we better stay aside,” one of them told Breaking Defense.

Another said: “We cannot trust Turkey now. Should this country be shown the way out of NATO? What is the alternative?”

In the golden years of Israeli-Turkish relations, the Israeli defense industries were sure that they were going to hit the jack pot. In April 2005, Israel Aircraft Industries (IAI) and Elbit Systems won a contract to supply medium endurance drones to the Turkish military. Turkey’s local industry would provide sub-systems and services amounting to 30 percent of the contract.

But at the same time Turkey tried to bolster its leadership role in the Arab world. As part of that effort Ankara decided to cut all government-based business deals with Israel – ending a formerly substantial trade in military equipment. By that time Turkey had purchased 10 Heron drones from Israel Aircraft Industries in 2010.

That was the last deal. Since then, Turkey has developed its own drone, the Anka. Experts say the design is based on the Israeli aircraft.

Other negotiations, that included the supply of a spy satellite and other systems were stopped.

Since relations with Israel grew frosty, Turkey, has appeared to treat its NATO membership with disdain.

It has committed to buying Russian S-400 anti-aircraft systems. Gallia Lindenstrauss and Zvi Magen, senior researchers from the Institute for National Security Studies (INSS) in Tel Aviv, say in a recent paper that Erdogan’s advance payment to Russia for the purchase of two S-400 air defense batteries strengthens Russia’s standing in the Middle East but predict Turkey is likely to remain a nominal NATO member for the foreseeable future.

Part of the reason behind Turkey’s move to buy Russian is that when it needed improved air defenses during both Gulf Wars and the Syrian civil war, it had to rely on other NATO members stationing Patriot batteries in Turkish territory. The researchers note that Turkish officials charged that it took NATO members too long to act. Turkish officials officials also chafed at restrictions on Turkey’s use and access to them.

Another sign of Turkey’s growing estrangement from NATO: in April 2009, Turkey and Syria held a joint military exercise – the first of its kind between a NATO member and a Russian-armed and trained client state.

Another proof of the increasingly close relations with Russia, more than 50 percent of a pipeline that will supply Turkey with Russian natural gas under the Turkish Stream project has been completed. The Turkish Stream project envisages the construction of two pipelines, each 939 kilometers long. The natural gas provided by the first pipeline alone will meet 35 percent of Turkey’s natural gas consumption.

Finally, Russian companies will build Turkey’s first nuclear power plant. Work begins this year, Erdogan said recently.

Policymakers are now wondering, among other concerns, how a NATO ally will simultaneously operate a Russian-made air defense system and the planned, US F-35 stealth fighters.

Countries in the region are acting to counter the Turkish moves. The defense ministers of Cyprus, Greece and Israel met in Athens late last year to discuss strengthening cooperation to promote security, stability and peace in the Eastern Mediterranean.

Cypriot Defence Minister, Christoforos Fokaides, said after attending the first meeting with his counterparts: “Our vision is to gradually turn the wider region from a conflict zone to an area of peace, stability and cooperation.”

Meanwhile, Israel is slowly building closer relations with NATO. Last month Israel signed a logistics agreement with the NATO Support and Procurement Agency (NSPA). The agreement is a breakthrough for Israeli companies in the cyber, optics, defense and software sectors. Israeli sources told Breaking Defense that they will allow Israeli companies to compete in NATO tenders and be part of NATO’s database of authorized exporters, thereby opening many doors to Israeli companies choosing to operate in this channel.

The sources added that while the tenders have great potential, NATO member countries have the right to ask that bids be restricted to defense businesses operating in NATO countries. Israel, which is not a NATO member, is a “non-NATO ally.”

Will that status change in the future ? In the fast moving geopolitical changes in this region and the wider world, it’s not impossible.