Diplomacy is not a transactional affair. This seems lost on self-proclaimed Middle East expert and presidential son-in-law Jared Kushner. The ever-increasing number of questionable business entanglements between Kushner’s family and Israeli companies, individuals and government ministers is troubling given his directive to honestly broker an equitable peace agreement between the Israeli government and the Palestinian Authority. That and his lack of experience in government, politics or international relations.

On the eve of his inauguration, Donald Trump told supporters if Jared “can’t produce peace in the Middle East, no one can,” and that he thought his son-in-law was going to do “a great job.” Yet Jared’s only prior job experience came after his father, Charles Kushner, was sent to prison for making illegal campaign contributions, tax evasion and witness tampering. Jared assumed control of the Kushner Companies, his family’s real estate business, during his father’s absence. He also personally acquired an unprofitable weekly newspaper, widely viewed as a vanity project.

Jared’s subsequent misadventures included the purchase of 666 Fifth Avenue, a mid-town Manhattan office building that has been teeter-tottering on the brink of disaster for quite some time. The overleveraged property left him scrambling for funds prior to his father-in-law’s election to avoid default on a $1.2 billion mortgage — half of which is owed by the Kushner Companies.

One month before Trump’s victory, Deutsche Bank came to the rescue with a $285 million loan to the Kushner Companies. This was a year after the bank had been fined $425 million by the New York State Department of Financial Services for its involvement in Russian money-laundering. While Jared’s relationship with Deutsche draws scrutiny with every passing day, his activities in Israel are more concerning as they relate to his role as diplomat.

Many of the characters with whom the Kushners have dealt in the past have somewhat shady reputations. They include Israeli billionaire Beny Steinmetz, currently facing criminal probes for bribery and corrupt practices in Israel, the United States, Switzerland and Guinea. Steinmetz engaged in real estate transactions with the Kushners in 2012. Then there was a 2015 New York real estate deal between the Kushner Companies and Uzbek-born Israeli citizen Lev Leviev, one of the wealthiest men in the world, who has also identified himself as a “true friend” of Vladimir Putin.

Last May, Israeli insurance company Menora Mivtachim, invested $30 million in Kushner Companies-owned apartment complexes in Maryland. The cash infusion occurred just prior to Jared Kushner’s first diplomatic mission to the Middle East.

Kushner family ties to Israel don’t stop there. In the last decade, the family’s foundation funded Israeli settlements and organizations on the West Bank. Jared served as the foundation’s co-director during that period. The settlements were considered illegal under international law, yet the Kushners continued to support them.

Many also consider the Kushners’ relationship with Israeli Prime Minister Benjamin Netanyahu — no stranger to legal scrutiny himself — suspect. Multiple news sources have reported that before Charles Kushner entered prison, the prime minister had identified him as a potential donor to Netanyahu’s Likud Party. The New York Times noted that Netanyahu had slept in Jared Kushner’s room while on a visit to the Kushner family home. Jared, then a teenager, was relegated to the basement. Politics does make for strange bedfellows.

How can Jared Kushner possibly negotiate a legitimate deal between the Israelis and Palestinians when he maintains personal ties to one of the parties at the table? There are too many appearances of impropriety and corruption to suggest he is capable of effectively carrying out his father-in-law’s mandate. While bad business practices and suspect transactions are harmful only to those involved and their investors, failed transactions of a diplomatic nature can prove disastrous.

Entrusting the fate of both the Israeli and Palestinian people, as well as a multitude of other nations in the region, to Jared Kushner is more than a risky undertaking. It is dangerous.

Blair Bess is a Los Angeles-based television writer, producer, and columnist. He edits the online blog Soaggragated.com, and can be reached at BBess.soaggragated@gmail.com.