The bankruptcy lawyer and son of an Orthodox rabbi is believed to be everything Obama is not: a fervent supporter of Israeli settlements, opponent of Palestinian statehood and unrelenting defender of Israel's government. So far to the right is Friedman believed to be that many who portend to be Israel supporters, particularly those on the far left of the political spectrum such as groups like J Street, worry he could push Israel's Prime Minister Benjamin Netanyahu further right, thus risking the peace process all together.
The heated debate over Friedman's selection is playing out just as fresh tensions erupt between the US and Israel.
In a decision that shocked many on Friday, the Obama administration moved to allow the UN Security Council to pass a resolution condemning Israeli settlements as illegal, including those in eastern Jerusalem. The move to abstain, rather than veto, defied years of US tradition of shielding Israel from such resolutions, and elicited condemnation from Israel, lawmakers of both parties, and especially Trump.
"Things will be different after Jan. 20th," when he's sworn in, Trump vowed on Twitter.
Presidents of both parties have long called for a two-state solution that envisions eventual Palestinian statehood, and Netanyahu says he agrees. Friedman, who still must be confirmed by the Senate, does not. He's called the two-state solution a mere "narrative" that must end.
Under Obama, the US has worked closely with J Street, an Israel advocacy group sharply critical of Netanyahu. Friedman accuses Obama of "blatant anti-Semitism" and calls J Street "worse than kapos," a reference to Jews who helped the Nazis imprison fellow Jews during the Holocaust.
For decades, the US has opposed Israeli settlement-building in lands it seized in the 1967 Six-Day War. Friedman runs a nonprofit that raises millions of dollars for Beit El, a settlement near Ramallah. Beit El runs a right-wing news outlet and a yeshiva whose dean has provocatively urged Israeli soldiers to refuse orders to uproot settlers from their homes.
So it's unsurprising that Friedman's nomination has already sharpened a growing balkanization of American Jews, between those who want the US to push Israel toward peace and those who believe Obama's approach abandoned America's closest Mideast ally.
It's a debate playing out even at Temple Hillel, near the Long Island-Queens border, where Friedman's father was rabbi for almost half a century.
"Clearly, David's opinions do not appeal to everybody in the synagogue, and they appeal to others in the synagogue," said Ken Fink, the synagogue's president and longtime congregant. "But there's a huge amount of pride for the hometown boy."
Thirty-two years before Trump's election, President Ronald Reagan donned a yarmulke and noshed on chicken cutlets and noodle pudding at Rabbi Morris Friedman's home, after a speech at Temple Hillel affirming the separation between church and state. Coming just two weeks before Reagan's re-election, the attempt to woo Jewish voters struck some as opportunistic, and they protested on the streets of the heavily Jewish town of North Woodmere.
Seated at the Sabbath table with Reagan was David Melech Friedman—his middle name means "king" in Hebrew. The rabbi's son went on to become Trump's bankruptcy lawyer, an advocate for right-wing policies on Israel, and now, Trump's choice for ambassador, despite having no diplomatic experience.
Cindy Grosz, who said she's known Friedman for nearly 50 years, recalled big parties with boisterous debates about Jewish issues held in his family's sukkah, the outdoor hut Jews build during the harvest festival Sukkot.
"He still has the same best friends he's had for over 30 years," Grosz said.
At his midtown Manhattan law firm, Friedman opens his offices to those in mourning who need a minyan—a quorum of 10 men in Orthodox Judaism—to say the Mourner's Kaddish, a prayer that observant Jews say daily for one year after a parent's death.
And it was a parent's death, in a way, that brought Friedman and Trump closer together. Over the years, Friedman has told friends the story of how the billionaire real estate mogul defied an oppressive snowstorm that had kept others away to "sit shiva" for Friedman's father during the Jewish mourning period.
Educated at Columbia University and NYU School of Law, Friedman developed a reputation as an aggressive, high-stakes bankruptcy attorney, representing Trump when his Atlantic City casinos went through bankruptcy.
In the courtroom, he's known as a formidable opponent, said attorney Tariq Mundiya, Friedman's adversary in several cases. He said he'd been aware of Friedman's advocacy on Israel but added, "When you're in the fog of war with David, the last thing you're talking about is the Middle East."
Enraged by Trump's pick, left-leaning groups and Palestinian officials have suggested his confirmation could spell the end of any serious discussions about peace.
Netanyahu has stayed publicly quiet about Trump's pick. Friedman and Trump's transition team didn't respond to requests for comment.