It was supposed to be a triumphant year for White House Senior Adviser Jared Kushner. Part of the team that guided his father-in-law to victory in 2016, the young Kushner was catapulted into the highest echelons of power.

He was handed a broad portfolio that included making peace in the Middle East and was reportedly a key part of Trump’s inner circle and decision-making team. But as 2017 dragged on, the man known as Mr. Perfect had anything but a perfect year.

Here are Kushner’s worst moments from 2017:

The Flak Jacket/Blazer/Khakis Iraq Chic

When Kushner visited Iraq in April, he obviously did not want to abandon his dedication to preppy style. But the image of the senior adviser sporting a flak jacket (with “Kushner” scrawled on it), along with a blazer and khakis, brought on a torrent of mockery.

This pic of Jared Kushner in Iraq with a military bullet-proof vest over his usual Thurston Howell III outfit really says it all pic.twitter.com/Qbt90NiqV4 — Amy Westervelt (@amywestervelt) April 6, 2017

Kushner Companies Under Investigation for Use of ‘Immigration-for-Investment’ Scheme

Although Kushner stepped down as head of Kushner Companies in January, his real-estate firm gave him a number of headaches throughout 2017. Perhaps the biggest one was its use of the EB-5 visa program, which allows wealthy investors to gain visas in return for investing in the U.S.

Kushner’s sister, Nicole Kushner Meyer, made a pitch to Chinese investors for a New Jersey development and teased green cards. An ad for the event reportedly said, “Invest $500,000 and immigrate to the United States.”

The Kushner family later apologized for mentioning the connection to the Trump administration in the pitch.

But federal investigators are also reported to be interested in Kushner Companies’ use of the scheme, subpoenaing documents in May. It was not clear what potential violations were being investigated, according to the Wall Street Journal.

Jared Scales Back Role After Bad Advice, Failures

Jared and Ivanka are reported to be scaling back their roles in the White House after officials have become annoyed by their presence. The move came shortly after Trump’s decision to back Sen. Luther Strange in the Alabama Senate primary backfired spectacularly and Strange was crushed by conservative challenger Judge Roy Moore. Kushner was widely believed to have been a key voice in urging Trump to get involved in the race and back Strange—a decision Trump himself admitted may have been a “mistake.”

Kushner was also widely reported to be a key official encouraging President Trump to fire FBI Director James Comey—a move which has since turned out to be seen as a mistake as it directly led to the appointment of FBI Special Counsel Robert Mueller, whose probe has dogged the Trump administration throughout 2017.

Additionally, while Ivanka and Jared were both hoped by liberals to be a “moderating” influence on Trump on items such as LGBT rights and the Paris climate deal, that has not come to pass.

Axios cited “the couple’s friends,” as saying that the pair sees themselves as under constant attack and that they have never planned to stay four years in the administration, hinting a departure could be imminent in 2018.

Mueller’s Probe Eyes Kushner

FBI Special Counsel Robert Mueller’s appointment was announced in the wake of the firing of FBI Director James Comey—a decision reportedly backed by Kushner. But as the probe has gone on, Kushner has apparently become a key figure for Mueller.

Kushner was part of a 2016 meeting between Donald Trump Jr. and a Russian lawyer at Trump Tower—a meeting which Trump Jr. said he took as it promised information that would “incriminate” Hillary Clinton.

Kushner was questioned by Mueller’s team in November, during which he reportedly answered questions about a meeting with the Russian ambassador during the transition. It later emerged that Kushner was the “senior Trump official” who directed former National Security Adviser Michael Flynn to contact the ambassador about a U.N. vote on Israeli settlements.

While it is not clear if the Mueller team believes Kushner did anything wrong, Mueller’s interest in him has no doubt led to a tough 2017 for Kushner.

Congress Gets Angry with Lack of Disclosure

Kushner spent much of 2017 aggravating congressional lawmakers with his lack of disclosure about his foreign contacts and other information deemed important—particularly over various investigations into alleged Russian interference in the 2016 election.

Two Senate committees have complained about his failure to hand over certain documents, and that they have learned certain details from the media. Lawmakers on the Senate Intelligence Committee were angered in September when they discovered from media reports that Kushner used a private email account occasionally for White House business.

Lawmakers on the Senate Judiciary Committee wrote to Kushner’s lawyer in November, saying the document collection he provided to the committee was incomplete.

Newsweek reported in December that Kushner is still using an interim security clearance after he initially omitted dozens of foreign contracts from his original form submission for clearance.

Disastrous Real Estate Deal Comes Under Scrutiny

In 2006, at the height of the real-estate bubble, Kushner’s real-estate firm made an audacious purchase of 666 Fifth Avenue—prime Manhattan property. But just over 10 years later, that deal has reportedly crippled the company and has raised significant questions about Kushner himself.

An in-depth article by Bloomberg News in August gave a dour view of the purchase:

It was 2006—the height of the real-estate market boom—when Kushner Cos. agreed to buy 666 Fifth Avenue for $1.8 billion, then a record for a Manhattan building. All of it was borrowed except for $50 million. The company still holds half of a $1.2 billion mortgage, on which it hasn’t paid a cent. The full amount is due in February 2019.

In addition to a number of detailed studies of the implications of the deal, Congressional Democrats have started asking questions about a potential conflict of interest and sent a letter to Kushner expressing concerns about reports that 666 Fifth Avenue is in need of “massive cash bailouts” from foreign nationals. Kushner Companies has disputed such descriptions of the situation as inaccurate.

Kushner did not answer questions about whether he had done anything “related to helping finance, purchase, or assist with the debt.”

“These are straightforward questions, but we still haven’t received an answer. What is Mr. Kushner hiding?” Rep. Ted Lieu (D-CA) said in a statement.

Kushner Gets Teased by Billionaire Haim Saban

Kushner took part in a Washington, DC, forum in December featuring Israeli-American billionaire mogul Haim Saban, and ended up being teased for his efforts to make peace in the Middle East.

“But to achieve [stability in the Middle East], the team has in it an entrepreneur, you, a real estate lawyer, a bankruptcy lawyer—I don’t know how you’ve lasted eight months in this lineup but that’s for another day—and it’s impressive that it’s still going,” Saban said.

With almost a year into peace efforts, and few tangible results, Saban asked the question on many people’s minds. “How do you operate with people who basically, with all due respect, a bunch of Orthodox Jews who have no idea about anything,” Saban said. “What are you guys doing? Seriously, I don’t understand this.”

“I’ll definitely say it’s not a conventional team,” a smiling Kushner responded.

Adam Shaw is a Breitbart News politics reporter based in New York. Follow Adam on Twitter: @AdamShawNY.