Donald Trump has a staffing problem. His Department of Homeland Security has no political appointee at the helm and hasn’t since July. His Health and Human Services Department is now also absent leadership. The president’s chief strategist is gone, too, and Trump seems in no rush to replace any of them. Now, Trump’s Secretary of State is reportedly in hot water with his boss and may be next in line for the block. It’s no wonder then that, despite the endless cascade of embarrassments he has caused his father-in-law, Jared Kushner remains firmly ensconced in his position in the White House.

Considering the comically expansive list of responsibilities heaped on Kushner’s plate by the president, you can understand why Trump would be reluctant to jettison his senior advisor. Kushner is effectively a shadow secretary of State, maintaining back channels with Beijing, Moscow, and Mexico City. He is responsible for reigniting the Israeli-Palestinian peace process. He is in charge of mitigating the effects of America’s sprawling opioid crisis. He’s supposed to design and implement a plan to streamline the entire executive branch, and he is tasked with compiling criminal justice reform recommendations. You could be forgiven for thinking Kushner has become a magnet for jobs no one wants.

If nothing else, the Herculean labors that are Kushner’s charge suggest that Trump has a great deal of faith in his daughter’s husband, but it’s a wonder as to why. For months, Kushner has been the source of a series of humiliations that only reflect poorly on Donald Trump and his presidency.

Even as the president complains to anyone willing to listen about the deleterious effect the leaks out of his administration are having on his government, reporters somehow manage to know precisely what Kushner and his wife are thinking at any given moment. The leaks from people “close to” Kushner or “familiar with the thinking” of the first daughter and her husband, particularly during challenging news cycles for Trump, has become a punchline. Kushner’s leaks aren’t just self-serving; they’re also humiliating for the president. In an off-the-record conversation between Kushner and a group of congressional interns leaked to Foreign Policy¸ Kushner insisted that the Russian collusion narrative was bunk if only because the Trump campaign was too inept to carry out a sophisticated operation like that.

Kushner was forced into issuing that cringe-inducing mea culpa as a result of his own poor judgment. It had been recently revealed that he took an ill-advised 2016 meeting with an attorney who was almost certainly a cut-out for the Kremlin, which was seeking ways to influence and compromise Trump campaign officials. This was one of many revelations that compelled Kushner to revise his financial disclosure forms, where he declined to inform background investigators of his contacts with individuals likely linked to the Russian government.

The president’s right-hand man reportedly supported the firing of James Comey, which Steve Bannon accurately described as the worst political blunder in modern American history. That forced the appointment of a special counsel and has created a cloud over the administration, to say nothing of the cost to its members now that they must retain counsel at their own expense. What’s more, the camp that backed Comey’s dismissal thought Democrats would not react to it because to do so after how often they had criticized the former FBI director would be hypocritical. Any political strategy that hinges on your opponents observing perfect consistency is naïve to the point of delusion.

Finally, and most critically, Kushner’s ethical lapses are now becoming a political liability. This week, both Kushner and Ivanka Trump were fined $200 for missing deadlines to submit financial disclosure forms as mandated by ethical guidelines. This is the second such fine for Kushner, whose situation is especially thorny due to his sprawling real estate business and the myriad financial entanglements from which he was obliged to divest to assume his role in the White House. This wouldn’t be of much note save for the fact that it creates the impression that Kushner is not ethically diligent, and that could become a major problem considering his latest infraction.

In late September, Kushner confirmed the accuracy of investigative reporting that alleged he had been carrying out correspondences with White House officials pertaining to government-related business over a private email account, which is a violation of federal records-keeping laws. But within days of the discovery of Kushner’s private White House business-related emails, a USA Today investigation alleges, he moved that email account over to a Trump Organization email server. That’s right: Kushner has been conducting America’s business over a private email server. Whether the public comes to see these moves as an effort to evade scrutiny is a matter of perception, and the president’s senior advisor’s conduct has not inspired confidence.

By all accounts, the president values loyalty and is himself loyal to a fault. Perhaps there is no threshold at which Kushner becomes a liability in Trump’s eyes. The president and his advisors reportedly see Kushner as an invaluable diplomatic asset, particularly among the Middle East’s Sunni states, which have warmed to this administration in a way they did not to its predecessor. That seems more a function of Donald Trump’s hostility toward the Iran nuclear accords and the leverage they afford the Shiite-led Islamic Republic than Kushner’s ambassadorial aplomb. Nevertheless, whatever his value to Trump may be, Kushner is nearing a point at which the political risks of his association with the president outweigh the benefits. Both Trump and his son-in-law need to start thinking about what happens when that tipping point is reached.