The White House’s decision to hire the elder Michael Flynn despite a series of red flags, and an explicit warning from Obama not to do so, raises serious and troubling questions about the Trump administration’s hiring process and about the president’s claims to hire the best people. Given his record and work, Flynn should never have been entrusted with the post of national-security adviser. But the misdeeds in question are mostly related to Flynn’s personal conduct—whether he failed to disclose or seek permission to receive moneys; whether he mingled his business interests with his government work.

These various stories about Flynn suggest a couple of tendencies. One was an entirely mercenary approach about his business partners, in which he was agnostic about who paid him and apparently eschewed due diligence about them. Flynn apparently had few reservations about where he was receiving income, as long as he was receiving it. Russia is an interesting case. Many Americans view Russia as a dangerous geopolitical rival (although the Obama administration attempted a failed “reset” in Russo-American relations), but while it does not explain or excuse failures to disclose under the law, Flynn had apparently decided that Russia was a prospective friend. “We have to figure out how to work with Russia instead of making it an enemy,” he told The New Yorker’s Nicholas Schmidle. But in the case of Turkey, Flynn abruptly switched his view on Erdogan, despite his longheld critique of Islamist politicians, when he started getting a paycheck.

The second tendency is that Flynn has mixed his work in government and his private-sector work, either intentionally or because of sloppiness. Perhaps Flynn, as a lifelong military officer, came to believe that as a loyal U.S. soldier, his own interests were inseparable from the national interest. But his lobbying on behalf of Turkey and his work on the “Marshall Plan” created perhaps irreparable conflicts of interest between his clients’ wishes and U.S. government policy, especially given his access to the country’s most closely guarded secrets.

Although the “Marshall Plan” provides yet another link between Flynn and Russia, if a tangential one, investigations into these matters veer toward the “red line” the Trump team has attempted to establish, insisting that although Mueller has the authority to investigate Russian interference in the 2016 election, the special counsel must not veer into private business dealings of the president or anyone else in his inner circle. In fact, as my colleague Adam Serwer drives home, Mueller has the authority to investigate more or less whatever he wants.

It’s easy to see why the president’s lawyers would attempt to direct Mueller and other investigations away from private business dealings, and also why the Flynn cases would be cause for concern. In his indifference to his business partners, and in his tendency to mingle personal and government work, Flynn resembles few people so much as Donald Trump himself. Trump has long shown little care for who his business partners are, taking a don’t-ask, don’t-tell approach whether dealing with American organized crime or associates of the Iranian Republican Guard. And Trump has steadfastly declined to remove himself from his business empire, leading to conflicts of interest and enrichment of his business properties. Trump might not be in the same sort of trouble that Flynn is right now, but the former aide offers a cautionary example.