For all of his adult life, and probably a good portion of his childhood, Donald Trump has been telling people he’s a genius businessman, a habit he continued to great effect on the campaign trail. “We need a leader that wrote The Art of the Deal,” he said while announcing his candidacy in 2015. “I’m a negotiator. I’ve done very well over the years through negotiation,” he claimed during a Republican debate in 2016. As president, Trump told voters, he would rip up existing agreements his loser predecessors had struck and use his singular set of skills to forge new, better (bilateral!) deals for the U.S., just like he had done over the course of his career. Unfortunately, the 45th president has hit a couple major roadblocks in his attempt to do so—stemming primarily from the fact that he is actually a terrible negotiator who hasn’t struck the kind of deal he spoke about on the campaign trail in some four decades.

All this is worth remembering as America’s allies retaliate against Trump’s new tariffs on steel and aluminum, which he aimed at China but somehow ended up hitting Canada, Mexico, and Europe, too. And it makes complete sense when you consider the actual arc of Trump’s history as a real-estate developer. Indeed, as reporter Michael Kruse writes in a new piece for Politico, any successes Trump had in business occurred at the very beginning of his career, including the conversion of the Commodore Hotel to the Grand Hyatt at Grand Central and the building of Trump Tower. In those deals, according to Politico, he demonstrated a modicum of “salesmanship, verve, cunning, and good timing.” But his discipline and focus started to dry up shortly after those transactions and, hilariously, around the time he agreed to write a book called the The Art of the Deal, striking a comically awful agreement—for him—with ghostwriter Tony Schwartz, who said that Trump “basically just agreed” to all of his demands, including “an almost unheard-of half of the $500,000 advance from Random House and also half of the royalties.” (“What should have been a great deal on a book about negotiation actually is one of the most interesting pieces of evidence that he’s not a good negotiator,” Harvard Business School professor Deepak Malhotra told Politico, noting that Schwartz got his name on the cover in the same size text as Trump’s. “I don’t think there’s a better ghostwriting deal out there.”)

Other cringeworthy deals at the time included Trump’s acquisition of the Plaza Hotel for $60 million more than even the highest estimates said it was worth (“How can I live without it?” he reportedly said out loud during the negotiation); the acquisition of the Eastern Air Lines Shuttle for, again, some $60 million more than it was thought to be worth; and his overpaying for football players as a team owner in the doomed United States Football League. Then, of course, there was his fateful 1988 acquisition of the casino that “quickly would become the debt-bloated Trump Taj Mahal.”

From there it was onto the bankruptcy-happy 90s, thanks to the debts he racked up in the 80s—which Trump, naturally, has now tried to spin as evidence of his business savvy. That period included a deal to build apartments on the Upper West Side, in order to avoid personal bankruptcy, in which he “pretty much gave in to whatever [neighborhood groups] asked for,” according to a Trump Organization vice president at the time. That era was followed by the fake-businessman era, in which Trump played a successful negotiator on TV but, behind the scenes, had mostly given up on big deals in favor of licensing arrangements. “Negotiations increasingly were for comparatively uncomplicated branding and licensing agreements,” Kruse writes, “in which others did the harder legal work while he put his name on labels and made promotional appearances.”