The 5 Worst Business Deals of 2016
Yahoo's hack problem just got worse. · Fortune

Perhaps it was Donald Trump, or Bernie Sanders, or all the uncertainty around the election. Or maybe it was the Federal Reserve and the fact that interest rates began to rise. Whatever the reason, even the stock market’s march to Dow 20,000 wasn’t enough to the keep the business world’s deal juices flowing. For mergers and acquisitions, and for initial public offerings in particular, 2016 was a flop.

U.S. M&A volume dropped 21% from the previous year. In terms of dollars raised, it was the lowest year for IPOs since 2003, and the second-lowest year since 1992.

But even through there were fewer deals, there were still a fair share of ones that should never have been announced in the first place (we’re looking at you, ), along with a couple from past years whose glaring flaws undid them this year. Here are Fortune’s picks for the dumbest deals of 2016.

Verizon-Yahoo

Even before news surfaced that Yahoo had been the victim of two massive hacks, Verizon looked to be overpaying for the fallen king of email. The $4.8 billion bid, announced in July, values Yahoo at 5 times cash flow. That’s not a lot for a tech company. Even troubled Twitter , for instance, trades at 15 times cash flow. But Twitter is still growing. Yahoo is not.

The once-wunderkind CEO Marissa Mayer has spent the past four years trying to turn the company around--streaming football games and hiring big-name journalists like Katie Couric. It hasn’t worked. Yahoo’s core business lost $2.4 billion in value under Mayer. And cash flow is down to just over $800 million, from $1.5 billion in 2012.

Verizon, of course, thinks it can stop the decline, perhaps by combining Yahoo with AOL, which it bought in 2015, to create a competitor to or Facebook . But YahoOL has a lot of catching up to do. And now the hacking news has soured Yahoo’s main asset--secure, non-work email. Verizon is already trying to renegotiate its buying price. The market thinks it will cut its bid for Yahoo by $1 billion. That may still mean it’s paying $3.8 billion too much.

Every Deal Ever Done by Time Warner’s Jeff Bewkes

CEO Jeff Bewkes has long been wheeling and dealing atop the media giant, culminating in this year’s proposed mega-merger with AT&T. Only in 2016, though, did it become clear how truly dumb Bewkes’s previous deals have been.

Both AOL and Time Warner Cable soared in value after Bewkes spun them off in 2009. Time Inc. , the parent company of Fortune, has dropped in value after being similarly cast aside in 2014, so jettisoning it perhaps saved Time Warner shareholders some money–but not nearly enough to make up for how much they’ve missed on Bewkes’ other spin-offs.