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If wearing a corporate T-shirt meant anything, T-Mobile US CEO John Legere would have had his merger with rival Sprint in the bag months ago.

But it doesn’t, and the electric-magenta T-shirts, which Legere, with his shoulder-length locks and tired eyes, wore even to a recent Congressional hearing, came across as just another attempt to convince the powers-that-be that this megadeal was a good idea.

The proposed $26.5 billion merger—$59 billion with debt—between T-Mobile US (TMUS) and Sprint (S) staggers along, now a year since it was announced. As merger arbs know, time is rarely a friend of M&A. The longer it takes, the likelier something goes awry: markets, the economy, the business, belief. Assets waste. Talent leaves. Stocks fall.

On March 29, the stock market woke to this reality. Investors pummeled shares of Sprint and T-Mobile (though Verizon Communications (VZ) also got hit). One catalyst: A report by Dealreporter.com that 18 state attorneys general, led by New York, were preparing to oppose the deal.

Investors were spooked again after The Wall Street Journal reported on April 16 that the deal was meeting resistance with antitrust officials at the Justice Department. That report sent T-Mobile stock down 2.7% in pre-market trading the next morning, while Sprint stock dropped 4.6%.

How has T-Mobile and Sprint gotten so hung up?

The transaction was always a long shot. Clearly, Legere made the calculation that rather than fight it out on unfavorable antitrust grounds, he would tailor an argument for this Make America Great Again moment. For a year now, he has made an escalating series of promises about providing broadband for rural America, increasing, not cutting, jobs, agreeing to no price increases for three years, and taking an anti-China, no-Huawei 5G stance that aligns him with the president’s belief that U.S. domination of 5G is a national security imperative.

The irony is that unlike Verizon and AT&T (T), the top two wireless incumbents, both Sprint and T-Mobile have foreign ownership. SoftBank of Japan (9984. Japan) controls Sprint while Deutsche Telekom (DTE. Germany) owns T-Mobile. If the deal is approved, Deutsche Telekom will control 42% of the new company and appoint six seats on the board; SoftBank will get 27% and four seats.

Not a lot has gone right. As the Washington Post reported, nine T-Mobile executives booked rooms at Trump’s Washington hotel the day after the deal was announced in April—they wandered around in those T-shirts—and the company spent more than $195,000 there over the next 10 months.

T-Mobile’s parent, Deutsche Telekom, hired a firm run by Corey Lewandowski, Trump’s former campaign manager, to lobby for the deal, which echoed AT&T’s hiring of Trump’s lawyer and fixer, Michael Cohen. None of this is illegal, but it was bound to inflame already entrenched opposition.

In December came some good news. The deal got a green light from the Committee on Foreign Investment in the U.S., or Cfius, and an interagency group called Team Telecom, which the White House has empowered to monitor transactions involving technology and foreign ownership—mostly from China. In 2018 Trump famously killed the $117 billion Broadcom (AVGO) offer for Qualcomm (QCOM); Broadcom was based in Singapore—not China, but in the neighborhood.

More recently, Cfius reportedly told Beijing Kunlun Tech that it had to divest gay dating app Grindr that it bought in 2016 for $98 million. The reason, wrote law firm Morrison Foerster in a note: concerns that the Chinese government could collect and exploit information on U.S. citizens.

The Federal Communications Commission, meanwhile, has been a slog. The FCC’s 180-day deal “shot clock” has been stopped and started three times, once for the government shutdown. The clock was stopped most recently on March 7, when T-Mobile submitted a 63-page addendum on wireless home broadband, which required a comment period. The new filing suggested that T-Mobile needed to buttress its case. The clock began ticking again on April 4 at Day 122.

That means there is roughly two months left, plus probably a few months after that, even if the FCC clears the deal. T-Mobile had predicted that approval would come in the first half of the year. Now it looks like summer, at best.

The deal’s biggest hurdle might be the Justice Department’s antitrust division, which recently lost a brutal battle with AT&T over its merger with Time Warner.

Here’s where things get particularly complicated and weird. Justice tried to block AT&T’s vertical merger with Time Warner—two companies in different, if related, businesses—arguing the kind of case that hadn’t been pursued in decades. T-Mobile and Sprint, by comparison, is a horizontal merger—both in the same industry—that will reduce the number of wireless providers to three from four.

Normally, that would, at best, provoke a long look from antitrust agencies with likely structural remedies such as divestitures, or at worst, reject it—as the Obama administration did in the two companies’ 2014 merger attempt.

This is also where time and politics intersect to form a quagmire. The deal has dragged on for so long that the 2020 campaigns have begun. Cries to reinvigorate antitrust have emerged among Democrats, and may have stirred up the state attorneys general. Democrats now also control the House of Representatives.

Makan Delrahim, the head of DOJ’s antitrust division, has had to fend off charges that Trump interfered in the AT&T case to punish CNN. He denies it, but would he want to revisit those charges by approving a technically more problematic horizontal merger?

T-Mobile seems to believe that its best chance is to wrap itself in 5G. Legere reiterated to Congress in March that prices would fall, contrary to Antitrust 101. His reason: The deal would mean the new T-Mobile could invest billions in a vast 5G rollout plan that would undercut monopolistic cable companies and force Verizon and AT&T to compete on price. Better yet, the 5G plan would also allow America to catch up with China in 5G. Nearly everyone would get more for less.

In March, Legere met with Delrahim, where he apparently made that case; Delrahim reportedly said he was “open” to the 5G argument, although around that time he noted that the European Union was right to block a merger between Siemens (SIE. Germany) and Alstom (ALO. France) to create the world’s largest rail company—a horizontal merger, albeit an industrial one. As for the FCC, Chairman Ajit Pai described 5G at a September 2018 White House summit as a “national imperative for economic growth and competitiveness.” The big question for both is whether T-Mobile’s 5G vision means that national security, however flexibly defined, trumps traditional regulatory norms.

Legere may get his merger. But if he does, he may find himself constrained by promises he’s had to make. Synergies will be harder to extract; other 5G players, like Verizon, which just launched a nascent 5G pilot in two cities, will have advanced. He and his shareholders better hope 5G is as magically transformative as he claims.

Write to Robert Teitelman at bob.teitelman@dowjones.com