One evening in August, executives at EchoStar and SpaceX retreated to a private room at a Del Frisco's, an upscale chain steakhouse in suburban Denver, a few miles from the EchoStar headquarters.

Rather than merely relax and enjoy dinner after a day of deal negotiations, the group was glued to a video screen of what would be a flawless launch of a SpaceX Starship occurring 1,200 miles away on the south Texas coast.

Less than two weeks later, the companies announced a landmark transaction between two tycoons that seemed impossible to fathom just a few months before. Elon Musk's SpaceX agreed to pay $19bn, in the form of cash, its private shares and future EchoStar debt service, in exchange for wireless communications spectrum previously belonging to EchoStar, the satellite operator founded by Charlie Ergen 45 years ago.

SpaceX had long coveted the spectrum cache as part of its efforts to commercialise its Starlink internet service.

For Ergen, the deal capped a remarkable comeback. Over the past 20 months, EchoStar had dodged bankruptcy twice, separately beating back Wall Street vulture funds and the Trump administration. The company's stock price has risen from $10 per share two years ago to more than $80 last week, amid more than $40bn in dealmaking.

Echostar's once deeply distressed debt has now rallied to par and its market capitalisation, in less than two years, jumped from just a few billion dollars to $25bn, one the most stunning corporate turnarounds in recent history.

Ergen -- whose personal stake in EchoStar has soared from just over $1bn to now more than $10bn with the share price rally -- has traded his way out of trouble. But the tycoon has, at the same time, abandoned an audacious, decades-long quest to build his own mobile phone network, leaving "bittersweet" feelings said one person close to him.

"It was not preordained that it was going to work out this way," said Craig Moffett, the longtime US telecoms analyst who has followed Ergen for years.

Ergen, who in his 20s had a stint as a professional poker player, founded EchoStar in Colorado with his wife and another partner in 1980, launching a single satellite. The industry would over the years be plagued by heavy spending, technological failures and multiple bankruptcies, with heavyweights such as General Motors, Rupert Murdoch, Motorola and AT&T at various points getting in and then abandoning the business of launching rockets into space.

Ergen would go on to launch the Dish Network, a pay-TV satellite company that he would eventually split off from EchoStar. Ergen developed a reputation for parsimony and stubbornness, never paying more than what he thought was a fair price for anything. Sometimes that meant picking fights with broadcasters such as Disney over the cost of distributing sports channels or -- as the Financial Times reported in a 2013 profile -- telling staff they could not be reimbursed for tips over 17 per cent in restaurants when travelling.

But by the end of 2023, Ergen had ceded much of his favourite asset: control. EchoStar and Dish had remerged but had a combined debt balance that exceeded $20bn. The group also had $4bn of maturities approaching in 2024 and 2025 that could not be easily refinanced. But the junk bonds, while complex, was underwritten with varying collateral and enough flexibility to allow Ergen to reshuffle the pieces to exert pressure on bondholders.

In January 2024, Ergen launched a so-called distressed exchange offer where bondholders -- who included Silver Point Capital, Apollo, and the insurer, Prudential -- were asked to take as little as 55 cents on the dollar for their paper, with the threat that those not playing ball would see their collateral pushed out of their reach.

Even in a rough-and-tumble world of distressed debt, participants were taken aback by Ergen's militancy. Over the spring and summer, talks between the sides took place with creditors insisting that Ergen himself join the sessions, either in Colorado or at the Manhattan office of Echostar's longtime outside counsel, White & Case.

By the end of September 2024, cooler heads had largely prevailed. The sides agreed that bondholders would take narrower haircuts than Ergen's original offer, and billions of fresh capital would be raised.

Relations weren't exactly harmonious: a merger between satellite TV rivals Dish and DirecTV was scotched after Dish bondholders refused to take a $1.6bn discount on more than $10bn of debt, believing that value would simply be transferred to Ergen and TPG, the private equity backer of DirecTV. The company still carried more than $20bn of debt with other large maturities left looming.

Still, the debt restructuring and capital raise left Ergen with more breathing room to refocus on his long-term dream of creating a viable national cell phone network using the $40bn in spectrum rights EchoStar had accumulated. By January, however, there was a new president and another, much bigger problem.

In 2019, the first Trump administration waved through the merger of T-Mobile and Sprint, the US's third- and fourth-largest mobile operators. But as a condition of the deal, regulators forced T-Mobile to shed its challenger brand, Boost, to EchoStar. Ergen had been gathering spectrum for years and Boost was supposed to be his big break in pushing into the top tier of wireless providers.

Instead, by this year, Boost had only attracted a few million customers. Sector rivals accused it of "squatting", or hanging on spectrum with no real plan to deploy it.

Brendan Carr, the new chair of the US Federal Communications Commission, then sent a letter to Ergen in early May: "I have directed agency staff to begin a review of EchoStar's compliance with its federal obligations to provide 5G service throughout the United States per the terms of its federal spectrum licenses."

Elon Musk's SpaceX had long been a critic of Echostar's use of spectrum and had sent its own letter to the FCC in April, writing "Dish barely uses the spectrum" after years of "false promises and dubious technical showings".

EchoStar fired back in its own correspondence but the danger was clear. At the time, Musk was close to Trump and the worst-case scenario -- the government seizing back the spectrum -- was on the table. Ergen then made three fateful choices.

First, to deal with the financial risk, he "graced" three different company bond issues over the summer, skipping interest payments and putting them into a grace period. Second, he had an emergency bankruptcy petition readied in case Trump moved, believing a Chapter 11 process could temporarily halt any Trump aggression.

Finally -- encouraged by Chris Ruddy, founder of the conservative cable network Newsmax, which Dish Network had carried for several years -- Ergen decided to go and see Trump himself at the White House.

In the June Oval Office meeting, Ergen explained that EchoStar was a family business, like the Trump Organization, which employed thousands of Americans and that, with some patience from the Administration, the company could find a solution that pleased all sides, according to one person familiar with the meeting.

In late August, EchoStar announced it would sell $23bn of spectrum to AT&T, with the telco allowing Boost to operate on its network. EchoStar shares jumped 70 per cent. On September 8 came the SpaceX announcement, sending EchoStar shares soaring again.

Among the big winners on Wall Street are several distressed debt hedge funds that have each made hundreds of millions of dollars in paper profits. The likes of Darsana, Redwood and Silver Point Capital rank among EchoStar's top 10 shareholders and also have big chunks of an EchoStar convertible bond that can be swapped into equity at a sharp discount to the current price.

One debt fund told the FT that EchoStar was more intriguing than ever with spectrum worth perhaps $10bn to $20bn still left to sell, $42bn of cash coming in to repay debt and the merger between Dish Network and DirecTV expected to resurface at some point, given its logic.

But EchoStar -- with $8.5bn of SpaceX's private shares -- is also a public proxy for the mega unicorn, now valued at over $400bn.

Given the share price moves, an outstanding lawsuit that bondholders filed in 2024 against EchoStar accusing Ergen of improperly stripping their collateral is likely to be withdrawn or settled.

But Ergen -- who on Monday made a rare public appearance at a conference in Paris -- was not exactly jubilant.

He shared his optimism about his mobile phone ambitions, given the partnerships with AT&T and SpaceX that accompanied the spectrum sales. But he wistfully insisted that a standalone EchoStar would have created more value for shareholders in the long term, acknowledging that the Trump administration forced him into the scenario he had tried to avoid.

"When you play blackjack, you play the odds, and every hand, there's a right [or] wrong answer . . . that wasn't so dissimilar here, where the hand that we're dealt by the FCC was one that there's only one logical path that we're going to be able to take."

How telecoms tycoon Charlie Ergen wrestled debt-laden EchoStar back from the brink