By the time of the 2008 financial crisis, Juan Figer was in his mid-70s and winding down his career. By his own reckoning the first FIFA-authorized agent in Brazil had brokered more than 1,000 transfers in the four decades since he arrived from Uruguay as a young man. Dozens of the trades had been routed through his native country for the benefit of the shareholders of Panama-based Laminco Corporation International. The procedure had survived a parliamentary inquiry in his adopted home and was still operational, although on a smaller scale.

It was time for Figer to relax a little and reacquaint himself with his homeland, which he had left all those years ago. Now he would spend the summer months in the Uruguayan beach resort of Punta del Este while his sons Marcel and André oversaw business back in landlocked São Paulo. “I got used to the city but I miss the sea, now more than ever,” he told Brazilian newspaper O Globo. “I was born in Montevideo, near the water.”

But, while the transfer market veteran did not have the energy to jet around the world anymore and had closed his offices in Madrid and Tokyo, he could still pull off a big deal thanks to his contacts, including his old friend Jorge Nuno Pinto da Costa, who was also into his eighth decade.

Figer had known the FC Porto president for the best part of three decades. Their relationship dated back to 1986 when the agent represented Walter Casagrande, a 6-foot-3 striker who played for Brazilian club Corinthians. Casagrande, part of Brazil's 1986 World Cup squad, had fallen out with the club and Figer acquired control of his transfer rights. With his cut of this arrangement, the striker bought an apartment for himself and one for his parents on the outskirts of São Paulo. In a stopgap measure, Figer arranged for Pinto da Costa to take Casagrande on loan for six months at Porto. It was a surprise for the 23-year-old player because he wanted to follow his former Corinthians teammate Sócrates and play in Italy, then the most prestigious league in Europe.

As northern Portugal's winter closed in, Casagrande found himself alone, without his family, and miserable in a hotel. He would later admit in his authorized biography to experimenting with heroin in local bars during those dark days. By the summer he was off to Italy's Serie A to play for Ascoli after a $750,000 transfer and he and Figer were back in business.

Figer and Pinto da Costa had much to reminisce about from these days. They could also talk about FC Porto's 2-1 come-from-behind win against Bayern Munich in the 1987 European Cup final in Vienna. Rabah Madjer, an Algerian, scored the equalizer for Porto with an exquisite back heel in the 87th minute. Juary, a Brazilian forward, scored the winner three minutes later to seal Pinto da Costa's place in the folklore of his home city. Porto went on to win the Intercontinental Cup by beating Peñarol, the club Figer was still a fan of, even after almost 40 years of living in Brazil. “A man can change his wife, his political party but not his football team,” Figer said.

Neither of the two elderly men was ready to retire. In 2008, Figer arranged for Givanildo Vieira de Sousa – better known as Hulk because of his impressive physique – to move through Club Atlético Rentistas to FC Porto.

Hulk who, like other Figer clients, did not actually play in a match for Rentistas had been contracted to Tokyo Verdy in Japan until a few weeks earlier. The deal earned Panama-based Laminco as much as $19 million and was perhaps the most lucrative deal Figer had pulled off for the offshore company's shareholders, whoever they were.

The following year, two Englishmen left London's rain-swept autumn to go to the same resort where Figer spent the summer. They checked in to the Conrad Punta del Este Resort & Casino hotel, which billed itself as a Las Vegas-style betting oasis with 75 card-playing tables and 500 slot machines. Malcolm Caine, a man in his 60s with thinning white hair and a slight paunch, lived in a $2 million townhouse in a leafy north London cul-de-sac in St. John's Wood. He was a racehorse owner whose friends included Jonathan Barnett, one of the UK's most prominent football agents.

Barnett, who had begun his working life in his family's casino business, had built up his client base by agreeing to represent eight members of England's Under-16 team after approaching them and their parents after a match against Germany in the English town of Chesterfield in the early 1990s. He had begun to represent Gareth Bale as a 15-year-old, eventually negotiating his move to Real Madrid. Now the Stellar Group agency he had founded with David Manasseh represented some 200 footballers. Forbes magazine rated Barnett as the fourth highest-earning agent in sports, pulling in $44 million a year in commissions. That put him behind only Americans Scott Boras and Tom Condon, and Ronaldo's Portuguese agent Jorge Mendes according to the magazine.

Barnett would occasionally break from his hectic work schedule to go to the races with Caine and watch their horses in action. On a May evening in 2014, they saw their four-year-old gelding Café Society come first in a seven-horse field at Windsor, west of London, for its third victory in 18 months. A few days later, they sold the horse at an auction in London to a group of Australians for £330,000.

On the trip to South America, Caine's companion was a lawyer more than a decade his junior. Graham Shear held a 5% stake in Barnett and Manasseh's Stellar Group. Shear was familiar with the world of football finances. He had helped Michael Tabor, the British bookmaker turned racehorse owner, draw up more than a dozen loan agreements with Spanish and Premier League clubs through offshore companies. Over a month in late 2009, Caine and Shear met four or five of second-division Uruguayan club Deportivo Maldonado's directors at the casino hotel.

It was spring south of the equator and the resort was quiet before the start of the summer holidays, which coincided with Christmas and New Year in this part of the world. Most of the blinds were shut in the whitewashed condominiums overlooking the beach. Although fishermen were busy each morning on their scruffy tugboats, the harbour was not yet heaving with the pristine mega yachts that would arrive in a few weeks when South America's jet set arrived.

Three miles inland from the beach strip, Deportivo Maldonado's humble stadium was of a different social standing from the holiday destination that attracted the region's high rollers. The club's offices were in a small building with fading green paint. The team's emblem, an unhappy-looking whale spouting water, was also etched on the façade. The building looked more like a primary school than a football club's headquarters. A few rows of uncovered concrete terracing served as seating for the 200 or so fans that bothered to turn up for home games.

As part of his investment in the obscure club, the British racehorse owner planned to buy the transfer rights of players from across South America, typically those in their national Under-20 teams, before trading them to European clubs. It was a variation of the so-called ‘pases puente’ or bridge transfers that Juan Figer had been arranging through Uruguayan clubs since the 1980s. The difference was that Caine actually owned this team. He pledged to cover the expenses of Deportivo Maldonado's football operation. The average wage of a second-division player in Uruguay was as little as $600 a month at the time, meaning that the Englishman would have to cover an annual payroll cost of about $150,000. That was less than what Gareth Bale earned in a single week at Real Madrid.

The discussions, conducted politely in English, were productive and eight days before Christmas, contracts were signed. Caine registered a new company to control the football club. The formation of Deportivo Maldonado's holding company was made official in Montevideo.

Under Uruguayan law, the company had to have at least five directors. Caine became president and appointed his sons by his South African wife, David and Leon, as directors, along with two Uruguayan administrators. Shear became vice-president. There was no press conference or press release to mark the event. In fact, little seemed to change.

Caine's arrival was hardly noticed in this quiet backwater of South American football: Maldonado failed to win any of its first six games under its British owner, and finished the season ninth out of 13 second-division teams. But, it was making several moves in the transfer market. In one of his first deals, Caine signed Willian José da Silva, who had recently broken into Brazil's Under-20 team.

Willian José's story was typical of the rags-to-riches life of many Brazilian footballers. He was one of five children of a security guard and housewife from Porto Calvo in the northeast state of Alagoas. The small town is dominated by a whitewashed church – Our Lady of the Presentation – built by Portuguese settlers in the 17th century. The Portuguese had exported sugar and wood from the dense woodland around the town back to Europe.

The Da Silva family lived in one of the dozens of simple one-storey homes leading out to fields. As a 10-year-old child, Willian José used to earn pocket money by carting the shopping of locals at a Saturday street market to their homes in a wheelbarrow. But he preferred to take afternoon naps in the shade of the church and told his mother, Edileusa, that he was too shy for the work.

At age 12, he got into football, a relative latecomer in Brazil. He quickly made an impression for his poise and fierce shooting, and three years later was offered a contract by Gremio Barueri, 1,200 miles away in São Paulo.

He went to Brazil's biggest metropolis with his elder brother Washington as a chaperone. Just as the brothers arrived, the team began rising up through the divisions and was soon taking on Brazil's biggest clubs, thrusting the timid boy forward into the spotlight. He excelled, scoring 15 goals in one season, and was suddenly in demand.

By now, he had his own agent, Nick Arcuri, who advised him to sign for Deportivo Maldonado. Willian José said he did not go to Uruguay to register with the club, nor had he any intention of playing there. All the paperwork was done in São Paulo, he said. He was immediately loaned to the first-division team of the same name, São Paulo, where he became an understudy to national team striker Luis Fabiano.

He initially found it difficult to adapt to the pace and pressure of elite football. It was not until the following year in Santiago, during a game against Universidad de Chile, that he began to find some form. In an encounter that was live on national television, he volleyed a shot into the roof of the net. São Paulo went on to win the competition.

Caine, more at home in horse-racing circles than on the South American football scene, received assistance from Argentine player agent Gustavo Arribas, once a partner in the HAZ player agency with Israeli dealmaker Pini Zahavi. It was Arribas who arranged Willian José's contract with Deportivo Maldonado. He would also handle other negotiations with a growing number of up-and-coming players that the club acquired – such as Alex Sandro, a Brazilian defender, and two teammates in Paraguay's Under-20 squad, Marcelo Estigarribia and Iván Piris.

Without playing a game in Deportivo Maldonado's humble stadium, Alex Sandro moved to Porto for a €9.6 million transfer fee and the Paraguayans fetched €1.2 million in fees when they moved on loan to Juventus and AS Roma. Typically, players involved in such deals through Uruguay would get 15% of the transfer fee under the arrangements – something that FIFA allowed, even if it was not in their regulations.

Caine told us by email that his interest in acquiring Deportivo Maldonado was in order to develop players. He said that Uruguay had produced some of the world's finest footballers, mentioning striker Luis Suárez who had gone on to play for Ajax, Liverpool and Barcelona. The club operated exactly like any other team, Caine said, and met all tax and other statutory requirements. “Our investment includes infrastructure, managerial, technical know-how, medical and other facilities as well as player development, training and players transfers,” Caine wrote.

According to the club's chairman Federico Alvira, who handled the day-to-day running of the club, foreign investors were attracted to Uruguay by its tax regime. With little or no capital gains tax, it was a centre for offshore banking and known as the “Switzerland of South America”. Lionel Messi, the four-time world player of the year, had recently set up a company in Uruguay to route income from his endorsement contracts. It was a legitimate arrangement, but Messi ran foul of the Spanish tax authorities for not declaring the revenue in the country where he lived.

Officials at the Uruguayan football federation were complimentary about Caine's buyout, even though some of the players Deportivo Maldonado signed never actually played for the club. Fernando Sobral, the federation treasurer, said that Caine was providing much-needed revenue for the club and praised the efficient way the club was run.

While Deportivo Maldonado's players were always paid on time, other club owners in the Uruguayan second division consistently paid players late or not at all. In some cases those footballers were in a situation that “bordered on indignity,” according to the local player union boss. Many had to take a second job to provide for their families. They did not have medical insurance and their clubs did not have a doctor or physiotherapist if they got injured. They would have to travel to the union's headquarters for treatment.

In a late-night meeting, we spoke to a Uruguayan federation official in Zurich as he scoffed a plate of food on the terrace of the Renaissance Hotel on the eve of a FIFA meeting in 2015. “I don't see any problem with bridge transfers,” he said. He was irked that some football executives in Europe disapproved of them. “The financial gulf between here and South America is so big and these operations are helping some of our clubs stay in business,” he said.

In Brazil, the transfer of players like Willian José through Deportivo Maldonado barely raised a stir: moving young footballers through Uruguayan clubs had gone on since the 1980s and was regarded as standard procedure by sports reporters who covered player trading. “There's nothing secret going on here, nothing strange,” club chairman Alvira said.

Despite flashes of brilliance, Willian José was struggling to become a consistent goal-scorer even if he was racking up more loan fees for Deportivo Maldonado. The website transfermarkt.com estimated that the club received $2 million from São Paulo and $3 million from two other first-division clubs, Gremio and Santos.

Willian was getting restless from being shifted around clubs without, he said, being given time to find his form and show what he could do. But then, in January 2014, it looked like he might have made a breakthrough. While relaxing on holiday back home in flip-flops, shorts and vest, his agent phoned from São Paulo to tell him he was on his way on loan to Real Madrid – or at least its second team Castilla. The move would allow Willian to mix with Cristiano Ronaldo and Gareth Bale.

It is a formidable transition from a holiday in the lazy days of Brazil's midsummer to the European winters when players are at peak fitness. Adapting to a different time zone and a new language, it was dizzying for Willian José. “The first time I went into the dressing room my head was spinning because everyone was speaking fast,” he said.

Even so, after pulling on Real Madrid's white shirt for the first time for a match, he scored three goals in a 3-2 win in a ‘B’ team game at Recreativo Huelva in March. With Real Madrid's first team struggling in the league and Cristiano Ronaldo injured, coach Carlo Ancelotti promoted Willian to the first-team squad. He earned a place on the substitutes bench for a match at Celta de Vigo. But, wearing the No. 39 jersey, he got barely 20 minutes on the field in a 2-0 defeat and didn't get another chance during the rest of the season. His loan was not extended.

On a warm autumn evening on the outskirts of Madrid in October 2014, Willian was out on loan at yet another team, Real Zaragoza. It was his fifth stint on loan in as many years – a foil to the team's main striker in a match against Alcorcón. He held up the ball before laying it off for his teammate Borja “Baston” González, who scored twice in the 3-1 victory over the home team to maintain a promotion push. Willian and his teammates ran to one side of the cramped ground, to a few hundred Zaragoza fans in one corner. Like his companions, the Brazilian took off his jersey and handed it to one of the supporters.

A few days later, dressed in a grey cotton tracksuit and black baseball cap, Willian José was sprawled on a chair after training at Zaragoza's out-of-town grounds. He told us he was not happy with the way his career was going. Repeated loan moves had not given him time to settle down anywhere. He had not met Caine before but had complained to his agent, who had asked him to be patient.

At about the same time, Deportivo Maldonado turned its focus to two rising stars in Argentina. The club with 200 or so spectators at matches signed Gerónimo Rulli, a goalkeeper with Estudiantes de la Plata for a reported $4 million in 2014 and acquired Jonathan Calleri from Boca Juniors for as much as $12 million in 2016.

At 20 years old, Rulli had set a club record at the first-division team by going six games without conceding a goal. He told us that he travelled to Uruguay to sign a contract with Deportivo Maldonado, even if he didn't intend to play a game there. He was almost immediately loaned to Real Sociedad.

The 6-foot-2 goalkeeper won glowing praise from the Basque club's Scottish coach David Moyes for his debut season in La Liga. Moyes had been jettisoned by Manchester United and was trying to find his feet again in the north of Spain. In one match Rulli got the better of Gareth Bale when, in a one-on-one encounter with the winger, he blocked his shot.

Real Sociedad's board got rid of Moyes after just 12 months, but directors were determined to keep the young goalkeeper and signed him on loan for another year before making a move to sign him permanently the next year. Just as Real Sociedad officials were negotiating to pay some $8 million to Deportivo Maldonado for Rulli in the summer of 2016, Sheikh Mansour bin Zayed Al Nahyan's Manchester City stepped up and agreed to sign the young goalkeeper, according to the Spanish club's vice-president Angel Oyarzun. Then things got fuzzy. For some reason – one Basque newspaper even suggested it was uncertainty over the UK's decision to exit the European Union – Manchester City changed its mind about the deal. The club made no official comment, but Real Sociedad said it had agreed to immediately take Rulli back on loan from City and sign him on a permanent deal at the end of the year. City would maintain the right to buy him back in each of the next three summers, until he reached the age of 27.

On the southernmost tip of Spanish territory off the coast of Africa, Willian José had been making another new start at Las Palmas in the Canary Islands. It was his sixth loan move in as many years. The club had just been promoted to La Liga and wanted some firepower for its new campaign. The subtropical islands are the nearest point between Europe and Brazil and the climate, friendly locals and pace of life in Las Palmas were closer to his homeland than his previous placings in Madrid and Zaragoza. “I feel comfortable here,” he said.

By scoring nine goals, many of them match-winning scores, the globetrotting Brazilian helped the team earn a respectable mid-table place in La Liga. According to website transfermarkt.com, his laggard market value had finally risen, doubling to €3 million in a single season. A few weeks later, he was on his way to Real Sociedad for a fee of as much as €6 million.

In the same week, according to The Guardian, Jonathan Barnett negotiated with West Ham for Calleri to join the London club on loan from Deportivo Maldonado.

Caine himself rarely travelled to Deportivo Maldonado's modest stadium for matches. The club remained in the second division, finishing third a couple of times but not doing enough to gain promotion. According to official documents released by European clubs and estimates by transfermarkt.com, the Uruguayan team earned about $40 million in transfer fees for half a dozen footballers who hadn't played a match there. When we exchanged emails in 2014, Caine said that he had not yet made a profit on his investment. By then, the transactions, while complying with football regulations, had started to attract the attention of a FIFA official in Zurich.