Flamengo are one game away from another Copa Libertadores final. After a goalless first leg in La Plata, their semi-final against Estudiantes will be settled at a sold-out Maracanã on Thursday night, with the final set for Montevideo on November 28.

Domestically, the 'Scarlet and Black' are top of the Brasileirão, one point clear of Palmeiras with seven games left – including a potentially title-deciding trip to Abel Ferreira’s side on November 22.

It is familiar territory for the club's highly-regarded sporting director José Boto. The former Benfica chief scout, who also worked at Shakhtar Donetsk, PAOK and NK Osijek, arrived at the end of 2024 as one of president Luiz Eduardo Baptista’s first appointments – and in his first season, Flamengo won four trophies, including the Libertadores and the Brazilian title.

Chasing Back-to-Back Doubles

Flamengo are seeking a repeat of 2025, but Boto is not getting carried away just yet.

“We hope to have a season like the last,” he told GIVEMESPORT at last month’s Portugal Football Summit in Lisbon. “Now we are in the semi-finals of the Libertadores, and we are ahead in the league. But there are no easy games in South America.”

That is an understatement. No club has won the Libertadores and the Brazilian title in back-to-back years since Pelé’s Santos in 1962 and 1963.

“We hope to do that and, for me, it would be very gratifying because it’s only my second year at the club,” said Boto, who has already overseen one change of head coach, with Leonardo Jardim replacing Filipe Luís in March. “If I achieve this, and with two different coaches, it will be a positive sign that the work we are doing here is paying off.”

Flamengo Fans Want Stars

Spending power has never been Flamengo’s problem. They are one of the richest and most successful clubs in Brazil. However, satisfying their fans' appetite for star names is another matter. And it's not always easy to compete for targets against European rivals for signings.

“Flamengo, and I think many other clubs in Brazil, operates in a unique market," said Boto, who was linked with a move to Milan over the summer having worked with Ruben Amorim at Benfica. "The fans like to have star names, regardless of how they perform. They just want names.

"At Flamengo, we have to consider this when recruiting. And, most importantly, we have to win every year, because this is also what the fans demand, along with everyone else [at the club]. Of course, we have the money for that.

“We try to bring in experienced players who have played in Europe, and then mix that with some younger signings. During my first three windows, we focused on well-known signings with careers in Europe, like Jorginho, who played for Arsenal, Chelsea and Napoli. And we signed Danilo, Alex Sandro and Saul. They each bring quality, adding both technical skills and exactly the type of mentality we are looking for."

That policy has already paid off. Danilo, who signed from Juventus in 2025, scored the only goal of last year’s Libertadores final against Palmeiras in Lima.

This summer, however, Flamengo changed tack.

“In the last window, because we already have a very experienced group, we made some signings for the future – younger players,” said Boto. “We brought Ecuador international Anthony Valencia from Royal Antwerp, and signed a very young prospect from River Plate, Joaquin Freitas, who I think, in the next few years, will be the new Lautaro Martínez. He has already been capped by Argentina. We didn’t need more experienced players in this last window, so we decided to make some bets on the future instead.”

Signing South American talent is one thing. Keeping hold of Brazil’s own brightest stars is an entirely different challenge. Estêvão left Palmeiras for Chelsea in 2025, a year after Endrick swapped the same club for Real Madrid.

Boto accepts that even Flamengo cannot stop the exodus of some of the club's most promising Brazilian prospects. During his time with Flamengo, Wesley joined Roma for €30m, and Ryan Roberto moved to Shakhtar Donetsk, Boto's former club, for €10m. And the club's record sale remains Vinícius Júnior, who left Flamengo for Real Madrid when he turned 18 in July 2018, for €45m.

“It is very difficult to keep these kinds of players because it’s the dream of all Brazilian kids to play in Europe,” admitted Boto. “Even Flamengo or Palmeiras, who are in a strong financial position, face this problem. In many cases, the players don’t want to stay. They want to jump to Europe, and we have to understand that. It’s almost an obligation to sell players so young [to Europe], and we don’t keep this talent in Brazil.

“It’s a pity, because sometimes these players are not ready to play in Europe. If you look at Estêvão at Chelsea, or Endrick at Real Madrid, they are not ready for that level yet. If they stayed one or two more years in Brazil, they would arrive in Europe and be able to put in consistent performances. But that’s just the market. Nobody wants to wait, and it’s impossible to keep that talent in Brazil.”

Inside Paqueta's Flamengo Return

Another example of this came when when Lucas Paquetáleft Flamengo in 2019 for Milan in a deal worth €35m.Six years later, Boto was able to bring the Brazil international back to his boyhood club in January in a deal worth €42m, a record fee for any South American club. It was a far from a routine negotiation given West Ham had originally asked for €60m, and wished to keep Paquetáuntil May as they strived to avoid relegation.

“Firstly, it was a very tough transfer to negotiate with West Ham. It was a negotiation lasting two months – and it was only possible because of the player’s wish to play for Flamengo,” said Boto. “If not, I have to tell you, it would have been impossible to reach that price. If the player had wanted to play for another Premier League team, or something like that, for sure we would not have made that deal.

“It was a very difficult deal with the owner of West Ham. Very, very tough. It was me who led the negotiation from Flamengo’s side. I’m very happy to have signed him. In my career as a sporting director, it was one of the hardest negotiations I have been involved in.”

Paquetá also arrived aged 28, younger than some of Flamengo’s other European imports such as Jorginho and Danilo, who are both in their mid-thirties.

“Firstly, he's still at peak age, and he also brings the passion to play for Flamengo," said Boto. "That’s very important, because sometimes it’s hard for us Europeans to understand how the people, and even the players, live and breathe for the clubs they love in Brazil.”

Flamengo A 'Top Six' Premier League Team

That passion was impossible to miss at last year’s Club World Cup. Flamengo’s supporters made up most of the 54,019 crowd in Philadelphia as they came from behind to beat Chelsea 3-1 in the group stage, before a 4-2 defeat by Bayern Munich in the last 16.“For us, the Club World Cup was important, not only on the financial side where we brought in good revenue, but it was also a possibility to see how we compared with European clubs,” said Boto. “We beat Chelsea, and they won the tournament. We lost against Bayern Munich, but it was a fantastic game. So we are on the right path, and if we competed in Europe, I believe we could match with these kinds of clubs.

“For Brazilian football fans, this possibility to compete with European clubs is important. A question they always ask is, 'If Flamengo was in the Premier League, which position would they be? Where would Flamengo finish?'

“I think in the first five or six. We have that conviction. Of course, we know the rhythm and pace is faster in the Premier League than in Brazil. But last year we played 78 games. If the fixtures were reduced, we could compete at the pace the Premier League teams play with. This is my feeling, of course, without any scientific evidence.”

That fixture pile-up is why Boto would welcome Brazil following Major League Soccer, which will switch to a European-style calendar running from July to May starting from 2027.

“I think it would help the competition,” he said. “The problem in Brazil is that we have a lot of competitions in Brazil that are all important. For instance, we have the Estadual, where all the teams of Rio compete to see who is the champion of the State. It's the same with all the teams from São Paulo. These games are very valuable to the local associations, and that’s why we start in January.

"We play this tournament until almost March, and then the league and the Libertadores start. That’s why we arrive at the end of the season with more than 70 games. For me, as a sporting director, I prefer to have a calendar like Europe. But I think it will be impossible to do that in Brazil.”

The Brazilian Football Confederation (CBF) has already capped the state championships at 11 dates and brought the Brasileirão’s start forward to 28 January this season, but the two still overlap – the Carioca final, to crown the Rio champion, was not played until 8 March. Flamengo beat Fluminense to win their 40th title.

Filipe Luís Destined For The Premier League

Boto also had to navigate a manager change this season, as popular former coach Filipe Luis departed in March. He was sacked just hours after an 8-0 win over Madureira had sent Flamengo into the Carioca final. Defeats to Corinthians in Brazil’s equivalent of the Community Shield, and to Argentine side Lanús in the Recopa Sudamericana, had added pressure prior to the decision being made.

Leonardo Jardim, who won Ligue 1 with Monaco in 2017, replaced him, and, four months later, Luís took charge at Monaco on a deal until 2028. In January, Luis was also linked with a move to his former club Chelsea, but the Blues opted for Liam Rosenior to replace Enzo Maresca instead. Boto is confident Luis will move to a Premier League club one day.

“Filipe was in his first year as a professional coach with us, and he won everything," said Boto. "I think nobody in the world has done that. He is very ambitious, and his mission was always to coach in Europe. He’s now at Monaco and is doing well, and he is someone who, in the next – I would say five years maximum – will be at a top, top club in the Premier League.

Monaco led Ligue 1 at October’s international break, having made their best start since 1991/92, before a first league defeat at Lorient on Sunday dropped them to fifth, but still level on 14 points with leaders Lyon.

“He is very good," added Boto. "He is well-prepared and ambitious. He has now taken the right step – not to go to a big, big club, but to a medium-sized club like Monaco, which allows him to get to know European football without so much pressure. But he is good enough to arrive at a top club in the big European leagues, like England, Italy or Spain.”

​​​​​​​De Zerbi Can Turn Spurs' Fortunes Around

Boto is also keeping one eye on how his former club, Shakhtar, fare in the Champions League. The Ukrainian side are playing their 'home' games at Stamford Bridge and have fixtures there to look forward to against Sporting CP, Fenerbache and Real Madrid as they look to get out of the league phase.

Boto spent three-and-a-half-years at Shakhtar, joining as head of scouting in July 2018 and leaving for PAOK in December 2021. In that time, Shakhtar won two Ukrainian league titles, the Ukrainian Cup and the Ukrainian Super Cup – the last of them under the now Spurs boss Roberto De Zerbi.

De Zerbi kept Spurs up on the final day of last season, but a club-record summer outlay of more than £300m, including up to £100m on Sandro Tonali, was followed by their worst ever Premier League start after six games. Their first league win only came on Monday against Coventry. Boto is backing De Zerbi to get improved results, and believes Spurs loanee Mykhailo Mudryk can also have an impact in north London when he returns from injury.

“I like Roberto De Zerbi a lot. He’s different from all the other coaches,” said Boto. “He has a special football brain, and sometimes it’s difficult to understand what he wants. It takes time.

“I’m surprised by Tottenham's start [to the season]. I was hoping for more. I think everyone was thinking the team would perform better. But if he gets time – which in football is something that is very precious – he will make Tottenham play better and get results.”

Mudryk’s reunion with De Zerbi hasn't really got going yet. Cleared to play in July after his four-year ban for meldonium was reduced, he joined Spurs on loan from Chelsea on deadline day, only to suffer what De Zerbi called a “stupid” ankle injury in training. Spurs hope the Ukrainian winger is back before the November international break.

“Look, I had Mudryk at Shakhtar for some years," said Boto. "He has a lot of natural talent, and he's a special kid who lived through some difficulties when he was a child. He needs to have someone who takes care of him. I think Roberto was the first one who treated him like his son.

“He has incredible talent. He has everything a top player needs: speed, pace, technique and vision. He needs to concentrate everything on football – we know it’s not easy. A kid who comes from Shakhtar Donetsk to Chelsea for big money, that is a weight on his back. But I think if he solves all his problems off the pitch, he will be one of the most exciting talents the Premier League has.”

By the time Mudryk is back on the pitch, Boto’s own season will be nearing its climax. Estudiantes arrive at a sold-out Maracanã next, with Palmeiras, the side Flamengo beat in last year’s final, or Rio neighbours Fluminense, awaiting in Montevideo for the winners. The Brasileirão, meanwhile, runs until 2 December. Win both, and Boto’s second season will have matched his first – a feat no Brazilian club has managed in 63 years.