For one of Brazil's – and indeed the world's – most famous, most fervently supported football institutions, the lack of continental titles is a constant bugbear for Flamengo.
The Rio de Janeiro giants boast just a single Copa Libertadores title, clinched in 1981 with the brilliant Zico pulling all the strings. That same side went on to thrash Bill Paisley's Liverpool 3-0 to take the Intercontinental Cup the same year in one of the most comprehensive victories ever inflicted by a South American side on their European peers.
Since then, however, and despite repeated, sustained success at state and national level, Flamengo have been chronic under-achievers when it comes to the Libertadores.
But there is renewed hope that 2019 might prove to be their year, as an all-star side inspired by the unstoppable Gabriel Barbosa look to follow in Zico's footsteps and take the continent's biggest prize.
Barbosa's more familiar epithet, Gabigol, had taken on a sadly ironic meaning prior to his return to Brazil in 2018. Having been billed as Neymar's successor upon leaving Santos for Inter, the forward quickly discovered that he was out of his depth in Serie A, barely featuring for the Nerazzurri in his debut season before being shipped out for an equally underwhelming loan spell with Benfica.
Less than two years after moving to Italy to such fanfare, the young forward found himself right back where he started, desperate to regain form and, perhaps most important, confidence at Santos. He responded with a strong 2018 season that saw him net 27 goals in all competitions and 18 in Brazil's Serie A, a haul that earned him the division's top scorer crown.
That spectacular record may not have convinced Inter to bring their loanee back to San Siro, but it did grab the attention of one of Santos' rivals.
Flamengo swooped to seal their own loan move for the striker, still just 22, part of an ambitious recruitment plan designed to make the side competitive both at home and abroad.
Alexandre Vidal/CR Flamengo
Alexandre Vidal / Flamengo
As well as Gabigol, Flamengo moved for Olympic Games gold medallist defender Rodrigo Caio, Uruguay playmaker Giorgian De Arrascaeta and ex-Santos striker Bruno Henrique as they strengthened across the field.
This summer has also seen a flurry of activity, with two established European stars in Filipe Luis and former Bayern defender Rafinha joining the club. So far, results have not disappointed: after waltzing to the Rio State title, Flamengo currently lie second in Serie A and have progressed to the Libertadores last eight, where fellow Brazilians Internacional lie in wait on Wednesday.
Without Gabi's goals, though, it is doubtful the team coached by long-time Benfica boss Jorge Jesus would have got nearly as far. The striker is netting at a rate of a goal a game in Serie A, 11 in 11 appearances, and scored both his team's efforts to come back from 2-0 down to Emelec in the Copa last 16 before finally prevailing on penalties.
But while the likes of Monaco and Sevilla have been linked with his services in the current transfer window, Barbosa seems intent on glory at the Maracana.
“Our fans don't just want the Libertadores, they want the whole world!” he joked in an interview with Globoesporte this week.
“They are demanding. But Flamengo have been fighting for everything these past years and that is how it should be.”
The Maracana, that famous old stadium which is a living symbol of Carioca and Brazilian football, will be packed once more on Wednesday to take in Flamengo's first leg.
A strong result in front of their own fans will be key for the local heroes, particularly against an Internacional side who, unlike their rivals, have enjoyed recent successes in the Libertadores, having won the competition in 2006 and 2010.
Barbosa will sit out the clash, having suffered a muscular injury while scoring in the weekend's 4-1 derby rout of Vasco. His club will nevertheless be confident of getting the result without their top striker, who is hoping to regain full fitness in time for next Wednesday's decisive second leg in Porto Alegre.
The prize for the victor will be another all-Brazil tie in the semis, against either Gremio or Palmeiras. But Gabigol and his team-mates will be happy to take the competition one game at a time, blocking out the pain and frustration of 38 years without touching South America's biggest club trophy.
Only once this adventure has come to an end may he possibly turn his mind to what comes next for the Inter-owned attacker.
Certainly, he should have no shortage of admirers in Europe when it comes to deciding the latest move in a career that has already provided plenty of twists and turns.