He had the football world at his feet. A midfield talent like few others, Oscar was already the star of a World Cup and a vital cog in not one, but two Premier League-winning campaigns.
At 25, the Brazilian seemed to have everything in place to cement his position in the game's elite.
However, in January 2017, he dropped a bombshell. The Chelsea man gave up on his dream of dominating European football and moved to China, signing a hugely lucrative four-year deal with Shanghai SIPG worth £20.8 million ($26.5m) a year that made him one of the world's highest-paid players.
Two years have now passed since that momentous £60m ($76.5m) transfer, and while predictions made at that time over how Chinese football was ready to compete with Europe's big leagues proved incorrect, Oscar has been a huge success in Shanghai.
Perhaps the most striking thing about this elegant, cultured playmaker is his knack of finding himself at the heart of winning teams.
From the Recopa Sudamericana in 2011 with Internacional to two Premier League crowns at Chelsea and international glory in the Confederations Cup and Under-20 World Cup – with a hat-trick in the 2011 final he achieved a feat only the great Geoff Hurst had previously managed – Oscar has an enviable collection of trophies.
Since moving to Shanghai he has carried on that tradition. Having finished runners-up in the Super League in 2017, Oscar's debut season, the side coached by Vitor Pereira went one better last year to take the title, the first in the club's history.
Oscar was predictably in the thick of things.
With 19 assists across the league season, he beat compatriots Renato Augusto and Hulk (his team-mate at SIPG) to the award for best provider. The 27-year-old added a further 12 goals of his own making, meaning that of SIPG's 77 Super League strikes, he was directly involved in no less than 31.
While attacking partner in crime and Chinese football legend Wu Lei was named Player of the Season thanks to his exceptional haul of 27 goals in just 29 games, Oscar nevertheless earned a place in the CSL's best XI.
Even with wages that set SIPG back around £400,000 ($510,000) a week, Oscar proved his worth. Of course, his pay packet remains a major talking point but he has been remarkably up front about his motivations for leaving Chelsea for relatively uncharted territories.
“Every football player, or every person who works, wants to earn money to help their families,” he explained back in 2017 to Copa 90.
“I came from a social background in Brazil that is very poor. We didn’t have anything. This is the fruit of my work and when I earn this, it is because I conquered it.
"The same way I came here, I will be able to return to Europe.”
His decision of course came at a cost. Previously an undisputed member of the Brazil team, Oscar last featured for his nation all the way back in November 2015.
Selecao coach Tite has shown himself willing to play China-based talent, with Renato Augusto and Paulinho both featuring in recent squads. However, Oscar has found no way through, his habitual spot blocked by Philippe Coutinho.
Consequently, he finds himself in an acute dilemma. He undoubtedly retains the ability to shine again at the very highest level, but with two years left on his contract at SIPG and astronomic salary commitments, he is not exactly an attractive financial proposition for Europe's elite.
For now, then, he will continue to prove that China is not a country where footballers go to die, with the AFC Champions League the big prize on offer in 2019, along with the challenge of retaining the Super League title.
The example of Paulinho also shows that one can return from the Far East, while the Copa America looms large on the horizon, with places still up for grabs in the Selecao squad for this year's tournament in his native Brazil.
Did Oscar err in following the yuan to a relative footballing backwater? Perhaps.
The midfielder, however, made what he believes was the correct decision not just for himself but for his entire family, having now set them up for life.
In addition, his exploits in China have shown that he remains a special talent, a valuable asset for any team.