A European Cup winner with Benfica in 1962, a 10-time Portuguese champion and a member of Portugal's 1966 World Cup semi-finalists, Simões played alongside Eusébio during one of the greatest periods in the country's football history.
So when asked to compare Eusébio with Cristiano Ronaldo, he immediately pushes back against the idea that the two can simply be placed side by side.
“I will not compare Eusébio with Cristiano Ronaldo, or vice versa, because I think it is a mistake to compare them," Simões tells Football Presse.
“A lot of people have come to me and said, ‘If Eusébio played today, would he score more goals?’ I don't think that is a very intelligent question. I would ask the opposite question.
“And the opposite is this: if Cristiano Ronaldo had played in that time, could he have scored the same number of goals that Eusébio scored? That is the big question.
“I have a lot of doubts about that. I don't know if Cristiano Ronaldo could have scored the same number of goals that Eusébio did with those pitches, that grass, those boots, that ball and all the other conditions they had at that time.”
The question has acquired another layer since Simões gave the interview.
Ronaldo has continued to rewrite the Portuguese and international record books. By 2026, he had scored 146 goals in 233 appearances for Portugal, making him the men's international record-holder for both goals and appearances. He also became the first player to score at six different World Cups.
At the 2026 World Cup, he moved beyond Eusébio's World Cup scoring total, taking his tally to 10 goals and becoming Portugal's outright leading scorer in the competition. Eusébio had scored nine at the 1966 finals, winning the Golden Boot as Portugal finished third.
Yet those numbers do not change Simões' fundamental argument.
If anything, they make the question more interesting.
“I would love to see Cristiano Ronaldo playing in the same circumstances that Eusébio played in and scoring the same number of goals that Eusébio scored.
“If Cristiano Ronaldo was playing in that time and scored the same quantity of goals that Eusébio did, then I would have no questions. But I have a lot of doubts about that.
“I have a lot of doubts because we are talking about completely different circumstances. Today, players have everything to help them. The conditions are different, the equipment is different, the pitches are different and the ball is different.
“So I don't think it is fair to take the numbers and say, ‘This player scored more, so he was better.’ You have to look at what the player had around him and what he had to overcome.”
That is particularly relevant when discussing Eusébio because Simões was not simply a contemporary watching him from the stands.
He played with him.
He knew the player behind the numbers, and experienced first-hand the football in which Eusébio became Portugal's first global superstar.
Eusébio scored 41 goals in 64 appearances for Portugal, with nine of them coming at the 1966 World Cup. Four arrived in one of the tournament's great individual performances, when Portugal recovered from 3-0 down to beat North Korea 5-3 in the quarter-final.
Ronaldo's international career has subsequently taken the Portuguese record to a level that even Eusébio's generation could scarcely have imagined. He has also remained a central figure for Portugal deep into his career, playing at the 2026 World Cup at the age of 41 before confirming that it would be his final appearance at the tournament.
But Simões is not arguing that Ronaldo's achievements should be discounted. His point is that football history cannot always be reduced to a spreadsheet.
“You cannot know what would happen. Maybe Cristiano Ronaldo would score more goals, maybe Eusébio would score more goals, maybe they would both score less. We don't know.
“That is why I don't like these comparisons. They played in different generations, with different conditions and different football.
“What I would like is to see Cristiano Ronaldo playing with the same conditions Eusébio had. Give him the same grass, the same boots, the same ball, the same football of that time and then see what happens.
“Because Eusébio did what he did in those circumstances. That is why I have a lot of respect for what he achieved.”
And that is ultimately where Simões' argument rests.
Ronaldo's longevity, scoring record and extraordinary consistency have made him one of the defining players in football history. Eusébio's explosive peak, particularly at the 1966 World Cup, made him the symbol of an emerging Portuguese football power.
Both records tell part of the story.
For Simões, however, the more interesting question is what those records cannot tell us.
“If you want to compare them, you have to put them in the same situation. Otherwise, you are comparing things that cannot really be compared.
“I saw Eusébio. I played with Eusébio. I know what he did and I know the conditions in which he did it.
“I also know what Cristiano Ronaldo has done, and what he has achieved is incredible. But if you ask me whether I am certain he could have done what Eusébio did in that time, I have a lot of doubts.
“That is the question I would like to see answered.”