Giuseppe Marotta missed out on signing Erling Haaland when the superstar striker was valued at a snip of his current value, while the Inter chief cannot see Paul Pogba ever returning to Serie A.
Now at Borussia Dortmund, Norway international Haaland is rated in the top bracket of the world's most lethal finishers, and he has been linked with the biggest clubs in Europe.
Marotta, Inter's chief executive for sport, has disclosed that during his time in a similar role at Juventus, there was an opportunity to snap up Haaland for what now would look like a bargain fee.
Speaking at the Festival dello Sport, Marotta said: "A big miss in my career? I say Haaland. When I was at Juve, I could get him for about S2-2.9million.
"But at the time we didn't have the strength to go extra-budget. Now he is among the best in Europe."
Marotta was with Juventus from 2010 to 2018, and the opportunity to sign Haaland is likely to have come in the closing months of his career in Turin.
It was announced in August 2018 that Haaland would leave Norwegian club Molde to sign for Salzburg, since when the 21-year-old has gone from strength to strength.
He has hit 47 goals in 48 Bundesliga games for Dortmund since making his debut for the German club in January 2020. Only Bayern Munich star Robert Lewandowski has netted more.
Haaland has outperformed his expected goals (xG) value of 37.36 by some way, while also contributing 11 league assists for BVB. On average, he has scored at a rate of 1.08 goals per 90 minutes played in the Bundesliga.
Marotta held his Juve role at the time of the club bringing in Pogba from Manchester United. Although the French midfielder later returned to Old Trafford, he has been repeatedly linked again with Juve while in England.
A return to Serie A for Pogba seems implausible, however.
"Will we see Pogba in Italy again? I think it is difficult, he still earns a lot in terms of salary," said Marotta. "At the moment there are no clubs capable of signing him."
Marotta's priority is ensuring Inter build on last season's Scudetto win, and to that end they look like keeping Lautaro Martinez for the long term.
Contract talks look like bringing about the outcome Inter have wanted, with the Argentine forward considered a key figure for the team's future.
"We will do everything so that he can continue at Inter," Marotta said. "With this renewal we are laying the foundations for the future with him at Inter, by making the right mix between young players and more experienced players."
Marotta explained at one stage how Inter had Juve forward Paulo Dybala in mind as a reinforcement, as they considered sending Mauro Icardi in the opposite direction.
Icardi ultimately became a Paris Saint-Germain player and Dybala stayed at Juve.
"There was uncertainty about Dybala's future," Marotta said. "Now, however, I think he will sign the renewal with Juventus, but there was the possibility of bringing him to Inter when we talked to Juve about Icardi."