Sir Alex Ferguson openly admits that his decision to sign Owen Hargreaves in the summer of 2007, was the most disappointing of his legendary Manchester United career.
The England midfielder arrived off the back of an impressive World Cup campaign 12 months earlier and a reputation enhanced thanks to his time at Bayern Munich. But chronic injury issues meant he never truly established himself at Old Trafford, leading to Ferguson’s non-too-flattering verdict on his transfer.
But there are similar regrets about a player signed in the same week as the combative midfielder. Anderson arrived in English football with the tag of one of Brazil’s most exciting talents.
Just two years previous, the central midfielder had been crowned the player of the tournament in the under-17 World Cup. At just 18, he was already involved in the senior Brazil side and was expected to be a key part of the Selecao’s plans moving forward.
United stumped up £27million to sign Anderson from FC Porto, fending off Real Madrid and Chelsea in the process. But despite winning four Premier League titles and a Champions League crown, he never really delivered on his promise.
And when his career ended prematurely aged just 31, it culminated as a major ‘what if’ not only for Anderson, but for Manchester United as a whole. Ferguson didn’t get too much wrong in the transfer market and those at the club think he would have got it spot on with Anderson - if only his attitude had been right.
"He could have been the best player in the world at one point, I promise you he could have," ex-United keeper Ben Foster told the UTD Podcast last year. "Everybody would say that he could have been the best in the world at one point.
"But he just didn't care, he didn't care about anything. Honestly, he didn't care about anything [laughs]. But you put him on a pitch and he was like that. Carlos Tevez was the same sort of thing. Put him on the pitch and oh my god. There has got to be something in being South American, there's got to be something in that."
That was a verdict which quickly bled into the coaching staff, with Ferguson’s trusted confidante Mick Clegg admitting that anger towards the talented South American even made its way to the boss himself.
“Anderson was one. You could never find a nicer person, he was popular with everyone but he was a lazy bleeder,” Clegg told the Athletic. “He always had his excuses. I used to have a stick and I said to Alex Ferguson very early on, if he carries on, I'm going to hit him with my bleeding stick.
“Fergie couldn't believe it. 'Don't you dare. He cost me a lot of money. You can't be hitting one of my players, are you mad?'
“Then, six weeks later, Fergie came to find me. 'Where's that bloody stick? Give me that stick. I want to hit him'.”
Clegg added that Anderson could have been “an absolute stormer of a player” but rather than apply himself properly, he decided to not put in the world and became a “party animal."
He would leave United 2015 after making almost 200 appearances for the club. He then had a short spell in Brazil, before returning to Europe to play in Turkey. However, that adventure was only a fleeting one and he hung up his boots in September 2020, with a boatload of regrets riding off into the sunset with him.