The Italian international made an instant impact at La Bombonera.
Osvaldo was a favourite of Pochettino's at Espanyol. The Argentine boss moved fast to snap him up for a club record fee of £15 million, according to the BBC, when he became unsettled at former club AS Roma.
Six months later and he left the The Saints after a dismal time on the South Coast.
Osvaldo struggled for form, despite some flashes of excellence, before he found himself suspended for his part in a sideline brawl v Newcastle United.
Then he got in a fight with Southampton stalwart Jose Fonte in training and was suspended for two weeks by the club and expected to leave.
That he did. He joined Juventus on loan until the end of the season. And he was very happy to make the move - as he clearly never settled into English football and it did not look like he would be coming back.
He didn't. Instead Southampton did a loan swap with Inter Milan, Saphir Taider coming in the opposite direction. Of course, Taider's time at Southampton lasted even less than Osvaldo's.
He again got into trouble during his time at Inter and they cancelled his deal early this month. Osvaldo therefore decided to turn his back on Europe and head to his beloved Boca Juniors. The Argentine born striker signed a loan deal at the club this month.
Yesterday he made his debut for the team and, in typical Osvaldo style, was the centre of attention as he scored the winning goal in a Copa Libertadores tie with Montevideo Wanderers. His goal in the 43rd minute proved to be enough for a 2-1 win at La Bombonera as Boca won their seventh game in a row.