And not over whether to cross or shoot or anything of such a routine nature for sportsmen.
Rather, it was of the sort that pretty much decides and defines careers.
Would De Rossi stay with the team that he was emotionally attached to and try and drive them to an unlikely but ultimately more “pure” success; or would he make the big-money move in which he was almost certain to win trophies but not necessarily be essential to them.
At 28 the midfielder had spent his entire career at Roma but only had two Coppa Italia medals to show for it. Worse, the club had finished second in Serie A in four of the previous six seasons and, with a hugely talented midfielder like De Rossi about to enter the peak of his career, had seemed to have blown their chance of ever winning a title any time soon.
So, as the January transfer window ticked down and he still hadn’t signed a new contract, De Rossi now also had an offer from Manchester City on the table. Roberto Mancini was even describing him as a “perfect fit” for the club.
Chelsea, Paris St Germain, Manchester United and a host of other top clubs had previously been interested.
And Mancini would prove part of the pack in another way: De Rossi would also eventually say no to him as well. The perfect fit for the midfielder, personally, remained Roma.
At the end of the window, he signed a five-year extension to the delight and relief of local fans.
“What drives me to stay here, to do my job with so much passion, is this team, this city and its people,” De Rossi proclaimed.
Of course, the midfielder’s loyalty to his home club has meant the football world at large has often been unaware of the world-class scale of his talents.
Those who watch him regularly, though, know his true value. Roma, after all, have made him the best-paid Italian player in the world — overtaking Gigi Buffon and his own club captain, Francesco Totti.
But De Rossi has already started to repay them.
After a slow start to this season as Roma adjusted to new manager Luis Enrique’s Barcelona-inspired approach, the team have recently hit form.
And central to all of that, in every sense, has been De Rossi.
As part of Enrique’s formation, the “future captain” — as Roma fans call him — has withdrawn to a deep-lying playmaker role, both breaking up opposition and initiating attacks.
Indeed, his importance was illustrated yesterday as Roma fell to a 4-1 defeat at Atalanta with De Rossi in the stands, reportedly disciplined for arriving late for training (occasional disciplinary problems are the one remaining flaw in his character).
Nevertheless, it was De Rossi’s passing ability from midfield that particularly caught Mancini’s eye given how City lack true ingenuity in midfield behind David Silva.
And it’s also that which may prove especially troublesome for Ireland in Poznan.
Against a side such as Italy, Giovanni Trapattoni is likely to get his rigid Irish team to sit very deep. In games like that, the more advanced attackers are often frustrated as space is congested around the box which is exactly where De Rossi’s initiative and incisive passing may well come in. With more space around the centre, he’s likely to be on the ball an awful lot. And well knows how to use it.
Along similar lines, he has illustrated an aptitude for delivering for Italy when arriving late. In the 2006 World Cup, after a four-game suspension for an elbow on USA’s Brian McBride, he came on as a sub in the final and smashed home one of Italy’s penalties in the winning shoot-out.
As the reigning world champions then underperformed under Roberto Donadoni at Euro 2008, it was De Rossi’s drive and goal against France which at least delivered them to the quarter-finals.
As with Roma, De Rossi is certain to be even more central for Italy this summer. And that may provide Trapattoni with his own dilemma.