You wouldn't expect a man who won two Champions Leagues, four domestic titles, one World Club Cup and one international World Cup to have too many regrets when looking back on his career.
Filippo Inzaghi was a cornerstone of Italian's dominant generation in the late 1990s-2000s and can have little to complain about in regards to a lack of silverware gathered across his career spanning 21 years.
So it isn't much of a surprise to learn the biggest regret of his career is something a bit more peculiar than most.
Of course, Inzaghi enjoyed most of his success with Serie A giants AC Milan - a key club in the career of a certain Zlatan Ibrahimovic.
After falling out of favour at Barcelona in 2010, the Swede's next move would prove critical in deciding how the rest of his career would pan out.
It turns out Ibrahimovic made a wise choice in Milan and hasn't looked back ever since.
The 34-year-old's second spell in Italian football may have only lasted two seasons but it was long enough for Ibrahimovic to make a very big impression on Inzaghi.
The Milan legend was fortunate enough to partner up with various sharpshooters throughout his career but Zlatan is the one he wishes he had been given more time to work alongside.
"We're friends off the field, and it's an excellent player, very unselfish. We have qualities as different as complementary and we would heard perfectly," Inzaghi told France Football.
"But I seriously injured my knee during the 2010-2011 season. Yes, not having played more with Zlatan is the biggest regret of my career."
An Ibra-Inzaghi partnership with both in their prime could have rivalled all of the great striking duos of past and present so it will always remain one of the sport's big frustrations that fans weren't treated to watching them play together more often.
Inzaghi is now well settled into his managerial career since retiring in 2012. After taking the giant leap to manage his old side during the 2014/15 campaign, he has recently taken charge of Venezia, who compete in the third tier of Italian football and are unbeaten so far this season.