Five football players that didn't retire early enough

5) Antonio Cassano

Born: July 12, 1982

Age he played till: 35 (Present)

Career: 1999-Present (Looking for another club)

A highly skilful player, the Italian international was a treat to watch when in full flow. In his prime, he could easily dribble past 2-3 players. Cassano's career kickstarted in 1999 when he played in Serie A for Bari against local rivals Lecce.

In 2001, when Cassano was just 19, he signed with Serie A reigning champions Roma for a transfer fee of 60 billion Italian lire (about €30 million). This was the most expensive teenage signing ever.

During his time at Roma, he won Serie A Young Footballer of the Year Award in 2001 and 2003. However, there were issues that were getting out of hand. In the 2005–06 pre-season,

Cassano was in constant conflict with the club management over the renewal of his contract, which was due to expire on June 30, 2006.

In January 2006, Cassano parted ways with Roma and signed with Real Madrid. for just €5 million. The playmaker's career at Real was not off to a great start. Just four months at his new club, Cassano started gaining weight due to poor eating habits.

Madrid kept fining him for every gram he remained over his playing weight. On October 30, 2006, Madrid announced on its website that Cassano had been suspended due to “disrespect” of club manager Fabio Capello.

He was subsequently benched. On various occasions, Cassano indicated his burning desire to return to Roma. He even showed his eagerness to make peace with Totti with whom he had a bitter stand-off before departing from Roma.

However, he remained with the Los Blancos after the January 2007 transfer window had closed. The rest of his season was cut short by an ankle injury, and Cassano only made seven league appearances for Madrid, scoring just a single goal.

On August 13, 2007, the Bari-born versatile player joined Serie A side Sampdoria on a one-year loan deal. Cassano had a good run at Sampdoria. However, Cassano had a heated row with club chairman Riccardo Garrone following the player’s refusal to attend an award ceremony.

He was excluded from first-team squad with immediate effect. Sampdoria applied for a contract termination to a league arbitration panel. In December 2010, AC Milan reached a deal with Sampdoria to sign Cassano.

Cassano enjoyed himself at AC Milan, linking up well with Zlatan Ibrahimovic

When Milan claimed the 2010-11 Serie A title, it was the first Scudetto of Cassano’s career, by which time, he was 29-years-old. Cassano saw further success while at Milan. After a good pre-season, Cassano won the 2011 Supercoppa Italiana with Milan over Inter.

On October 29, 2011, after Milan’s match against Roma in Rome, he suffered a stroke and was hospitalized.

He had to spend six months on the sidelines until he recuperated. On April 2nd, 2012, he featured as a substitute in Milan’s 1-2 home defeat to Fiorentina. On Apri 29th, he scored his first goal since his operation in Milan’s 4-1 win over Siena.

He also made two assists in Ibrahimovich’s goals during the match. Milan finished the Serie A season in second place behind Juventus, also reaching the semi-finals of the Coppa Italia, and the quarter-finals of the Champions League. Cassano was 30-years-old.

On August 21, 2012, Milan and Inter reached an agreement over his transfer. Cassano apparently wanted to leave the club as he was upset by the departure of key players like Ibrahimovic and Thiago Silva.

Cassano's season at Inter was marked by negativity. Not only did the club struggle in the league, but Cassano also often argued with club manager Andrea Stramaccioni. Cassano provided nine assists in the season. Inter finished the season in ninth place.

In the latter part of his career, Cassano joined Parma and then returned to Sampdoria and after that moved to Hellas Verona. Cassano has switched many clubs, but nowhere he could find the successes that he found at Milan.

Perhaps, he should have stayed at Milan where he was performing well, and also have retired from his professional career at Milan while he was still playing some good football.