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#3 Argentina retirement
We may never see Lionel Messi get as emotional as he did after losing the Copa America final in 2016. Having lost three finals with Argentina prior to that period, the attacker's appearance in that game represented a huge chance for him to overcome his nightmare.
However, the Albiceleste fell short once again to Chile. Both sides failed to find the back of the net after 120 minutes and the match headed into a shootout. Lionel Messi stepped up to take the first spot-kick for Argentina but failed to find the target.
The shootout ended with a 4-2 scoreline, with Chile coming out on top. The pain of losing his fourth major final at international level proved to be too much for Leo to bear. The attacker announced his retirement from the national team after the tournament, although he later returned and finally had the last laugh this summer.
#2 World Cup failure in 2014
The 2014 FIFA World Cup ended up producing the worst nightmare of Lionel Messi's career. The playmaker was incredible throughout the tournament, with his four goals and one assist helping Argentina progress into the final, where they faced Germany.
With nothing to separate both teams after 90 minutes, the game headed into extra-time. Many were expecting a shootout to decide the winner, but German attacker Mario Gotze had a different idea.
The former Bayern Munich superstar stepped up and scored the only goal of the encounter in the 113th minute. Had Leo triumphed in that match, the debate over who is the greatest player in history would've been long concluded. It was really an emotional night for the attacker and he couldn't help but give in to tears.
#1 Barcelona departure
Lionel Messi's association with Barcelona was viewed as a perfect marriage for many years. That's why his departure from the club this summer is one of the moments that even opposition fans wished never happened.
It all began in the summer of 2020 when the Argentine sent in a burofax stating that he wanted to leave. Although he stayed put, that episode strained his long-standing relationship with Barcelona.
The inevitable finally happened this summer. Despite being willing to continue at Camp Nou, the Blaugrana couldn't afford to tie him to a new contract due to their poor financial state. Hence, Lionel Messi was forced to end his 21-year association with the club, joining Paris Saint-Germain after his departure.
