Grimaldo's departure to Leverkusen leaves a void that will not be easy to fill. With four National Championships, one Portuguese Cup, one League Cup, and three Cândido de Oliveira Super Cups, the Spanish player has left an almost unparalleled legacy of quality and success. His 294 appearances and 26 goals for Benfica place him alongside legends such as Pietra, Veloso, and Álvaro.

In the 90s, the left-back position experienced a period of less prominence after the alternating performances of Veloso and Kenedy. Players like Dimas, Pedro Henriques, El Hadrioui, and Scott Minto failed to leave a lasting impact. It was only in 2003, with the arrival of Greek player Takis Fyssas, that Benfica once again had a high-quality left-back. Fyssas, who won the European Championship in 2004, spent two seasons at Benfica, winning a league title and a Portuguese Cup.

The Brazilian Léo took over the position in the 2005/2006 season and provided solid defensive skills and attacking ability. With 127 appearances, Léo holds the record for the most games played by a left-back for Benfica. However, subsequent signings like Dos Santos, Miguelito, Sepsi, and Schaffer failed to make a lasting impact.

It was under the guidance of Jorge Jesus that winger Fábio Coentrão was converted into a world-class left-back. After two successful years at Benfica, Coentrão was transferred to Real Madrid for a staggering 30 million euros in 2011. Despite several unsuccessful experiments with other players, the balance was finally restored with the arrival of Brazilian defender Siqueira from Granada.

But Siqueira only stayed at Benfica for a year, and the subsequent arrivals of Eliseu and Grimaldo marked a period of success from 2014 to 2019. Grimaldo, in particular, established himself as the undisputed left-back, making 240 appearances and scoring 24 goals. Although Nuno Tavares, Ristic, Yuri Ribeiro, and Sandro Cruz had short stints at the club, they failed to overshadow the Spanish player.

Now it is David Jurásek's turn to try and erase the memory of the unforgettable Grimaldo. However, it is worth noting that Ristic has made an impressive start to the pre-season.