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He did so with remarkable regularity across his nine years as manager of the club, though his words have perhaps never resonated as profoundly as they did on Thursday, after Liverpool forward Diogo Jota, 28, and younger brother André Silva, 25, were killed in a car accident in northwest Spain.
"This is a moment where I struggle," Klopp wrote on social media.
Alongside the hundreds of heartfelt tributes left by Liverpool fans outside Anfield, there are marks of respect from fans of Manchester United and Everton.
That supporters of the Reds' two fiercest domestic rivals have taken the time to honor Jota's passing is reflective of football's ability to transcend the world of sport.
But Jota soon proved the doubters wrong, scoring seven goals in his first 10 appearances for the club, matching the record set by legendary striker Robbie Fowler.
Under Klopp, the forward became an indispensable part of one of Europe's most formidable attacks and, while a succession of injuries limited his game time at Anfield, he still cultivated a legacy as a key player in a golden era for the club.
Fans at Anfield have laid tributes to Diogo Jota. Peter Byrne/PA Images via Getty Images
Across his five seasons at Liverpool, Jota scored 65 goals in 182 appearances and won four major honors; two League Cups, one FA Cup and, most notably, last season's Premier League title.
He scored 14 goals in 29 appearances for his country and, though he perhaps lacked the overt star quality of some of his more well-known teammates, he remained a highly valued and well-liked member of the squad.
Portugal captain Ronaldo was among the first to pay tribute, writing on social media that Jota's death "doesn't make any sense." While the sporting world mourns Diogo Jota the player, those who knew him best are grieving Diogo Jota the husband, son and father.
Born and raised in Portugal, Jota's rise from a youth player at local side Gondomar to the heady heights of the Premier League was an inspiration to many in his homeland and, in 2022, he returned to his boyhood club to open a football academy in his name -- a gesture designed to give back to the place where his journey began.
Less than two weeks ago, the 28-year-old married his childhood sweetheart and the mother of his three children, Rute Cardoso at a ceremony in Porto.
In an Instagram post marking the occasion last week, the pair shared photos of their young family alongside the caption: "Para Sempre" ["Yes to forever"].
During his time at Liverpool, Jota was afforded the ultimate honor of a terrace chant to the tune of "Bad Moon Rising" by Creedence Clearwater Revival.
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