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Jurgen Klopp did not leave Liverpool with any regrets. On the contrary, he left as the man who turned a fallen giant into a Premier League, European, and World champion, having also laid the foundations for even more success.
There can be no doubt that his legacy at the club is secure forever. If anything, success for Arne Slot is only mythologizing Klopp further, cementing him as the modern Bill Shankly to Slot's Bob Paisley.
But after close to a decade at a club, every manager will have accumulated a whole catalog of "what if" moments, both good and bad. Klopp famously had to be convinced to go for Mohamed Salah over Julian Brandt, while he will never forget the 11 millimeters that sent the title to Man City.
Along with his transfer team, Klopp certainly got the biggest recruitment calls right. As well as Salah, he brought the likes of Sadio Mane, Virgil van Dijk, and Alisson to the club.
Naturally, however, there were countless passed-up opportunities for every player signed. And Klopp ignored the advice of a Liverpool cult hero when it came to Dayot Upamecano.
Now at Bayern Munich, Upamecano is being linked with Liverpool in earnest, amid an uncertain future for Ibrahima Konate. But Peter Crouch was suggesting the Frenchman way back in 2021:
"Everyone in football can see that they need a center-half," Crouch said of Liverpool back in 2021, amid the depths of the infamous injury crisis. "You’d think they would bring someone in before the deadline.
"But we can’t criticise Liverpool’s transfer policy," Crouch continued, speaking on talkSPORT. "It’s been unbelievable over the past couple of years, the players they’ve brought in and have improved.
"There are so many top centre-halves out there. Upamecano is a top centre-half, I think he’s one of the best in Europe — he’s the best one out there if they can possibly get him."
Instead, Klopp ended up settling for Ben Davies, and a loan for Ozan Kabak. The former never played a single minute for Liverpool, although he was sold on at a profit, while the latter disappeared off the radar after the Reds elected not to make the move permanent.
It's easy to say in hindsight that Crouch was right. There's no doubt that Upamecano would have been a better addition than either of those two.
But whether he would have been available from RB Leipzig at that time is another matter altogether. And crucially, by electing for temporary solutions in the winter, Klopp was able to extract Konate from Leipzig in the summer.
Nothing that's happened since has done anything to show Klopp that this was the wrong choice. Upamecano left for Bayern Munich that same summer, and he and Konate have followed pretty equivalent trajectories since then.
So much so, in fact, that both are in the midst of contract sagas. Neither have renewed at their respective clubs, and both can negotiate with foreign sides from January.
On a free transfer, Slot should certainly think about taking the advice that Klopp ignored. Whether as a Konate replacement or as a means of reuniting the pair, Upamecano would be a shrewd pick-up.
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