Klopp always appreciated Henderson because of the importance he places on the group's attitude – but you always had a sense that it was only a matter of time before he's replaced by someone more talented, skillful, a bigger attacking threat or a more finely-tuned defensive specialist. There was one specific game where it all changed and Hendo became indispensable and I remember it pretty well, because it happened to be played on my birthday last year – 3:1 away win at Saints.
Before that game, Jordan had the audacity to have a chat with Klopp and ask him to be played further forward. Klopp's response was to drop the captain to the bench and start with the trio of Fabinho, Keita and Wijnaldum. We the fans were all ecstatic when saw the lineup with 3 of our most talented midfielders playing together for the first time, but in the game it was a disaster – they got overrun, didn't close the gaps and didn't offer enough protection to each other. We were somewhat fortunate to be tied at 1:1 when on 60th minute Klopp brought on Hendo for Gini and Milner for Trent. And this was finally the moment Hendo was given a license to attack and play as a true box-to-box midfielder – it was like "here's 30 minutes to justify your big mouth and prove I was actually playing you in a wrong position this entire time."
As they way the rest is history – Hendo set up the go-ahead goal by Salah and scored the 3rd goal in style. He went on a tear in his new position for the rest of the season, collecting 4 more assists (including a crucial one in the 4:0 game against Barca) and injecting new energy into the midfield, which helped to propel us to the CL title. Since that change in position, he's been integral to the side and we've won every major trophy we've competed for (with the exception of the EPL in 18-19 despite winning every game since). The reliable and boring 6-6.5/10 DM Henderson has been replaced by the dynamic 7-7.5/10 box-to-box player; someone does not only bring his individual qualities, but also, due to his versatility and willingness to follow instructions, acts as one of the "levers" for subtle changes to the tactical shape during the game, which has been one of our biggest hidden weapons. Another manager's ego might have made them unwilling to follow a player's lead on a tactical decision, but it was not so with Klopp and I have a sense he's gained new respect and trust for Hendo as a result of this episode (as did Hendo for Klopp, I'm sure). So yeah, that's when soon-to-be-replaced Jordan became the serial-title-winner Henderson.