In my following, nothing can compare to what the club did during Shanks’ or especially Paisley’s era. Credit to Fagan and Kenny’s 1st reign also for their short(er), but successful continuations of it.
From my following, I’d say Klopp, Rafa, Houllier. In that order.
The sad thing with Rafa is while the team gradually got better, we haven’t won anything since that '06 FA Cup. 2006-2010, zero trophies. All of his trophies came within the first two seasons. Really a shame we lost that Atletico SF, although we were close, considering the team we had out there, due to players missing.
Houllier I have respect for as he also brought progress (though sometimes it tells me more about how far behind we were at certain periods, horrible, like prisoners of our own history). My grandfather was close to him and I met him once, a very nice person.
Also some very nice trophies and a team that could be at least competitive. Able to get over the line in a lot of big games. Team full of characters I felt (although I wonder how much of it was down to that team being my first Liverpool one, so nostalgia plays a part). The Leverkusen away loss was a sad one, one of the first days I cried as a kid supporting Liverpool. Wanted United in the SF so badly, we knew how to beat them at the time.
But trophies from both managers aside, I prefered Rafa’s teams to Houllier’s. That’s pretty simple. In some aspects it wasn’t that different (both wanted solid/compact units), but when Rafa and especially Alonso came in, that was the beginning of something new. It was evident straight away. More playing out from the back. Generally a more aggressive approach. The team tactically even more together and doing more phases of the game together. Rafa’s football was much more in line with what was happening in European football, but still, you felt the club was still lacking behind that and needed to catch up.
And Klopp, well, maybe it will be best to talk about it when it’s over. But very good so far. Also, credit to FSG for bringing Liverpool at least in the present. Now we can say we don’t lack behind like we used to. Back to Klopp, playing style more protagonist than ever in my following, winning everything there is to win. Now hopefully we can win some things a few more times. Up to the club to prove post-Klopp, that they can remain being at least competitive, but also build new winning formulas. With now new directors, soon new managers, new players, etc.