Liverpool's strengths are also their weaknesses. They press relentlessly, pushing up very high and their fullbacks are extremely attacking, especially Trent. This leaves a lot of space outside the CBs that we should look to exploit. I think this is the basic gameplan, but we can do that in a number of different ways.
Most of the team pretty much picks itself but there are a few questions:
Bennacer or Tonali:
I think Bennacer needs to play this one from the start. Not sure about his condition and it's unfair on Tonali after the Lazio game, but his press-resistance and dribbling are very, very important to negate Liverpool's crazy counterpress. If we don't break that often then they'll keep pinning us back. Their midfield will swarm whoever manages to collect any loose ball and if Tonali can't escape then it will be a big problem. That used to be a big liability in his game, and i'd rather he be tested a few more times before we throw him into the fire of Anfield. As for Bennacer he's perfect for this challenge and the only issue is his fitness. It depends on how he's training but if he's fit I think he'll start.
Leao or Rebic:
This is a key question for Pioli and one that I don't think there's a right answer for. It depends on how confident he's feeling and how much risk he wants to take. Leao is probably more threatening in the sort of situations that we might find ourselves in at Anfield, but Rebic can be much more disciplined in making sure Trent doesn't overload the wing with Salah. Rebic also has a lot more synergy with Theo and they can work together to release Theo behind Trent, and that's something that Leao still hasn't mastered. I think for those two reasons that i'm leaning towards Rebic starting and Leao coming on later in the game when Theo maybe needs to sit back more. The counterargument is that we will probably want to sit back early and frustrate them and then attack later on when they start to get desperate. In that case playing Leao actually makes more sense, as we would keep Theo a bit more conservative and then later on when Rebic comes on they can tag team Trent late in the game. The fact that Rebic played an intense 90 minutes two days ago and Leao walked of after an hour is another clue that maybe Pioli is leaning towards Leao starting. Liverpool really suffer when you run at them outside their defense and manage to get some players in the box for a cutback or a drilled cross. I honestly wouldn't be surprised if Saelemaekers gets a goal this game from this sort of move.
Opportunities:
Ok so how do we exploit their weaknesses? Bennacer and Kessie withstanding their counterpress is key. They need to be able to get the ball and keep it even though two or three opponents will instantly swarm them. We're lucky that they're both ideal players for this sort of thing, but they haven't been tested against elite opposition yet. Theo is also a huge weapon here, as a counterpress means the opposition is running towards you, towards the ball, the moment you get it. If Theo can burst into space and we manage to give it to him then that's an opportunity for a Theo lung buster. Kessie is key here in making sure Theo can keep taking those risks, by protecting the space behind him in case it fails.
Maignan is going to show the world why he's going to be more important to Milan that Donnarumma ever was. Liverpool will press really high and try to close off our usual buildup routine. Maignan can bypass this with either a long direct ball into Ibra or Leao, but more importantly he's calm enough and has the technique to find Brahim in the middle, with a low pass that Brahim can instantly control and turn. He's been doing this a lot this season, where he would drop really deep to receive a pass from the defense or from Maignan by positioning himself in open space that's vacated because of practiced movements by our defensive unit. Brahim has a very good ability to turn and sprint almost instantly and this sort of transition is crucial to make sure Liverpool are defending by running back and not by running towards us and forcing us sideways or back. A midfield of Brahim, Kessie and Bennacer is as good as it gets for us to avoid the counterpress and make sure we have a way to move up.
Plan B if there's no space is to just thump it long for Ibra, and because Liverpool will have positioned themselves so high up, this means that Ibra will be surrounded by wide open space almost at the halfway line; close enough to reach reliably by Maignan. A flick on to Saelemaekers or Leao or Brahim and we're good to go. This threat will force Liverpool to ease up on the press, and this in turn will give us room to build up our usual way and move the ball up on the ground. This is something that we never could do with Donnarumma. Teams wanted him to hit it long as more often than not it's easily dealt with. Now we can punish you if you press, and we can punish you when you drop.
Defensively I think we'll do something similar to how we played Lazio; who played a very similar 433 on Sunday. Calabria in that game was playing a lot more defensively, even more so than usual. We kept Theo as the free man most of the time. Tomori, the RCB, kept close to Immobile most of the time, and Romagnoli kept an eye on Pedro, but the idea is that we tried to shift the center of gravity of our defense a bit to the left. We can do this because Florenzi was acting like an auxiliary RB and helping out Calabria, much more than what Leao was doing on the other side. This made sure that when Theo breaks he always had Leao ahead of him to pass to or to distract he defender. I think we'll do a similar thing against Liverpool, especially as there's no dedicated midfielder to track between the lines. We'll play a very man oriented system to make sure we can push up with Jota or Salah or whoever when they try to stretch us. Calabria on Mane, Kjaer on Jota and Tomori on Salah, with Theo the free man to track Trent's overloads. Robertson is slightly less attacking but Saelemaekers take care if him and make sure Mane doesn't go one on one with Calabria too often.
The more I think about it the more confident I get. Liverpool are still favorites for obvious reasons, but we really do have the tools to hurt them in ways most other teams can't. That awareness makes me think that we will play a really good game and that's probably something that will shock most people who aren't yet aware of this Milan.