Milan Season Preview 2023-24

Here we are…finally! The Milan 2023-24 Season Preview. After all the talk, grandstanding, rage, joy, and everything in-between, we finally get to see what it all means on the pitch.

In the previous post we got to hear from other Calcio fans in our Behind Enemy Lines: Serie A Top 7 Preview, but now we get to discuss Milan and everything that transpired over the summer and what it all means for the upcoming 2023-24 season. While most of this preview will be forward-looking, we do touch some on what happened the day after last season ended and how it shaped this summer’s mercato. As you can tell from the post graphic at the top, I think Gerry is, was, and will be the main factor this season.

So, what do we have in store for you? Rather than a position-by-position preview or running through all the names of new players this season, which we feel we’ve covered here, here, and here, Michael Lisi and I had a conversation about Milan. We asked each other the same 5 questions we asked our guest contributors in the top 7 preview, but we talked more in-depth and were able to have a dialogue where we felt the topic needed more context or insight. We also went through a series of quick-hitting questions looking at some MVP predictions and things of that sort. We end our chat with the 5th and final question, making a prediction for the top 7 and who we think will get relegated.

Let’s get started!

Who do you think Milan's best player acquisition was this summer?

Michael Lisi: The best player I have seen on the field so far is Pulisic. His patience and vision and playmaking is ahead of everyone else we have seen so far. The width and wisdom he will provide in multiple spots is far and away above anyone else we currently have on the team. The issue of where exactly he will play is slightly overblown. The fact that he can play almost anywhere in the attack is what really matters. He can cross, shoot, take guys 1v1 and also draw a foul. The penalty he drew in our last major friendly is a perfect example of the soccer IQ he possesses.

I would put a Reijnders only slightly behind him in term of ready-made-impact. He was dropped into the midfield straight away and looked like he had already been here 4 years. His passing and vision is something we’ve lacked for a while now. That all being said, in 2 years Chukwueze might be the best signing of the summer. His ceiling is easily the highest. He COULD be this year’s Kvara. His speed and take on-ability is that high. That’s a 50 million player we stole for 20 million plus add-ons.

gillis15: I like all the guys you mentioned and the reasons you gave. I’m not quite as sold on Reijnders but that’s partially driven by not really knowing him, not seeing anything special from the preseason friendlies, and while I’ve come across some highlights I, (1) am skeptical to just go off of those because he’s coming from a smaller league, and (2) I WILL NOT trust another YouTube highlight reel after Hakan…

For me, the best player acquisition is Yunus Musah. He may not show it all this season so maybe he wouldn’t be my pick if it was just for the upcoming season, but the upside is huge. He’s never going to put down massive stat lines with goals and assists but I very much see him being a Tonali-type of player but more physically gifted. He’s strong, fast, and can grow his game on all levels: defense, offense, possession, passing, scoring, all of it.

Michael Lisi: I have big hopes for Musah but they are based on more hype than the reality of watching him play. I’m hoping he comes in and demands that job right away. Kessie 2.0 I hope. We really need that midfield to be firing on all cylinders as soon as possible. Next question!

What do you think will have the biggest impact on Milan's success this upcoming season? This can be the transfer market, coaching (either new coach or no change), formational change, current player growth, really anything

Michael Lisi: The backline. I think with all the moving parts in the midfield and attack, the defense has to be rock solid. The more Thiaw and Tomori play together the better they should become. Theo is rock solid. Kalulu is quality and can play multiple spots. Calabria is what he is. Is that the polite way to say he’s bang average? It helps that behind them we have the best keeper on the planet. Thank you Maldini for finding Maignan. As long as that group can cover up the back that should paper over any growing pains we have in other places. Musah jumping right into that DM role would certainly help as well.

gillis15: You hit on what I think is the solution to my answer to this question and that’s the midfield and all of these moving/changing pieces. Specifically, I think the midfield turnover is what impacts this season the most. Specifically, I’m concerned not only with the newness of the midfield but also how the players and their characteristics fit together. I’ve commented in a couple of posts this summer and in the chats that I’m worried about too many of the same type of midfielders and where the creativity is going to come from. I’ve heard that Reijnders is that guy, and as I just elaborated in the first question, I’m not convinced he is but I hope so!

If Reijnders doesn’t pan out or takes a long time to adjust, and Pulisic doesn’t find a place, then we’re back to having a solid back line and keeper, a game-changing forward, and nothing in-between to link them. Last season the midfield guys played a lot of backward or lateral balls and had a lot of difficulty advancing the ball vs high-pressuring teams. Brahim would often work his way back to help provide an outlet, either from the CAM position or he would come in from the right when he was played as a right winger. He’s obviously gone now so what are they going to do? Feels like we might be back to: Milan wins the ball back deep in their territory and then someone – probably Maignan, ends up kicking 50:50 balls down hoping one of the forwards can do something with it. Not exactly inspiring.

I don’t know, what do you think? Are you as concerned and pessimistic as I am on this?

Michael Lisi: Totally understand, it’s easy to get sucked into the hype of buying new guys. It’s probably like hitting up Tinder every night.

I have been notoriously ever-positive ever since showing up here way back when. I was able to talk myself into guys like Mati Fernandez and fucking Mesbah for God’s sake. Even Bonucci felt like a good idea for at least a month or two. My optimism comes from the quality of signings and depth we now have. Pulisic is plug-and-play. As is RLC. I think Reijnders looks ready though the summer should always be taken with a grain of salt. Remember we won the scudetto with almost no depth. We made the Champions League semis before that lack of depth finally caught up to us. So, the depth of quality does have me excited. As does Pioli’s ability and willingness to try new things. My fear is we start slow and management takes that opportunity to fire Pioli. I don’t think that will happen but it’s not outside the realm of possibility. Until we know this new management team it’s hard to have 100% faith in them. The summer window was a great start.

What are you most excited and least excited about for your team this season?

Michael Lisi: I’m most excited that the season is starting. I know that sounds like a cop-out but I hate the summer. HATE IT. The transfer windows are the most boring thing in the world to me. Please lord play some games!!! It’s just a bonus that for once I’m happy with the window and I’m excited to see what Papa Pioli will do with all these new toys.

Least excited. Hmmm. That’s tough. If anything I’m least excited about seeing Calabria out there for another year. Granted he pulled a masterclass against Kvara but I think he might be the weakest spot on the team. The sooner Kalulu takes control of that spot the better. I know he had a bit of a howler last season but I don’t think that he’s a bust or anything. As they say ‘form is temporary, class is forever’.

gillis15: Stop taking my talking points! Calabria was one of my least favorite picks as well, one of two actually, but since you talked about him let me focus on my other: the 4-3-3 formation. I hate this idea and not only do I like the 4-2-3-1 more I actually think Milan’s squad is better suited for it. But it’s even more than that. I think with Kalulu starting at RB then the backline could be as good as it was during the second half of the Scudetto season. A healthy Maignan obviously helps that. If they are then Milan can afford to get more aggressive getting forward, and with my creativity concerns in the midfield, then Pulisic can find a home at CAM and help with that.

The final thing I’ll say about my dislike of the 4-3-3 are having two inverted wingers potentially starting. I’ve found that inverted wingers tend to cross into the box less…because they’re looking to cut in on their stronger foot and get shots off…and with that comes the greater potential of having less width in the formation and doesn’t provide consistent service to Giroud. That’s never ideal and it works against Milan’s best attacking option: getting Leão into space.

On the thing I’m most excited about, well, that has to be all the new young players, something I wasn’t convinced of seeing after Maldini was fired since I didn’t know what direction Cardinale was going to take them. There’s a lot of moving pieces and lots of things have to go right for these guys to reach their full potential, but there’s no doubt there’s a lot of talent on the squad and I like the unknown when it’s striped with talent and upside.

Michael Lisi: I see your point. Right now I am choosing to believe that having all this flexibility is a blessing. Especially during a long league season. It is only that to a point though. To win the biggest games you have to know who your best XI are and how they fit together. It must be clear. Like the old saying goes, if you have 2 starting keepers you got NO starting keepers.

Where do you think Milan will finish this year and do you think they'll win any trophies?

Michael Lisi: We will win the Scudetto. Mark it. We will blow off the Coppa as usual. Something tells me we struggle in the Champions League though. I’m probably only saying that because we did so well last year and the competition is so random. We will know more on that once the Champions League draw comes out.

gillis15: Wow. Ok. That’s higher than I have Milan this season but I’m still struggling with this. Ultimately, I can’t go that far because I think they might drop too many points out the gate and that’ll end up costing them the Scudetto. There’s zero doubt Milan is more talented this season. Maybe more talented then they have been in 10 years. So, while the floor is certainly higher, I don’t know that the ceiling is because of too many similar pieces brought in this summer, mostly pertaining to the midfield. I think they’re a stronger candidate to finish in the top 4 with more margin for error, but I don’t think they’ll do as well in Champions League in part because of the composition of talent…and yes, it’s difficult to make consecutive deep runs in Champions League unless you’re Pep and have a €2 billion squad. I agree with you that they’ll blow off the Coppa.

Ok, I know I didn’t answer-answer the question yet so here I go…I think they’ll finish 2nd in the league, reach the quarterfinal in Champions League, and get to the semi-final in the Coppa. Not a bad year at all but no trophies unless the Silvio Berlusconi Cup counts?!

I don’t know. This is a tough one. I wouldn’t put them second had there not been some drop off with the other top 7 teams from last season. It’s hard to repeat as champs so I don’t think Napoli wins the Scudetto. Inter has dropped off and I don’t think Juventus does much with all this fraud and scandal-stuff hanging over them still. Tough call this year!

Michael Lisi: Second star incoming. Telling YOU!!

gillis15: I hope so! There’s no better way to be wrong than underestimating your team and they surprise you with a trophy.

Ok, let’s end with some quick hitters before the 5th and final question we asked the group…

Quick Hitters

Team MVP?

Michael Lisi: Leão. Sexy beast. 20 goals.

gillis15: Maignan.

Most improved?

Michael Lisi: Kalulu. He’s starting by Christmas and the best RB in the league by season’s end.

gillis15: I like! I’m going with Thiaw. I think he’s a top 5 Serie A CB by January 1st and I think he nets 5 goals for the season. Kid’s a stud in the air.

Best new player?

Michael Lisi: Oh boy that’s tough. I think that is gonna change a few times as the season goes on. I think the first half of the season it’s RLC/Reijnders because they settle the midfield. Then as time goes on Chukwueze claims the RW spot and bursts on the scene as the runaway newcomer of the season.

gillis15: I’m going to homer this pick and say Pulisic.

Michael Lisi: HOMER!!!

gillis15: Total homer.

Best Keeper?

Michael Lisi: Maignan, of course.

gillis15: Of course.

Best defender this season?

Michael Lisi: Kalulu. No, Theo. Best LB in the world.

gillis15: Theo is solid. I’m going with Thiaw.

Best midfielder?

Michael Lisi: I think overall it will be Reijnders. RLC might be better but he will miss time. Dark horse being Pulisic if 4-2-3-1 sticks.

gillis15: I was leaning towards RLC as well. I think Musah might be the second half of the season.

Best attacker?

Michael Lisi: Leão for sure but Chukwueze nipping at his heels by the end of the year. I’ll be very interested to see how well they play off each other.

gillis15: Yeah, it’s Leão for me as well because with a better supporting cast, look out. Do you think he can hit a combined 30 goals/assists in league play this season? He had 21 during the Scudetto year, 23 last season

Michael Lisi: No doubt. 20 and 10 should be in the bag this year. Should be a lot more opportunities for assists this year for him, better players to pass to.

Does Pioli make it through the season?

Michael Lisi: Oh boy. That one has been running through my head all summer. The day after Maldini left I would have bet my life he was gone. As summer has gone on though I think these guys appear to be competent and reasonable. Hold on there’s more…

I think bigger clubs in Italy have learned that firing guys mid-season almost never goes well. It would have to be a Giampaolo-like disaster for that to happen. I don’t think that will happen under Pioli. He’s not so stubborn to watch it all crash and burn just to jam his style down the team’s throat. I think he will be ok. Next!

gillis15: I think he makes through as well. Heck, he’s turning into a unicorn. How many Serie A coaches have more than 3 years the helm Pioli…Gasperini…Mourinho. I know Allegri has a long-combined tenure at Juve but not this stint.

Michael Lisi: It’s year 3 for Mourinho. Usually when he implodes.

gillis15: Oh yes, he’s in year 3. When his theatrics finally run him out of town.

Michael Lisi: Stay tuned.

With how the summer started, literally the day after last season ended, Maldini was fired and the Milan-world of the last 3 years was over. Now that we’ve all had some time, what are your thoughts on the official start of the Gerry Cardinale AC Milan era?

Michael Lisi: Dare I say so far so good. These guys had a plan and have stuck to it all summer. They’ve nailed almost every target they had. We bought 3 wingers, a striker, and an entirely new midfield for right around 100 million. That’s impressive considering they basically just spent the Tonali plus the Champions League money we made last year. They didn’t have to go into the red at all. That and they probably lowered the team’s wage bill. I would give them an A- so far. The only thing they can do to bring that up would be to sell off Origi.

gillis15: For better or worse, Gerry Cardinale made this all about him. Everything. This won’t be like the Chinese ownership or some other group that bought some other team and are otherwise unknown. No. When you do something like this, fire a legend and one that had returned Milan to glory, you’re deciding to put the spotlight all on yourself. Forever. Every move will be scrutinized through this lens for as long as he owns the team and doesn’t reach the highest pinnacle of the sport. Rant over.

Ok, my take on the situation is that Milan have improved but I don’t know that they’re better, as in being closer to lifting the Champions League trophy. They’re certainly deeper, as we’ve touched on, and I think that makes them a better bet to remain in the top 4, which is important.

But if it was me and I could’ve spent the €110M I’m probably sticking with the plan during the Maldini era, getting some really young and unknown guys for a combined €20M, a couple of starting midfielders with different characteristics for €40M, and then getting an established young star at RW for whatever is left – €50m-ish or so. I’m talking a game-changing type. The team stays young and stocked with young promising talent, you help the current starting midfield, and you REALLY strengthen the attack. Easier to work in 4-5 players than 8 and you still improve and add depth. I don’t know, just my two cents.

Ok, onto the 5th and final question.

What's your prediction for top 7 in Serie A this season? Extra: Who's getting relegated?

Michael Lisi:

1) Milan
2) Napoli
3) Inter
4) Juve
5) Lazio
6) Fiorentina
7) Atalanta

18) Cagliari
19) Frosinone
20)Verona
FUCK ROMA!!!! Mourinho can suck on DEEZ NUTS.

gillis15: Damn. Thinking about this again and the other teams and all the holes they have, maybe Milan is going to win the Scudetto! But, since I’ve already said they’d finish 2nd I’ll stick with that. Here’s my top 7 and bottom 3:
1. Lazio
2. Milan
3. Napoli
4. Inter
5. Atalanta
6. Juventus
7. Fiorentina
(I’m with you, eff Roma and Mourinho)

18. Salernitana
19. Verona
20. Frosinone

I honestly think it’s a crap-shoot this year and any of my top 4 teams can win it, maybe even Juve playing in only one competition assuming they get disqualified from Europa. Plus, I like the idea of 5 different Scudetto winners over the last 5 years. That’d be good for the league.

Wrap Up

That was fun! With so many Milan previews out there, many of which just run together because they’re basically the same, we hope you all enjoyed this as well. Most importantly, all of this pontificating means the season is near and we can’t wait for the games to get started! Be on the lookout for Lisi’s first Serie A League Whip-Around of the new season. Until then…

FORZA MILAN

gillis