AC Milan and the Emptied Right Flank: Carvajal, Guerreiro and the Free-Agent Gamble

The phone rang at 2 a.m. Liverpool time. On the other end was a contact who has walked with me for nearly two decades in the transfer-news trade. He skipped the greeting and said one short sentence: Milan have lost Saelemaekers. I sat up, switched on the desk lamp, and opened the notebook with the worn spine. Outside, the port city lay silent in the rain. In this job I have learned one thing: bad news tends to arrive at the hour when everyone else is deepest asleep, and news about an injury on the flank arrives even later, because nobody wants to announce that their club has just lost a link it never had a replacement for. Alexis Saelemaekers is the kind of player coaches quietly adore. He is not the most expensive star in the dressing room, not the face on the magazine cover, not the shirt that sells out in the club store. But he can play behind the strikers, and he can play on both wings, right and left. That versatility is exactly what turns losing him into a structural problem rather than a simple personnel problem. You do not lose a player. You lose a way of setting up the team. And when you lose a way of setting up, the price is not paid in transfer fees. It is paid in points that quietly slip away, match by match. I follow Serie A from a small flat in Liverpool, where Italian kick-off times usually drift late into the night. Some games I rewatch three times just to count how often a right-back drops in to cover the right-sided centre-back. That habit has taught me that a flank is never about one player. It is about a chain reaction: who covers for whom, who stretches the opposing defensive line, who is the first to run back when the ball is lost. The context of this story begins in the summer, not with the injury. At Milan, the flank was already at least one body short the moment the summer transfer window closed. This is the key point most bulletins skip when they fixate on the crisis headline. The current crisis is an accentuation of a flaw that already existed, not a fresh problem. When you are already short and then lose another player, you are not in crisis. You are simply paying the bill for a squad-building decision you postponed. What stands out is the asymmetry. Milan's left side is far better covered. Davide Bartesaghi remains available. A utility player like Moreira can fill in. Pervis Estupinan will eventually return from injury. The bigger issue, meanwhile, is on the right. In a 3-4-2-1, only Samuel Chukwueze is a natural right-sided option. In a 4-3-2-1, only Gila can do the job. That is a level of thinness that makes any coach sweat. I want to pause here on how I read such numbers. When a club has exactly one natural option for a position, the pressure does not show up in the big match. It shows up in the small one, the game where you must rotate, the game where you must protect your key men for the run ahead. That is the moment a thin flank becomes a tactical hole that can be exploited by the simplest counter-attacks. The opponent does not need to be brilliant. They only need to look toward your right side. There is a line I always remind myself of before writing anything: I do not believe in rumours, I believe in sources that have walked with me for twenty years. With the Milan story, I have to apply that principle strictly, because the data set in front of me contains three integrity problems any careful reader must know before trusting the conclusions. The first concerns the coaching staff. The material I analysed states that the injuries will force a manager named Ruben Amorim to rethink his plans. But in my public record, there is no entry showing Ruben Amorim ever managing AC Milan. This is either an error in the original source or an extraction error in editing. Either way, all coaching-dependent analysis must be downgraded. I will not build a tactical conclusion on a name I cannot verify. The second concerns the timeline. The material says Saelemaekers' 2026 is already over, and that a return is not expected before the start of 2027. Those dates place the story in an unusual timeframe. I record them exactly as written, but I stay cautious about any scheduling reasoning built on them. In my trade, one wrong day can ruin a bulletin, and one wrong year can ruin a career. The third is source quality. The material contains self-promotional content urging readers to add a site as a preferred source. That has zero analytical value. I remove it from every calculation, because the transfer market is already full of noise, and my job is to filter noise, not amplify it. On the reliability hierarchy: a club statement about Saelemaekers ranks high. Author analysis and opinion rank medium. A quote from an unnamed source about Estupinan ranks low. And reports that a free agent has been offered around rank medium-low, because they are usually pushed by the agent rather than the club. When I string it all together, the picture sharpens. This is the story of a club trying to plug a hole with short-term fixes, including the free-agent market. And in that market, two names surface: Dani Carvajal and Raphael Guerreiro. Take Carvajal first. At his age, people tend to judge him by his trophy list. For me, the real question is not the medals. It is the system fit. Carvajal is better suited to an orthodox right-back role in a back four than to a wing-back role ahead of a back three. That tactical detail carries enormous weight, because it triggers a chain of consequences. If Milan sign Carvajal to play his natural role, the club is almost forced to switch to a back four. But switching to a back four thins the wide-forward depth even further, exactly the area already short of bodies. You solve one problem by creating another. That is the nature of emergency recruitment: you never buy a perfect solution, you only buy the least bad one. Conversely, if Milan keep the back three and push Carvajal into a wing-back role, you have a top-class player operating out of position. At his age, asking a right-back to run the flank for ninety minutes in a physically punishing system is a gamble on the body. And this is where my professional memory speaks up. I have spent my career watching how players past thirty cope with ever-rising intensity. Their bodies do not fail all at once. They degrade match by match, extra time by extra time, night flight by night flight after away games. A top full-back at thirty-five can be superb for thirty minutes, but by the seventieth, the gap between him and a twenty-two-year-old becomes a chasm the eye struggles to see but the data never misses. That is why I always look at sprint counts, accelerations over the final thirty metres, and second-half duel success. Without those numbers, any judgement of an ageing full-back is guesswork. And I do not write on guesswork. Now Raphael Guerreiro. He is the versatile type who can play full-back or wide midfielder, on either side. In theory, he is the perfect piece for a club needing flexibility. In practice, he is a similar gamble on fitness, differing only in that he offers more positional options. What I like about a Guerreiro-type option is that it preserves the system. You do not need to change the shape to slot him in. He adapts. In modern football, a player who can occupy two positions within one match is worth double a single-position specialist, because he gives the coach the power to change the game without spending a substitution. But I have to say plainly what few want to hear. A free agent is never truly free. His price sits in wages, in signing fees, in age, and in injury risk. When you pay no transfer fee, you pay in another currency. It might be a long contract on high wages for a player past his peak. It might be a large agent commission. The free market does not erase cost. It moves cost from one line of the balance sheet to another. Agents tend to call at the hour when everyone else is asleep. That is why I read free-agent offered reports closely. The motive behind them is rarely a desire to help the club. It is a desire to create a race and drive up the price. When you see two clubs linked to the same free agent on the same day, chances are it is an organised media campaign, not a real negotiation. With Pervis Estupinan, the story is different. Here the information comes from an unnamed source. In my trade, an anonymous source is only as valuable as the person quoting it. If it is a journalist I have verified over years, I weigh it. If it is a vague source in an unclear chain, I note it and set it aside. Estupinan may be a good tactical option, since he is an attack-minded left-back. But signing a left-back to solve a right-flank problem is a logical muddle, unless the club intends to reshape the entire structure. I once watched a Premier League club sign a left-back in January to plug a right-side hole. They ended up with a player out of position for half a season, his attacking numbers halved, and by season's end he was sold off. The lesson is simple: the right player in the wrong position is still wrong. Football does not reward artificial flexibility. On the left, Milan are actually in a healthier place. Bartesaghi is a young talent who needs protecting. And here my core view on youth development speaks. I have always held that early-developing youngsters are overused. A body not yet matured, pushed into adult intensity, playing every three days, travelling constantly between cities, carrying the pressure to win now. That is the formula for chronic injury before twenty-five. Bartesaghi may be a short-term fix, but if Milan push him into covering an entire flank, the club trades his future for three immediate points. Moreira, as a utility player, offers a stopgap. But a stopgap is not a build. A utility player in a non-natural position will defend competently but create no attacking spark. In modern football, a full-back who only defends is a full-back slowing the whole team. Big clubs no longer field purely defensive full-backs. They field players who create numerical advantage up the pitch. Samuel Chukwueze is the most natural right-sided option in a back three. But placing him at wing-back demands a big defensive compromise. Chukwueze is an attacker. Asking him to drop and shield the flank all game wastes his talent and creates defensive risk. This is one of the most elegant paradoxes of tactical football: to fix a defensive flank problem, you sacrifice attacking width, and vice versa. As for Gila, he can only cover the right side in a back four. That means if Milan want to use him, they must switch to a back four, dragging along the same consequences I analysed in Carvajal's case. You see, every option leads to a tactical fork, and every fork has its price. Now I want to spend the rest on what I call the blind spot of the official story. This is where a real transfer reporter works hardest. The first blind spot is the manager story. In the material I analysed, a name is attached to the Milan manager role, but that name matches none of my public records. I raise this not to score a point. I raise it because it reminds us that even professional bulletins can carry errors, and readers deserve to know when a conclusion stands on shaky ground. If the manager's identity is wrong, every analysis of the manager's plan becomes a building on sand. The second blind spot is the timing story. When a document says a player's season ended in 2026 and a return before 2027 is unlikely, the reader should ask: is this a forecast, a mistake, or a special situation? In my trade, I have seen injury forecasts reversed within weeks. A player ruled out for the season can return early. And a player reported to be recovering fast can re-injure on his first game back. Time in football is not a straight line. It is an uncertain curve. The third blind spot is the free-agent trap. When a big club faces a squad crisis, public opinion turns immediately to free agents, as if that were a miraculous, cost-free solution. But professional clubs know that a free agent at his peak is an extremely rare case. Most free agents fall into one of three groups: those past their peak, those with lingering fitness issues, or those whose wage demands exceed their true value. Sometimes they fall into all three at once. That is why I always check a free agent's injury history before judging him. I count the games he missed in the last three seasons. I look at how many minutes he plays per week. I look at how often he leaves the pitch mid-match. Those numbers tell a more honest story than any agent's pitch. Every contract is a life waiting to be written onward. That is what I remember when I look at a name in a bulletin. Behind every name is a family weighing a move, a child changing schools, a spouse learning a new language, a player leaving the place he belongs. When you write about transfers like a video game, you forget you are writing about people. And when you write about people, you must write with respect. Hearing the crying through the screen, I understand football is a matter of the heart. I once sat in a cafe in Hanoi watching dozens of fans break down when their team lost a match that, half a world away, none of the players knew had broken the hearts of people they had never met. Geography does not dull emotion. It only makes it lonelier. That is why I always ask, after every transfer analysis: what does this mean for the fans in Vietnam and England? For Milan fans in Vietnam, those who stay up all night to watch their club, the story of an emptied right flank is not a dry tactical puzzle. It is the fear that the team they love will drop points in games they should win. It is the helplessness of seeing the problem but being unable to fix it. I spent years building a Liverpool supporters' community in Vietnam, where I hosted online sessions on club finances and how financial fair play shapes transfer plans. Through those, I learned that fans do not need to be taught. They need to be heard. They understand football in their own way, and their way is often more practical than the experts'. When I explained why a club must extend a key centre-back rather than buy an attacking star, thousands understood instantly. They only needed someone to explain it in human language, not spreadsheet language. Back to Milan. This story, in the end, is the story of a club trying to patch a hole that has existed since summer. The options floated — Carvajal, Guerreiro, Estupinan — are all short-term. None solves the root cause: that the club entered the season with a flank thinner than required. And here is the contrarian angle I want to leave. When a club hits a squad crisis at one position, the natural reaction is to buy a player for that position at once. But the right reaction is sometimes to accept a system change that hides the weakness, rather than force a new player into a system that does not suit him. A good coach can turn a short squad into a smooth machine by adjusting how it plays. A weak coach buys a player and forces him into a role that is not his. Football history is full of failed deals for this reason. Clubs sign good players who do not fit, then blame the player when results do not come. The truth is that most failed deals fail not because the player is poor. They fail because the club bought a player for a system that does not exist, or for a system the coach does not truly want to play. For Milan, the real question is not whether to sign Carvajal or Guerreiro. The real question is whether the club wants to play with a back three or a back four for the rest of the season. When that answer is clear, the name to sign reveals itself. When the answer is vague, every deal becomes a gamble. I have spent twenty years watching the transfer market, and what I learned is that the market never rewards haste. It rewards patience, clubs willing to wait for the right moment, people who know that one right player in January beats two wrong players in August. Saelemaekers will return, whether late this season or early next. The question is where Milan will be when he does. Some mistakes are worth more than a hundred exclusives. And the biggest mistake in the transfer market is not signing the wrong player. It is signing the right player at the wrong time, for the wrong system, for the wrong reason. The phone will ring again at 2 a.m. Some agent will call, and a new name will appear. My job is to listen, verify, and write only when I am sure. Because in the transfer market, timing is the brand, but the truth is the legacy. And for Milan fans in Vietnam and in England, those who stay up all night for their club, they deserve the truth, not a pretty headline. A season without fans in the stands never lacks the sound of heartbeats. At Milan, those heartbeats are turned toward an empty right flank, where a new name will soon be written, and where a new life will begin. Will the club choose the short-term safety of a free agent, or the long-term patience of the right solution? The answer will come on some late night, when my phone rings again, and I must decide whether to speak up or stay silent once more.