Starting as a Defensive Midfielder at Real Madrid

Chapter 60: Eliminated from the Champions League, Still Fighting on Two Fronts

"We won!!! Let Napoli go to hell! Forza Milan!!!"

Boateng's unfiltered post-match celebration made every Milan player break into a smile.

Physically, they were already exhausted. But mentally, they were on a high, reveling in the joy of victory.

Leon, especially, was swarmed by his teammates with relentless praise and celebratory roughhousing.

He couldn't help it—his performance on both ends of the pitch had been absolutely explosive!

A goal and an assist, with that final interception and piercing through ball to Pato simply too precise, too unexpected.

Pato still couldn't quite believe Leon had actually sent that pass through to him. It felt unreal.

Among all the players in Milan, perhaps only Pirlo truly understood: Leon had now developed the ability to deliver such dangerous passes.

Still inconsistent, with a high demand for timing and spacing, but the technical foundation was there.

Leon's short passing had improved to the point that even Pirlo could say with some conviction: "Not bad."

In other words, the raw materials were there—it was just a matter of practice.

Once Leon could turn these "flashes of brilliance" into regular weapons, the media's evaluation of him would definitely rise another tier.

Pirlo estimated that mastering this kind of incisive through pass in a counterattack would take Leon another one or two seasons.

After all, there's a vast difference between learning a skill and mastering it.

It would take many matches, and a lot of time on the training ground.

For most young players, Pirlo would estimate three to four seasons.

But for Leon…

Thinking about how Leon got jittery if he skipped even one day of extra training, Pirlo couldn't help but laugh and shake his head.

This kid? One or two seasons was more than enough.

"Take down Napoli, then take down Inter—and we'll be on our way to clinching the title early!"

Pato had jumped onto Leon's back, exuberantly shouting to his teammates.

Technically, between now and the second leg against Inter, Milan still had to face tough opponents like Juventus and Palermo.

But the confidence among the Milan squad was sky-high.

They weren't expecting to go undefeated all the way, but Allegri's bold proclamation—"undefeated in the second half of the season"—suddenly didn't feel like such a stretch.

Hearing the fans' ecstatic chants echoing around the stadium, and seeing his teammates flushed with victory, Leon chose not to mention what was on the tip of his tongue: "There's still that Champions League match."

Why bring up the sore subject?

Especially since he wouldn't even be playing. He'd just be watching from home. Better not to mention it at all.

That evening, Gattuso and the still-recovering Ambrosini invited the entire Milan squad to a private restaurant in the city to celebrate.

Plenty of wine was poured, and the atmosphere was electric.

Leon, a little out of place, quietly ordered a glass of freshly squeezed orange juice.

But the veterans liked that about him. It showed discipline and focus.

They shot him approving glances, then sighed as they turned to see Pato already getting rowdy with Boateng, arms draped over each other, clearly tipsy.

Ambrosini, the veteran captain, left a good impression on Leon—warm, friendly, not at all arrogant.

Leon found himself wishing Paolo Maldini had been able to attend. He would've asked for an autograph, and maybe even gotten a tip or two about executing the elegant slide-tackle-and-retain move Maldini had mastered.

He'd been longing to master that technique himself and was only now starting to pick it up through training with Nesta.

But it was after dinner, during some casual conversation, that Leon found himself cornered with a difficult question—one he knew he'd have to face sooner or later.

Ambrosini, after asking about Leon's life in Milan, asked point-blank: would he be open to a permanent move to AC Milan?

At first, Leon panicked a little.

But then he remembered Mourinho's recent phone call.

His head cleared.

In the end, Leon gave a diplomatic answer: "I have four years left on my contract with Real Madrid. If Milan and Madrid can reach an agreement, I'd have no problem with that."

Ambrosini nodded in satisfaction. Maybe he'd just asked out of curiosity, or maybe he was a mouthpiece for the higher-ups.

But to Leon, that didn't matter.

What mattered was that the manager of Real Madrid was José Mourinho—and Mourinho was his guy. That was enough.

Madrid wouldn't entertain the idea of a transfer. Leon was sure Mourinho wouldn't allow it.

As he left the restaurant that night, Leon couldn't help but glance one last time at the lights of Milan.

It really was a wonderful city.

The club, the fans, the infrastructure—everything.

But in the end, it just wasn't the right fit.

The dynasty that had once satisfied every ambitious young footballer had faded into history.

Leon turned, got into his car, and drove back to his apartment—no hesitation, no looking back.

"What a shame," he thought.

※※※

On the morning of March 1st, newspapers across Italy were plastered with images of Leon's now-iconic "mask celebration" from the Napoli match.

Leon had been the brightest star on the field in that 2-0 victory.

A goal and an assist, plus dominant play on both ends. He'd dazzled fans all over Italy with a performance that shook the league.

Handsome, hard-hitting, and despite few goals, every one of them decisive—Leon had become a star in a country that prized tough, defensive football.

And Milan? They didn't waste time.

They immediately opened talks with Real Madrid about making the loan permanent.

But that wasn't Leon's concern.

If anything unexpected came up, Mendes's people would contact him directly.

For now, he went back to doing what he always did—extra training.

After all, once the Juventus match was over, Milan would fly to London for the Champions League second leg.

Leon would get two days off, so he didn't mind burning energy now.

As long as he managed his workload well, it wouldn't affect his performance against Juve.

Not that he was underestimating them. He respected the once-mighty Bianconeri… but they weren't what they used to be.

Juventus now wasn't what they used to be. Their current strength was about on par with Palermo or Genoa—solid upper-midtable in Serie A.

A tricky opponent in the league, sure, but not a serious threat to a title-chasing AC Milan.

Allegri clearly didn't regard them as a major obstacle either. Ahead of the second leg of the Champions League Round of 16 against Spurs, he rotated several starters and sent out a backup-heavy squad to the outskirts of Turin to face Juve at the Stadio Olimpico.

This temporary home ground, used before Juventus inaugurated their new stadium, only seated around 27,000 fans. For Juve's vast local fanbase, filling the stands was never an issue.

As a result, Milan supporters only managed to secure just over 3,000 away tickets.

In the smaller, more compact stadium, the home fans' chants and cheers rang louder, creating a suffocating pressure that posed some early problems for Milan.

At least for Robinho—once again, the "Prince of the Step-Over" looked completely lost.

Was it the relentless booing from the Juventus fans that made his legs go soft? Or was it simply that he couldn't deal with his compatriot Melo?

Either way, despite controlling possession, Milan accomplished little in the first half. During the break, Allegri had seen enough and decisively replaced Robinho.

Zlatan Ibrahimović, stepping in to lead the line, finally struck up a rhythm with Cassano, who had also suffered for 45 minutes being dragged down by Robinho.

With Ibra organizing the attack from the front, Boateng and Cassano found their rhythm. Leon too was given several good chances to push forward and contribute.

Then, in the 73rd minute, Cassano rolled a pass across the top of the box. Ibra faked a shot, cut inside to wrong-foot Barzagli, and let fly the best scoring chance of the night for Milan.

Gigi Buffon had been spectacular, already denying six on-target Milan efforts. And once again, he got a hand to Zlatan's low shot, deflecting it away with a diving save.

But the rebound fell straight to Cassano, who had followed the play perfectly. The Italian forward didn't hesitate, slotting the ball into the net to give Milan a 1–0 lead in Turin.

With less than 20 minutes to play, Juve's morale took a massive hit. They'd spent the entire match trying to lock down a point—and had almost pulled it off.

They'd defended for 73 long minutes. And now, to see it all undone?

Their players were furious, but Allegri wasn't about to let the match slip.

He immediately substituted Flamini and Cassano, bringing on Boateng and Van Bommel.

With two changes, Milan morphed into a team with three, even four holding midfielders—absolutely dead set on defending the lead.

Leon and Van Bommel locked down the central midfield, forcing Juve to push wide and attempt hopeful crosses or long balls over the top.

But with Nesta and Thiago Silva in top form, Juve's aerial target, Luca Toni, barely saw the ball.

Milan ground out the final minutes, completely suffocating Juve's offense and walking away with yet another key win ahead of their Champions League clash.

The win kept Milan's streak alive and further solidified their dominance atop Serie A.

Napoli, deflated by their loss to Milan, had drawn against Brescia in the previous round, and now trailed the Rossoneri by 16 points.

Even Inter, who had won their last two matches, were still 13 points behind.

With just ten league games remaining, even if Inter went on a perfect run, Milan would only need six more wins to mathematically secure the Serie A title.

After more than six years, Milan could almost feel the Scudetto in their hands.

But before they could focus fully on finishing the job, one more mountain remained.

On March 8th, with Leon unavailable due to UEFA rules preventing him from playing for two clubs in one Champions League season, Milan's first-team squad—minus their young midfield dynamo—traveled with Allegri to London.

They were determined, this time, to make up for the defeat in the first leg against Tottenham.

On the night of March 9th, the second leg of the Champions League Round of 16 kicked off at White Hart Lane.

Tottenham set out to defend their aggregate advantage, parking the bus with a tight, organized back line.

Milan, with no other choice, attacked relentlessly.

Allegri knew that with no margin for error, all that mattered was finding a way to break down the English side's defense.

And so began a thrilling, high-tempo battle.

Milan threw everything at them: using Zlatan's hold-up play to feed Pato on inside runs, letting Cassano take defenders one-on-one from the wing, and firing off long-range shots from Boateng's late runs.

Everything Allegri could imagine, every strategy his players had practiced—they tried it.

But Spurs held firm.

Dawson was immense, leading the defense with bravery and anticipation, and Milan's first-half flurry came up empty.

In the second half, Milan threw on Inzaghi for Pato in the 52nd minute.

Redknapp responded in kind, bringing on Gareth Bale for Van der Vaart—a clear statement of intent to strike back on the counter.

That made Allegri hesitate.

Seeing Bale start to terrorize Gattuso down the left, Allegri wavered—and missed his window to adjust.

Milan, too cautious to risk it all, simply didn't have the weapons to force the issue anymore.

They were no longer a team that could trade blow for blow with the younger, faster sides of Europe.

And so the match ended 0–0. No goals, no miracles.

Milan's European campaign came to a disappointing halt.

But oddly enough, the disappointment was paired with a sense of relief.

With no more European distractions, Milan could now turn all their focus to the league and Coppa Italia.

Instead of fighting on three fronts, they now had just two. And with only three potential Cup matches remaining, the path was suddenly much clearer.

If they managed things well, a domestic double—Serie A and Coppa Italia—was still very much in reach.

Back in Italy, the players didn't dwell.

They shook off the result and immediately began preparing for their next league fixture against Bari.

They weren't thinking about Inter anymore.

All that mattered now was taking it one match at a time—and winning until the very end, until they reclaimed the Scudetto they'd been chasing for years.

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