Anonymity, ascent, stardom and combustion: Theo Hernandez’s AC Milan journey

Theo Hernandez’s time at AC Milan has come to an end after six years, and a lot of the time in football endings don’t go the way you hoped.

Theo’s over half-decade spell in the red and black was brought to a close as his permanent move to Al-Hilal was confirmed by both clubs. Having arrived at Milan from Real Madrid in the 2019 summer transfer window, he amassed 262 appearances, 34 goals and 45 assists.

He was a key part of the side that won the Scudetto in 2021-22 under Stefano Pioli, then reached the semi-finals of the Champions League the following season. He also lifted the Supercoppa Italiana last season too, so how did we get to the point of such a bitter exit?

Bright beginnings

Theo arrived as a bright-eyed boy in the 2019 summer transfer window from Real Madrid, and he was initially expected to slot straight in as the starting left-back, despite an element of mystery surrounding his signing.

There was the usual chatter around the Frenchman: Real rated him highly and would rather not lose him, but there were some ‘attitude problems’ that forced them to reflect. From here, a special relationship with Paolo Maldini was born.

It is believed that Bayer Leverkusen were also very keen on signing him, so Maldini – then working as the technical director of the Rossoneri – hopped on a plane to Ibiza for a one-on-one discussion about the idea of joining Milan.

Theo instantly fell in love with the idea that a legend like Maldini had come to visit him specifically to pitch the project, while Paolo completed one of the most important purchases of his time and for just €20m.

Image: acmilan.com

It did not all go perfectly right from day one, however. Ricardo Rodriguez started the season as the established left-back under Marco Giampaolo in a back four, with the then-coach preferring what he perceived to be a more experienced and solid presence.

Nonetheless, Hernandez made his debut on 21 September, playing 18 minutes in a 2–0 defeat against Inter. There were some bright sparks initially and his playing time increased more and more, to the point where he overthrow Rodriguez, and cemented his spot when Stefano Pioli arrived.

On 5 October he scored his first goal for the club in a 2-1 comeback win away at Genoa, and he never looked back from there. In his first season – despite not being a starter for a decent portion – he amassed seven goals in all competitions and had three assists.

Looking back, though, it would still be fair to say Theo was far from the finished product in that debut 2019-20 season. There was a lot of chaos going on around him of course, but his defensive ability was being scrutinised.

After the lockdown period few knew which direction things would take, especially amid rumours that Ralf Rangnick’s arrival as an all-encompassing head coach, manager and director role was imminent. In the end Pioli stayed, and ‘the TGV’ kept speeding on.

Among the most memorable moments from his first two season, one stands out on 23 December 2020 when his 93rd-minute winning goal – a header from a corner – gave Milan a victory over Lazio to keep them top of Serie A.

In that 2020-21 campaign, Milan emerged out of nowhere to be Scudetto contenders and though they eventually fell short to Antonio Conte’s Inter, Hernandez was showing himself to be the best in the league in his position. He ended it with eight goals and seven assists in all competitions.

Established stardom

The signs were there going into the 2021-22 season that Milan could really kick on and not just fight for the title again, but actually go and win it. Pioli was building a group that prided itself on togetherness and it was full of game-breakers too, of which Theo was one.

At this point, it feels right to mention that Theo Hernandez had struck up an excellent relationship with Rafael Leao on the left flank. The pair had even coined the nickname ‘Theao’, and many believed it to be the most devastating full-back/winger tandem in Italy, if not in Europe.

In this, the Frenchman’s own role was evolving into something more than being a swashbuckling extra winger. He was beginning to assume more responsibility, wearing the captain’s armband for the first time during a game against Roma in January 2022.

It felt like a full-circle moment and only two-and-a-half years into his time at Milan. Having been signed by perhaps the most iconic ‘capitano’ in the history of the club, and certainly the most successful, Maldini must have had a gleam in his eye seeing his protégé climb so rapidly.

Three days after he wore the armband, the then-24-year-old scored a brace in a 3-0 win against Venezia, becoming first defender to score at least three braces in Milan’s Serie A history. Suddenly, he was beginning to close in on Maldini’s goal record.

As Milan powered on in the battle for the Scudetto, Theo perhaps reached a peak of sorts, following that excellent month of January by signing a long-term contract extension until 2026 in February. It was a fitting reward for a player that, by now, was worth at least triple what he was signed for.

Then came the crowning moment, on 15 May 2022. With Milan holding onto a tentative 1-0 lead against Atalanta in the penultimate round of the season, Hernandez officially ran for 95 metres from box-to-box, providing a composed finish at the end of it to make San Siro explode.

That goal was not only his best for the club in the eyes of many, but by far his most significant. One week later, Milan lifted their 19th Scudetto after a 3-0 win away against Sassuolo, beating their rivals Inter to get revenge. Theo registered five goals and six assists, the most for any defender in Serie A that season.

The following season would not be as successful in the league with Napoli being the runaway winners, but the former Atletico Madrid man began to write a story in the Champions League, as the team around him did.

As part of a run to the semi-finals, he had a big hand in the only goal of the tie against Spurs, then drawing a red card from Cristian Romero in the return leg amid an outstanding collective defensive effort.

Then, in the semi-final against Napoli, he was asked to do more of a defensive job. The defender passed the test with flying colours, keeping Hirving Lozano quiet in leg one and Matteo Politano in check during the second leg, allowing Leao to gallop forward and, well, we know the rest.

The decline and legacy

If you ask some sections of the Italian media and the Milan fan base, they might tell you that Theo Hernandez’s descent began in the 2023-24 season, when Inter ran away with the title to get the second star first.

Nonetheless, there we some positive moments that season, for example when he assisted the winning goal scored by Olivier Giroud in the Champions League game at San Siro against Paris Saint-Germain. That win looks even better now, seeing what PSG have become under Luis Enrique.

In December 2023, Pioli was battling an injury crisis with all but one of his central defenders out, so Hernandez volunteered to play as a centre-back for the first time in his senior career. He did it for a few games in the end, and it would be fair to say the tribute to his brother Lucas (a centre-back by trade) was successful.

What cannot be denied though is that 2024-25 was a nightmare for Theo Hernandez, and this is where everything began to turn a bit sour.

The image of Theo and Leao stood on the other side of the field in an away game against Lazio, while the new coach Paulo Fonseca gave important instructions to the rest of the team after a goal, became known as the ‘cooling break saga’. It would be the least controversial of the controversies, in the end.

Theo’s 27th birthday weekend ended up being probably his darkest moment with the Rossoneri, and it all happened at the Stadio Artemio Franchi as he made three colossal errors in judgement, all at a time when there were rumours of big salary demands to renew.

Firstly, the Frenchman gave away a penalty that appeared soft but it was also avoidable (he was on the edge of the area, not two steps away from goal). Then he missed a penalty at the other end, taking on a responsibility that should not have been his, as Fonseca made clear after the game.

Theo took the ball from Alvaro Morata, even though Christian Pulisic should have been the taker, and failed to beat Davide De Gea. Fonseca clarified at half-time to the players that Pulisic was the spot kick taker, yet in the second half the captain stood and watched as Tammy Abraham robbed – and missed – another penalty.

In the second half, Hernandez risked giving away a second penalty with a risky high tackle on Andrea Colpani. This time the VAR check acquitted him, but the red mist descended at full-time to end his birthday in the worst way, as he got sent off for firing a barrage of abuse at the referee Luca Pairetto.

Instead of leading by example, Theo had become an example of what not to do. This further manifested itself in the second leg of the Champions League play-off round tie against Feyenoord, when he got a red card.

What’s worse is it was for two yellow cards inside the first half, and after Milan had levelled the tie. The first was for a challenge he didn’t need to make in defensive transition; the second was for an obvious dive inside the box.

The result? The Rossoneri were eliminated by a very young Dutch side who had 10 injuries and were in chaos having just sacked their head coach. From an economic perspective, €11m for last 16 qualification went up in smoke, and Theo had to wear some of that on his shoulders.

The club decided to fine him for leaving his team-mates numerically inferior and ultimately costing them a spot in the competition. Finally, the reports began to surface that Milan were going to give up on the left-back, given that his on-field antics were no longer worth battling hard over a renewal for.

Image: Goal.com

Things drifted towards an inevitable conclusion, which was that Theo no longer had a place at Milan. So we arrive at the present day, and – after the move to Al-Hilal became official – one final parting shot was sent in the goodbye message.

“I have always known where I wanted to be, and AC Milan has always been my priority. But, unfortunately, not everything depends on one person. The direction the club has taken and some recent decisions do not reflect the values ​​or ambition that brought me here,” Hernandez said.

What exactly he is referring to, only he knows. However, after such a difficult and at times disastrous season for all of the reasons mentioned above, it has certainly rubbed some supporters up the wrong way, and the Milan hierarchy too.

The talk of directions and decisions, values and ambitions feels hollow when Theo himself failed to fully honour and respect the badge in his closing year. There are mitigating circumstances, such as never having a proper deputy and a constant circus at management level, but others managed to at least be professional every week.

It has also been suggested that Maldini’s departure is what began the slippery slope towards the present day. There is no doubting it will have had an impact given that he was a mentor-like figure, but also taking on a leadership role after a settling-in period should negate the need for any hand-holding.

Still, when a great of Milan’s modern era says that the club he is leaving is not the one that he joined, we should probably take note. The problem is, for Theo, that he was contributing to that rather than fixing it. After being left feeling deserted, a future in the desert awaits.