Jean Montero – Olympiacos' Tactical Gamble: From Valencia to Piraeus

He landed at Athens International Airport "Eleftherios Venizelos" at 2:20 PM on Tuesday, carrying a black sports bag and the smile of a man who knows he is stepping into a big game. Jean Montero, 23, the Dominican point guard, had just finished international duty at the 2027 World Cup qualifiers in Qatar (August 27–September 12), flew through Madrid, then touched down in Athens. A crowd of about 300 Olympiacos fans had been waiting since 1 PM, chanting his name. But to me – a man who has followed European basketball for 36 years – this moment is not just a welcoming ceremony for a new signing. It is a tactical declaration, a test of Giorgos Bartzokas' system, and a big question about how Olympiacos will operate in the EuroLeague next season. Last season at Valencia, Montero was not just a rising star. He was the EuroLeague Rising Star, made the All-EuroLeague Second Team, won Playoffs MVP, and led Valencia to the Final Four. In the domestic ACB league, he won the championship, took Finals MVP, and also made the All-ACB Team. Those numbers do not lie: averages of 16.4 points, 5.8 assists, 3.9 rebounds per game in the EuroLeague, with a PIR of 19.7 – the highest among guards under 24. But I have learned that numbers are just a map, while the game is a storm. The question is not how good Montero is, but whether he can play in the storm called Olympiacos. Let's look at the context. Olympiacos finished third in the EuroLeague last season, losing in the semifinal to Real Madrid in a game where their offense completely stalled in the final quarter. Coach Bartzokas, known for building an offense based on constant ball movement and flexible pick-and-roll, lost Thomas Walkup – their primary playmaker – to Monaco. Adding Montero is not just a replacement; it is a philosophical shift. Walkup was a pure playmaker, prioritizing tempo control. Montero is a scorer, capable of creating his own shot off the dribble, but lacking experience in running a game at the highest level. In a brief press conference at the airport, Montero said: "I don't feel pressure from basketball, I enjoy it. I just want to be competitive." That statement sounds carefree, but to me, it holds a deeper truth. When I reviewed the tape of Montero's 12 games at Valencia last season, I noticed something: he plays best when given freedom, when the system revolves around him. At Valencia, coach Alex Mumbrú designed the entire offense to optimize Montero's one-on-one ability. He was allowed to handle the ball a lot, averaging 8.2 pick-and-rolls per game – the highest in the league. But at Olympiacos, Bartzokas does not build the system around an individual. He builds it around principles: ball movement, spacing, and reading situations. This difference could be Montero's biggest challenge. Let's compare with a similar case: in 2026, I used to think xG was nonsense, until it explained why we lost. In basketball, I have seen many talented players fail when moving from a "star" system to a "team" system. A prime example is Shane Larkin when he left Baskonia for CSKA Moscow – it took half a season to adapt. Conversely, there are players like Nemanja Nedovic, who thrived in Bartzokas' system at Crvena Zvezda, thanks to his quick decision-making and acceptance of a secondary role. Montero's strength is his ability to attack the rim and create points from difficult situations. He has a burst speed of 3.2 m/s over the first 10 meters – the fastest among EuroLeague guards last season. He can handle the ball with both hands, and his free-throw shooting at 89% is a sign of a reliable shooter. But his biggest weakness lies in defense. His defensive rating at Valencia was 112.4 – among the worst 20% in the league. He often gets caught in screens and lacks the physical weight to guard bigger guards. In a league where teams like Real Madrid or Panathinaikos have guards over 1.95m, this is a hole that can be exploited. But there is another perspective, a counter-intuitive one. Maybe Olympiacos does not need Montero to defend well. They have Sasha Vezenkov and Moustapha Fall – two of the best rim protectors in Europe – to cover for him. Bartzokas often uses a "drop coverage" scheme in pick-and-roll, which can reduce pressure on the perimeter defender. If Montero is given the primary offensive role and is surrounded by capable defenders, he could become an extremely dangerous offensive weapon. Look at how Olympiacos used Kostas Sloukas before – a scoring guard but not an excellent defender – in this system. Sloukas had the most successful seasons of his career under Bartzokas, not because he defended better, but because the system shielded him. I reviewed Montero's last 5 games in the ACB playoffs. One detail caught my attention: in the final against Real Madrid, when Valencia trailed by 10 points midway through the third quarter, Montero scored 14 consecutive points himself, bringing his team back. He did not flinch under pressure. But more importantly, it was how he read the situation: he noticed that Real Madrid's center, Walter Tavares, often dropped deep in pick-and-roll, so he started taking mid-range shots from 4-5 meters. That shows a high basketball IQ – a quality not visible in the stat sheet. However, there is a bigger concern: adapting to the pace and intensity of a 70-game EuroLeague season. Last season, Montero played only 45 games. The difference in workload is enormous. Historically, many young players have collapsed in the second part of the season due to exhaustion. I remember the case of Mario Hezonja at Barcelona – great talent, but unable to sustain form over a long season. Bartzokas, known for managing player loads, might rotate Montero wisely. But will Montero accept a bench role in some games? That is a psychological question, not a tactical one. Look at what Montero said about his coach: "I like his style. Olympiacos is one of the best teams in the EuroLeague for many years, they play the same style." This statement shows he has done his homework. But I wonder: does he truly understand that "the same style" demands personal sacrifice? Bartzokas is famous for requiring guards to move off the ball constantly, to cut, to participate in the ball rotation. Montero, accustomed to holding the ball often, may have to completely change his habits. In Valencia's first EuroLeague game last season, Montero held the ball for an average of 7.2 minutes per game – the most in the league. At Olympiacos, that number could drop to 4.5 minutes, because Vezenkov and Fall also need the ball. This is where I remember the lesson of Belgium 2026: a golden generation does not automatically produce victory. In basketball, that means assembling talented individuals does not guarantee success. Olympiacos already has a strong collective, and adding Montero could create imbalance. But there is also the opposite possibility: Montero could become the final piece that helps them break through the Final Four ceiling. Look at how they lost to Real Madrid in the semifinal last season: they scored only 68 points, 12 of which came from one-on-one situations. They lacked someone who could create their own shot in difficult moments. Montero is exactly that type of player. I spent two weeks to trust data, but it took twenty years to understand that it is still not enough. Data says Montero is one of the best offensive guards in Europe. But data cannot measure integration into a new culture, a new city, a demanding coach. I remember when I was a player, I witnessed many young talents fail because they could not handle the pressure of a big club. Olympiacos is not Valencia. Here, every loss is a crisis. Fans demand titles, not development. But there is one point that makes me optimistic. Montero has been through World Cup qualifiers with the Dominican national team, where he had to carry great responsibility. He led the team to qualify for the 2027 World Cup, averaging 22.1 points in 6 qualifying games. That shows he can perform under pressure. And he chose Olympiacos, not a smaller club, which shows his ambition. Look at the schedule: Olympiacos will open the EuroLeague on October 3 against Baskonia. That will be the first test. I will watch how Montero handles double-teams, how he reacts when substituted mid-game, and how he shares the ball with Vezenkov. If he gets through the first 10 games without signs of breakdown, I believe he could become one of the most successful signings of the season. I do not predict. I only read data and cross-check with what I see on the court. Data says Montero is a special talent. The game will tell whether he fits Olympiacos. I will wait until February, when the season is halfway through, to make a final judgment. For now, I can only say this is a fascinating gamble – one where both sides could win, or both could lose. In the Olympiacos locker room, the number 4 jersey is already hung. Montero will wear it. But that jersey does not create history by itself. The one who wears it must write his own story. And for me, that is the most interesting thing to watch in the upcoming EuroLeague season.