Chelsea’s recruitment direction looks set to shift with Mauricio Alonso thought to have increased sway after a sporting-director structure that presided over a 10th-place Premier League finish last season. An incoming coach will likely prioritize left-back options that fit his preferred patterns, blending ball progression with defensive reliability.

Myles Lewis-Skelly is exactly the type of versatile, silky, ball-centric player that would suit Alonso. Chelsea also have a history of poaching Arsenal’s homegrown left-back talents. However, any deal would be costly given the teenager’s lengthy contract and Arsenal’s apparent reluctance to part ways.

“La minestra riscaldata non è mai buona, reheated soup never tastes as good.” Still, a return could appeal if presented as a clearer pathway than the one Lewis Hall currently faces at Newcastle United. Hall left west London for the north east in 2023 and has blossomed into a well-rounded defender who offers creativity and solidity. Newcastle, as a collective, have not mirrored Hall’s rise and managed to finish even lower than Chelsea last term. It remains to be seen if Alonso would want to tempt Hall back south, but he wouldn’t be the first gem Chelsea bought back after initially letting go.

Antonee Robinson presents a different profile. During the 2024–25 season, he became the first Fulham player to ever register 10 Premier League assists in a single campaign. The tireless force of nature was just as productive defensively, earning links to some of the division’s elite. Robinson hasn’t created a top-flight goal for any teammate since February 2025. Knee surgery last summer derailed his start to the 2025–26 campaign, which largely served as a setting for the U.S. international to work his way back to full health ahead of a home World Cup. Now fit and firing once again, Robinson’s stock is back on the rise and Manchester United are reportedly sniffing around. At 28, he is older than the talents Chelsea have typically targeted under BlueCo, but some experience could be valuable for a squad that has struggled with excessive youth.

Less than two years ago, Arsène Kouassi was playing in France’s third tier. The 22-year-old took Ligue 1 by storm last season, operating chiefly as a wingback in Lorient’s 3-4-2-1. Kouassi racked up six assists, a tally bettered by only one other defender in the French top flight. If Alonso experiments with a back-three, Kouassi could be an ideal outlet down the left.

Marc Cucurella has confirmed he has already spoken with incoming Chelsea manager Xabi Alonso and described the conversation as confidence building. The defender, who has been linked with both Barcelona and Atlético Madrid and has expressed interest in returning to Spain, nevertheless suggested Alonso’s message left a clear opening for continued life at Stamford Bridge.

Asked by MARCA for his feelings towards Alonso’s project, Cucurella revealed: “I’ve spoken with him and he inspired a lot of confidence in me. I’ve also spoken with [Alejandro] Grimaldo and Borja [Iglesias], who have worked with him, and they spoke very highly of him.

“The project seems very interesting.”

Cucurella has regularly been central to whichever tactical plan his Chelsea managers have chosen. Under Maresca he often operated as an inverted attacking midfielder, encouraged to get involved in central attacks while still expected to defend his left wing. That hybrid usage has been a defining feature of his time at the club.

How Alonso uses Cucurella will depend on the formation he selects. Alonso’s 3-4-3 at Bayer Leverkusen turned Grimaldo, Cucurella’s Spain teammate, into one of the deadliest wing backs in Europe, a season that produced 12 goals and 20 assists in 2023–24. By contrast, Alonso’s spells at Real Madrid tended to favour 4-3-3 or 4-2-3-1 systems, both of which call for a more traditional left back.

Cucurella’s ability to perform as both an advanced inverted midfielder and as a traditional left back gives him flexibility that could suit multiple Alonso systems. That tactical versatility, combined with the positive endorsement from figures who have worked with Alonso, frames the defender’s situation: interest from Spain remains, but a convincing conversation with the new Chelsea coach has left the option of staying at the club very much alive.

Every four years the World Cup offers a stage for players to reshape career trajectories and Nicolas Jackson arrives in 2026 needing one of those moments. The returning Chelsea loanee has seen a campaign of mixed returns: eight Bundesliga goals, half of them scored in the final five weeks of the season, and only 15 starts across the Bundesliga and Champions League compared with the 40 starts set out in his loan agreement.

That limited game time and intermittent productivity have left Jackson’s future at Chelsea unresolved. The tournament in Qatar could provide a platform to press his case to new Chelsea manager Xabi Alonso or to attract interest elsewhere. Instead he has added another question mark.

Discipline has been a recurring issue. Late in 2024–25 Jackson received a red card 35 minutes into a costly Blues defeat against Newcastle United. He was sent off again two games into that year’s Club World Cup and barely featured afterwards, an episode that may have sealed his Chelsea fate in the eyes of then manager Enzo Maresca. This past season he missed two Bayern matches because of a red-card suspension precisely when he was being given opportunities to start.

In Senegal’s World Cup warmup friendly against Saudi Arabia this week, a 0–0 draw, Jackson was shown two quickfire yellow cards which equalled a red. The 24-year-old will not be forced to miss World Cup matches by that suspension, which will instead carry over to Senegal’s next friendly, but the manner of the dismissal is unhelpful. Recklessness and immaturity to be sent off in that way risk undermining the case he needs to make on the biggest stage.

Jackson’s situation is simple in its complexity: he needs minutes and impact, not interruptions. The World Cup remains available as an opportunity, but the red card in the warmup has made an already delicate reintegration at Chelsea more difficult and left his club future in limbo.