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Roma avoided losing Manu Kone to Chelsea on 1 September after head coach Gian Piero Gasperini intervened to stop the deal. Chelsea had approached the Friedkins directly with an offer worth €60 million plus a loan with an option to buy for winger Jamie Bynoe-Gittens, a player Gasperini had strongly sought. A meeting to finalise the transfer was scheduled for 12pm Italian time before Gasperini learned of the negotiations and moved to block it. Gasperini had expressed his determination to keep Kone only the previous evening, viewing the midfielder as essential to his plans. Kone impressed in Roma's recent match against Lecce on Monday. When the coach discovered the Chelsea talks, he contacted sporting director Tony D'Amico and together they escalated the issue to the Friedkins, causing the deal to stall and ultimately collapse. Roma had already begun exploring alternatives, with AC Milan's Youssouf Fofana identified as a potential replacement. Retaining Kone strengthens Roma's position as they aim to mount a title charge. Losing the France international at such a critical moment in the season would have damaged momentum—a particularly serious concern given Gasperini's reputation for strong reactions when matters do not develop to his satisfaction.

Jamie Leweling has rejected Roma's advances and chosen to remain at Stuttgart, ending the club's last-ditch attempt to complete a transfer before the 20:00 deadline on 1 September. The German winger, 25, turned down Roma's improved offer of €30 million fixed plus €5 million in bonuses, as well as proposals from other clubs including Everton, according to Sky Sport Deutschland's Florian Plettenberg. Roma had accelerated their pursuit over the previous day and appeared close to closing the deal after agreeing terms with Stuttgart. Head coach Gian Piero Gasperini had specifically requested two reinforcements before the transfer window closed, but the move now looks to have failed at the final hurdle. A private jet had been prepared and positioned in Stuttgart to transport Leweling to Rome once an agreement was reached, but the player requested time to consider his future and ultimately decided against the move. Evan Everton made a concrete proposal in the night as well, but the 2001-born winger opted to continue his career in the Bundesliga. Throughout the day, reports from Fabrizio Romano and Gianluca Di Marzio indicated that Leweling had begun to open the door to a transfer and was even summoned to Stuttgart's offices on the morning of 1 September after training. However, as the final hours of the window ticked away, his decision to stay became clear, leaving Roma without the attacking reinforcement Gasperini had sought.

Roma's pursuit of Leweling ended in failure on the final day of the transfer window. Gianluigi D'Amico, the club's negotiator, had intensified efforts for the German winger in recent days, viewing him as the perfect profile for a Roma squad targeting the Serie A title. The deal appeared to be progressing well until Leweling himself applied the brakes, his initial refusal to move to the capital cooling negotiations. On 1 September, however, Roma reopened everything. The club raised its offer to €30 million plus €5 million in bonuses and, according to Sky Sport, secured Leweling's openness to a transfer to the capital. Roma believed in the move and committed fully to closing it before the 20:00 window deadline. To underline their intent, the club chartered an aircraft to transport Leweling to Ciampino airport, with departure scheduled for 16:00 from Stuttgart. The plan was in motion—until it abruptly was not. The flight was cancelled, and from that moment everything unravelled. The negotiation cooled completely and ultimately collapsed. There were no longer the technical procedures available to complete the operation. Leweling will not be Gasperini's new left-winger. Roma tried until the last moment, raised their offer, secured the player's willingness to move, and gave everything. But it was not enough. The transfer window closed without that final push, without the left-sided attacker the head coach had pursued until the very end.