Roma agreed terms with Stuttgart and prepared a private jet to bring Jamie Leweling to Italy, but the winger’s repeated doubts ultimately caused one of Deadline Day’s most dramatic transfers to collapse.
Roma appeared to be on the verge of securing the attacking reinforcement Gian Piero Gasperini had requested.
An agreement had effectively been reached with Stuttgart, a private aircraft was prepared to travel to Germany and optimism grew that Jamie Leweling would become Roma’s final signing of the summer transfer window.
The situation changed dramatically as the deadline approached. Leweling reconsidered the move, the flight was initially postponed and later cancelled, leaving Roma without sufficient time to complete the transfer.
Roma Agreed €35m Package With Stuttgart
Roma reportedly offered a package worth approximately €35 million and reached an agreement with Stuttgart over the terms of a permanent transfer.
The remaining obstacle was obtaining Leweling’s definitive approval.
The German international initially opened the door to joining Roma, leading the Giallorossi to believe the operation could be completed. However, he continued to alternate between accepting the transfer and remaining with Stuttgart throughout Deadline Day.
Tony D’Amico later confirmed that the Leweling agreement was in place before the player changed his mind.
“The Leweling deal was agreed with Stuttgart and the player, but he had second thoughts, so we stopped,” the Roma sporting director explained.
Friedkins Prepared Private Jet for Leweling
Roma progressed far enough with the operation to arrange a private jet associated with the Friedkin ownership.
The aircraft was expected to travel to Stuttgart and immediately bring Leweling to the Italian capital, allowing him to undergo his medical examinations, sign his contract and complete the registration process before the transfer deadline.
However, the plane never departed.
Leweling and his representatives reportedly renewed their doubts at the decisive moment. The indications that had previously encouraged Roma were never converted into the final authorization required to proceed.
As time continued to pass, the possibility of completing the medical and documentation became increasingly remote. The flight was eventually cancelled and Leweling decided to remain in Germany.
Everton Reportedly Entered the Leweling Race
Another unusual element emerged during the negotiations when Everton reportedly entered the race for Leweling.
The Premier League club, which is also owned by the Friedkin family, approached the winger while Roma were attempting to complete their own agreement with Stuttgart.
Everton reportedly presented a package worth €43 million including bonuses, but Leweling also rejected the opportunity to move to England.
The involvement of another Friedkin-owned club added another unexpected twist to a transfer saga that had already changed direction several times.
Roma Left Without Time to Secure an Alternative
Roma’s confidence that Leweling could eventually approve the move kept negotiations alive until the final hours of the window.
That uncertainty also reduced the time available for the club to pursue another attacker. The Giallorossi had previously established the conditions of a deal for Luiz Henrique, but technical complications prevented the operation with Zenit Saint Petersburg from being completed.
A final attempt to secure Jamie Bynoe-Gittens also failed because Chelsea remained unwilling to sanction the winger’s departure under Roma’s preferred formula.
With no alternative considered sufficiently convincing, Roma decided against signing another player simply to fill the position.
Cancelled Flight Symbolizes Roma’s Deadline Day
The private jet that remained grounded became the defining image of Roma’s frustrating final day of the summer market.
Gasperini had publicly requested another wide attacker, while Roma identified Leweling as the player capable of completing the squad. The agreement with Stuttgart was ready, the logistical arrangements had been made and the club pushed until the final possible hours.
Leweling’s hesitation ultimately proved decisive. By the time another opening reportedly arrived, the technical window for completing his flight, medical examinations and registration had become too narrow.
Roma’s renewed push for Leweling therefore ended without an agreement, leaving the German international at Stuttgart and Gasperini one attacker short.
Sources: La Repubblica, La Gazzetta dello Sport, Corriere della Sera
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