Cristiano Ronaldo was reportedly close to joining Chelsea during his second stint at Manchester United between 2021 and 2023. In 2022, Chelsea owner Todd Boehly met with Jorge Mendes, Ronaldo's agent, to discuss a potential transfer. Boehly was attracted to the idea of bringing the Portuguese forward to Stamford Bridge, especially as Ronaldo was experiencing a turbulent period at Manchester United, which had finished sixth in the Premier League. However, the proposed move was ultimately blocked by then-Chelsea manager Thomas Tuchel. According to 'The Athletic', Tuchel expressed firm opposition to signing Ronaldo on multiple occasions, effectively shutting down the deal. Consequently, Ronaldo remained at Old Trafford until his departure in 2023, eventually moving to Al-Nassr. Chelsea, despite its owner's interest, did not pursue the transfer further due to Tuchel's stance.