Todd Boehly's Attempt to Sign Cristiano Ronaldo for Chelsea

Todd Boehly pushed hard to bring Cristiano Ronaldo to Chelsea during the Portuguese star’s turbulent second spell at Manchester United, but ran straight into a brick wall named Thomas Tuchel.

According to The Athletic, Boehly flew to Portugal and sat down with super-agent Jorge Mendes, leaving the meeting highly enthusiastic about the prospect of Ronaldo in blue. At that point, Ronaldo was deeply unsettled at Old Trafford and looking for a way out, long before his eventual move to Al-Nassr in Saudi Arabia.

Boehly liked the idea. Tuchel did not.

The then-Chelsea head coach repeatedly made his opposition to signing Ronaldo crystal clear. For Tuchel, the 37-year-old forward did not fit his tactical vision or the pressing structure he demanded from his front line. The clash in viewpoints added to a growing tension between owner and manager during that first chaotic summer of the new regime at Stamford Bridge.

That summer window had already frustrated Boehly. Chelsea failed in attempts to land several of Tuchel’s key targets: Matthijs de Ligt, Raphinha, Frenkie de Jong and Presnel Kimpembe all slipped away. Each miss added to the strain.

Raheem Sterling was different. That deal caused far less internal debate. Boehly personally drove the negotiations with Manchester City, eventually securing the England international for £47.5 million. It was one of the first marquee signings of the new era and one Boehly could point to as a success.

But the wider strategy behind those moves came under scrutiny quickly, not least from Boehly himself. Speaking at an event in February, he openly admitted how raw and improvised his approach had been when he stepped into the interim sporting director role.

“I found myself stuck in the interim sporting director role over the summer, without knowing what makes a footballer good,” he said. “But I knew that if Manchester City wanted Marc Cucurella, then I wanted him. It was as simple as that.”

It was a blunt confession from the man fronting one of Europe’s biggest clubs, and it underlined how improvised that first transfer window really was — from chasing Ronaldo to reacting to rival interest in Cucurella.

By January 2023, Boehly had stepped away from the interim sporting director position, with Chelsea moving to install a more traditional football structure behind the scenes.