Todd Boehly's Attempt to Sign Cristiano Ronaldo for Chelsea

Todd Boehly tried to pull off one of the most explosive signings in recent Premier League history: bringing Cristiano Ronaldo to Chelsea.

During Ronaldo’s turbulent second spell at Manchester United, before his move to Al-Nassr in Saudi Arabia, the then-Chelsea owner held talks with super-agent Jorge Mendes in Portugal, according to The Athletic. Boehly left that meeting captivated by the idea of Ronaldo in blue.

Ronaldo’s frustration at Old Trafford at the time was no secret. The relationship with United had soured, his role had shrunk, and the prospect of a dramatic switch to a direct rival carried all the ingredients of a modern football saga.

Inside Chelsea, though, one figure stood firmly in the way.

Thomas Tuchel, the head coach then, repeatedly made it clear he did not want Ronaldo. The German pushed back strongly against any move for the Portuguese forward, cutting across Boehly’s ambition and setting the tone for a growing tension between the coach and the new ownership.

That friction did not start and end with Ronaldo. Boehly’s early transfer window, as interim sporting director, brought a string of near-misses. Chelsea failed to land Matthijs de Ligt, Raphinha, Frenkie de Jong and Presnel Kimpembe, all targets that would have underlined the new regime’s intent. Each one slipped away.

Raheem Sterling was different. There, Boehly got his man. He personally drove the negotiations with Manchester City, eventually sealing a £47.5 million deal. It was one of the first marquee signings of the new era and, crucially, one that did not ignite the same internal debate as Ronaldo.

Months later, Boehly publicly reflected on that chaotic first summer in charge and his own role in it. Speaking at an event in February, he admitted the approach behind the scenes lacked structure.

“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 candid snapshot of a learning-on-the-job operation at one of the world’s biggest clubs.

By January 2023, Boehly had stepped away from the interim sporting director position. The Ronaldo deal never happened, Tuchel had gone, and Chelsea’s recruitment strategy was already moving into another new phase.