Xabi Alonso could be set to repeat a costly error involving Michael Olise’s brother before officially taking charge at Chelsea.
The Spaniard is due to begin his tenure at Stamford Bridge on July 1, having penned a four year deal. The former Liverpool star managed Real Madrid and Bayer Leverkusen before joining the Blues, giving him a wealth of experience in transfer decisions.
But he may be making a significant blunder by allowing Richard Olise to depart when his contract expires.
The younger Olise
The younger Olise brother spent a decade in the Chelsea academy without making a first team appearance. He did earn a place on the bench during Chelsea’s 3-1 victory over Astana in the Conference League in 2024/25, which entitled him to a winner’s medal when the Blues lifted the trophy.
The 21 year old will now move on as a free agent. While no clubs have been publicly linked with the defender as yet, by letting him walk out the door at such a tender age, Chelsea risk repeating the same mistake they made with his brother Michael.
History repeating?
The elder Olise sibling endured a similar experience back in 2014 when he was released by Chelsea as a youngster after spending seven years in the academy without breaking through to the first team. The then 14 year old moved to Manchester City’s youth set up before joining Reading, where he made his senior bow at 17.
Chelsea would come to rue their decision to part ways with Olise, as he has grown into one of Europe’s most coveted talents. The winger joined Crystal Palace in 2021 and began a meteoric rise.
The France international registered 41 goal contributions across 90 appearances for the Eagles before sealing a £50.8m switch to Bayern Munich. Olise is now a two time German champion, having recently claimed Player of the Season honours.
He stands among the frontrunners for the Golden Ball at the World Cup. He has racked up 96 goal contributions in 107 outings for Bayern and also rejected the chance to return to Chelsea in 2023.
The pattern
While Richard operates in a different position to his brother, featuring at either left or right back, he may emulate his brother by carving out a stellar career after departing west London.
Only time will tell whether he can match his sibling’s career path. But Alonso could be left regretting his error if he comes anywhere close to replicating the Bayern star’s trajectory.
The bottom line
Chelsea let Michael Olise go at 14. He became a superstar at Bayern Munich. Now they’re letting his brother Richard walk for free at 21.
Alonso hasn’t even officially started yet, and he’s already making a decision that could come back to haunt him.
Richard may never reach Michael’s level. But he might. And if he does, Chelsea will have made the same mistake twice.
A decade in the academy. No first team minutes. A free transfer out the door.
History doesn’t always repeat itself. But sometimes it rhymes. And Chelsea fans will be watching Richard Olise’s next move very carefully.
