Former Chelsea, Arsenal and Manchester City winger Raheem Sterling has unexpectedly been linked with a move to Tottenham Hotspur, with ex-Spurs midfielder Jamie O’Hara urging the club to take a low-risk punt on the experienced forward.
Sterling became a free agent earlier this week after Chelsea confirmed his contract had been terminated by mutual consent, bringing an end to a mixed three-and-a-half-year spell at Stamford Bridge following his high-profile switch from Manchester City in 2022.
He arrived in west London as one of Chelsea’s headline signings, fresh off multiple Premier League titles under Pep Guardiola and expected to play a central role in the club’s rebuild. While the England international produced moments of quality, his time at Chelsea was undermined by inconsistency, frequent managerial changes and constant squad upheaval.
In announcing his departure, Chelsea thanked Sterling for his contribution and wished him well in the next chapter of his career.
Last season, Sterling attempted to reignite his form with a loan move to Arsenal, hoping for regular minutes under Mikel Arteta. However, opportunities were limited. Despite making 27 appearances across all competitions, he started just seven league games and was often used from the bench, leading Arsenal to pass on a permanent deal.
He subsequently returned to Chelsea but was deemed surplus to requirements under Enzo Maresca, becoming one of several senior players frozen out as the squad was overhauled. As a result, Sterling has spent almost eight months without competitive football, a stark contrast to his previous career at the top end of the Premier League and Champions League.
Now 30, Sterling faces a pivotal decision over his future, weighing up a potential move abroad against the chance to re-establish himself in England. Jamie O’Hara believes a Premier League return—specifically with Tottenham—would make sense.
Speaking on talkSPORT, O’Hara said Spurs should seriously consider signing Sterling, arguing he would add quality and experience to their wide options. He suggested a short-term deal until the end of the season would minimise risk for Tottenham while giving the player a chance to prove himself.
O’Hara also dismissed doubts over Sterling’s motivation, pointing out that the winger chose to leave Chelsea to play football rather than sit on the sidelines. He believes that shows a continued hunger to compete at the highest level.
According to O’Hara, Tottenham’s need for a left winger, combined with Sterling’s availability on a free transfer, makes the move a sensible gamble. He added that with the right environment and renewed confidence, Sterling could still deliver decisive moments, drawing on his proven track record at Liverpool and Manchester City.
From Spurs’ perspective, the idea carries appeal. Injuries and a demanding schedule have exposed a lack of consistency on the left flank, and Sterling’s pace, movement and big-game experience could offer valuable depth, either as a starter or impact substitute.
A move would also add another twist to Sterling’s London journey after spells with Chelsea and Arsenal, giving him the chance to prove he still belongs among the Premier League’s elite. While no formal approach has been made, O’Hara’s comments have sparked debate among supporters over the balance between risk and reward.
For Sterling, the objective is simple: regular football, restored confidence and a platform to showcase his ability once more. Whether that opportunity comes at Tottenham remains uncertain, but the possibility of a north London revival is now firmly on the table.
