Over more than a decade at Liverpool, Manchester City and Chelsea, Sterling has now reached a point where the doors at England’s elite clubs are closing.
With two weeks left in the transfer window, he finds himself searching for an escape route that keeps him relevant.
It is a familiar scenario. Twelve months ago Chelsea had already decided he was surplus to requirements, and only a surprise late loan to Arsenal offered him a lifeline. Sterling spoke with real optimism about reigniting his form at the Emirates, keen to prove he was not finished at the top level.
The reality was stark. Just seven league starts, no Premier League goals, and two assists. His only strike came in the Carabao Cup against Bolton. Arsenal never considered making his stay permanent and Chelsea have no interest in reintegrating him.
So where does that leave him now?
The work to find Sterling a new home has already started and they want it sorted before deadline day. His preference is to stay in London for family reasons and sources suggest Fulham, Crystal Palace and West Ham as realistic options.
All three clubs are monitoring the situation, but none are yet convinced about the investment. His £300,000-a-week wages remain a huge factor, and any deal will hinge on how much Chelsea are prepared to subsidise.
There are other concerns too. After a barren year, clubs want to be sure they are not signing a player going through the motions.
Yet those close to Sterling insist his professionalism is intact and that he has a desire to prove he is far from washed up.
The foreign offers have been there, but he is not rushing towards them. At 30, with young children settled in England, Sterling is prioritising stability as much as status.
That probably now means dipping below the Champions League level he has known since his teenage breakthrough.
He has two years remaining on his contract but is training outside of the main group at Chelsea, waiting for his next club.
Now, the question is less about what he has achieved - 13 years at the highest level, countless trophies, 82 England caps - and more about what he has left.
Sterling still sees himself as a top player. Over the next fortnight, we will find out who believes him.
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