Three big questions: Chelsea’s Ross Barkley and hesitation

LONDON, ENGLAND - JANUARY 11: Frank Lampard, Manager of Chelsea embraces Ross Barkley of Chelsea after their sides victory in the Premier League match between Chelsea FC and Burnley FC at Stamford Bridge on January 11, 2020 in London, United Kingdom. (Photo by Mike Hewitt/Getty Images)
LONDON, ENGLAND - JANUARY 11: Frank Lampard, Manager of Chelsea embraces Ross Barkley of Chelsea after their sides victory in the Premier League match between Chelsea FC and Burnley FC at Stamford Bridge on January 11, 2020 in London, United Kingdom. (Photo by Mike Hewitt/Getty Images) /
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Chelsea’s English midfielder Ross Barkley celebrates after scoring the opening goal of the English FA Cup quarter-final football match between Leicester City and Chelsea at King Power Stadium in Leicester, central England on June 28, 2020. (Photo by Tim Keeton / POOL / AFP) / RESTRICTED TO EDITORIAL USE. No use with unauthorized audio, video, data, fixture lists, club/league logos or ‘live’ services. Online in-match use limited to 120 images. An additional 40 images may be used in extra time. No video emulation. Social media in-match use limited to 120 images. An additional 40 images may be used in extra time. No use in betting publications, games or single club/league/player publications. / (Photo by TIM KEETON/POOL/AFP via Getty Images)
Chelsea’s English midfielder Ross Barkley celebrates after scoring the opening goal of the English FA Cup quarter-final football match between Leicester City and Chelsea at King Power Stadium in Leicester, central England on June 28, 2020. (Photo by Tim Keeton / POOL / AFP) / RESTRICTED TO EDITORIAL USE. No use with unauthorized audio, video, data, fixture lists, club/league logos or ‘live’ services. Online in-match use limited to 120 images. An additional 40 images may be used in extra time. No video emulation. Social media in-match use limited to 120 images. An additional 40 images may be used in extra time. No use in betting publications, games or single club/league/player publications. / (Photo by TIM KEETON/POOL/AFP via Getty Images) /

2. Will Chelsea regret selling him if he goes?

Barkley was bought by Chelsea in part because his fee was ridiculously low and in part because of the potential he possessed. The English midfielder was never a clear super star in the making, but there was a sense that the right environment could bring him very close to being one.

That has not quite happened at Chelsea but it is hard to deny that there have not been flashes. When Barkley is able to play freely, with seemingly as little instruction as possible, he tends to do phenomenally. When it is clear that he is heavily instructed and has to stick to a certain way, he looks burdened. Overthinking becomes overplaying becomes poor form.

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If Chelsea was to sell Barkley, they would surely make a tidy profit. But depending on which club he went to, it may only be a matter of time before the Blues begin to regret it.

Barkley has everything he needs to not only be a good Premier League player, but a great one. It is just a matter of the right set up that allows him the freedom he needs to do his thing. At Chelsea that has come and gone, but at another club where it is present week in and week out, Barkley could turn into a star.

The Blues, regardless of what they sold him at, may then regret that sale. It wouldn’t mean that it would have worked at Chelsea, but seeing him succeed elsewhere would certainly make one wonder.