The former Foxes frontman accepts that Champions League football will be required in order for prized assets to be kept at the King Power Stadium
Frank Lampard has already pushed through deals for Hakim Ziyech and Timo Werner, with Bayer Leverkusen playmaker Kai Havertz another of those said to figure on his wish list.
An official approach for Chilwell could be made over the coming weeks, with Phillips conceding that the “big boys” are likely to be mulling over moves for the 23-year-old defender.
Leicester are reluctant to part with any prized assets, but the outcome of a meeting with Manchester United on Sunday could be decisive – with a top-four finish on the line there.
Former Foxes striker and coach Phillips told talkSPORT of the interest being shown in Chilwell, with Chelsea seemingly leading the chase: “He was there as a youngster when we were there and we were monitoring him very closely and making sure he was being managed right, as we knew we had a gem on our hands.
“But, also, it has to come from the player; you have to listen, develop and have to live your life right and he certainly does that. He’s a very humble guy, very quiet but an awesome left-back.
“If Leicester weren’t to secure a top-four finish this season, I wouldn’t be surprised if one of the big boys come in and pay big money for him, because he’d certainly fit in to any of those top-three or top-four sides. Credit to the player but also you have to give big credit to Brendan Rodgers for bringing him on as well.”
Leicester have spent much of the 2019-20 campaign inside the Champions League spots, only to endure a wobble since the Premier League re-start in mid-June, but Phillips says missing out on elite European competition would not write off their season.
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He added: “Is it a failure? I’m not sure it would be a failure. They’d be very disappointed, of course.
“It’s not just them but other clubs have done [the same], but there’s been other clubs who have come back and performed even better, i.e Manchester United and Chelsea look really strong.
“I think they’ll be very disappointed. In a way, you could say it would be a failure but let’s not forget it is Manchester United and Chelsea and when you look at their squads player for player, I wouldn’t say they are far superior, but they’ve got two stronger squads than Leicester. It’s still not dead and buried but I think it would be more of a disappointment than a failure.”