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Adaptation of cyclic brush polymer for drug delivery applications remains largely unexplored. Herein, cyclic brush copolymer of poly(2‐hydroxyethyl methacrylate‐g‐poly(N‐isopropylacrylamide‐st‐N‐hydroxyethylacrylamide)) (cb‐P(HEMA‐g‐P(NIPAAm‐st‐HEAAm))), comprising a cyclic core of PHEMA and thermosensitive brushes of statistical copolymer of P(NIPAAm‐st‐HEAAm), is designed and synthesized successfully via a graft‐from approach using atom transfer free radical polymerization from a cyclic multimacroinitiator. The composition of the brush is optimized to endow the resulting cyclic brush copolymer with a lower critical solution temperature (LCST) slightly above the physiological temperature, but lower than the localized temperature of tumor tissue, which is suitable for the hyperthermia‐triggered anticancer drug delivery. Critical aggregation concentration determination reveals better stability for the …