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Unusual self‐assembly behavior is observed for a range of hydrophilic homopolymers. This self‐assembly behavior is contrary to the expected behavior of such hydrophilic polymers and instead mimics more commonly reported amphiphilic block copolymers. It is proposed that the unique combination of hydrophobic end groups at both the α and ω chain end accounts for this unusual self‐assembly behavior. Complex internal polymer micelles are spontaneously formed when hydrophilic homopolymer polyelectrolytes and neutral polymers (with a weight fraction of the hydrophobic end groups <10 wt%) are directly dissolved in water. The homopolymers, poly[2‐(diethylamino)ethyl methacrylate], poly(N‐isopropylacrylamide), and poly(ethoxyethylacrylate) are synthesized by reversible addition–fragmentation chain‐transfer (RAFT) polymerization using S′‐1‐dodecyl‐(S′)‐(α,α′‐dimethyl‐α″‐acetic acid …