The impact factor or journal impact factor of an polymer chemistry academic journal is a scientometric index that reflects on the yearly average number of citations that articles publish and gain impact by the reader and authors. Polymer-based drug delivery systems may significantly improve cancer therapy. We developed amphiphilic poly(ε-caprolactone)-graft-(poly-N-(2-hydroxypropyl) methacrylamide) copolymers (PCL-graft-pHPMA) with tunable amphiphilicity intended for efficient dual delivery via simultaneous encapsulation of hydrophobic drug, Bcl-2 inhibitor ABT-199, and pH-sensitive conjugation of other chemotherapeutics, doxorubicin, to desired sites, e.g. tumors. Using controlled RAFT polymerization and click chemistry well-defined PCL-graft-pHPMA of diverse Mw and physical properties were prepared. By simple dissolution they self-assembled into highly stable micelles with Dh ≈ 25 nm and low critical micelle concentration (around 5 μg mL−1). The total drug payload reached 17 wt% while maintaining system solubility. The micelles exhibited long-term stability in buffers.