There is a tremendous unmet medical need for osteoarthritis (OA) treatment around the world, and pharmacological management is the most common option but presents a limited and short efficacy. Insufficient drug delivery to articular cartilage is the key cause. It is widely accepted that the complex structure of articular cartilage and the rapid clearance of joint liquids largely hinder drug penetration and retention in the cartilage. To address these obstacles, we designed and prepared a positively charged micellar system that can effectively deliver a model drug to the deep zone of the cartilage and prolong the drug retention time. In this work, a triblock copolymer composed of cationic poly(N,N-dimethylaminoethyl methacrylate) (PDMAEMA) and poly(ε-caprolactone) (PCL), denoted as PDMAEMA-PCL-PDMAEMA, was synthesized. A triblock copolymer composed of brush poly[poly(ethylene glycol) methacrylate] (pPEGMA) and PCL, denoted as pPEGMA-PCL-pPEGMA, was prepared for comparison. The two types of triblock copolymers were self-assembled in an aqueous environment to form cationic and neutral micelles, respectively. A hydrophobic fluorescent dye as a model drug was loaded into micelle cores, and the dye-loaded micelles were evaluated for intra-cartilage penetration and retention using porcine knee cartilage explants. The PDMAEMA-PCL-PDMAEMA cationic micelles were found to significantly enhance the intra-cartilage penetration and retention capability due to the electrostatic interaction between the micelles and the negatively charged cartilage extracellular matrix. The confocal microscopy study showed that the cationic micelles could penetrate the full-thickness porcine cartilage explants (around 1.5 mm) within 24 hours. Up to 87% of the cationic micelles were taken up by porcine cartilage explants, and 71% of the absorbed micelles were retained in the tissue for at least 4 days. Although the pPEGMA-PCL-pPEGMA neutral micelles were able to penetrate the full-thickness cartilage, this type of micelle showed lower uptake (44%) and retention (44%) rates. This observation implied that the surface charge of micelles could play an important role in efficient intra-cartilage drug delivery. This study verified the feasibility and effectiveness of the PDMAEMA-PCL-PDMAEM cationic micelles in intra-cartilage drug delivery, showing that cationic micelles could be promising carriers for OA treatment.