This study assesses whether self-supervised learning (SSL) improves knee osteoarthritis (OA) modeling for diagnosis and prognosis relative to ImageNet-pretrained initialization. We compared (i) image-only SSL pretrained on knee radiographs from the OAI, MOST, and NYU cohorts, and (ii) multimodal image-text SSL pretrained on uncurated hospital knee radiographs paired with radiologist impressions. For diagnostic Kellgren-Lawrence (KL) grade prediction, SSL offered mixed results. While image-only SSL improved accuracy during linear probing (frozen encoder), it did not outperform ImageNet pretraining during full fine-tuning. Similarly, multimodal SSL failed to improve grading performance. We attribute this to severe bias in the uncurated hospital pretraining corpus (93% estimated KL grade 3), which limited alignment with the balanced diagnostic task. In contrast, this same multimodal initialization significantly improved prognostic modeling. It outperformed ImageNet baselines in predicting 4-year structural incidence and progression, including on external validation (MOST AUROC: 0.701 vs. 0.599 at 10% labeled data). Overall, while uncurated hospital image-text data may be ineffective for learning diagnosis due to severity bias, it provides a strong signal for prognostic modeling when the downstream task aligns with pretraining data distribution