AI technologies continue to advance from digital assistants to assisted decision-making. However, designing AI remains a challenge given its unknown outcomes and uses. One way to expand AI design is by centering stakeholders in the design process. We conduct co-design sessions with gig workers to explore the design of gig worker-centered tools as informed by their driving patterns, decisions, and personal contexts. Using workers’ own data as well as city-level data, we create probes—interactive data visuals—that participants explore to surface the well-being and positionalities that shape their work strategies. We describe participant insights and corresponding AI design considerations surfaced from data probes about: 1) workers’ well-being trade-offs and positionality constraints, 2) factors that impact well-being beyond those in the data probes, and 3) instances of unfair algorithmic management. We discuss the implications for designing data probes and using them to elevate worker-centered AI design as well as for worker advocacy.