Sheppard took a significant step forward during his second NBA season, earning a regular rotation role for Houston and showcasing the efficient, high-IQ game that made him a lottery pick in the 2024 NBA Draft. He averaged 13.5 points, 3.4 assists, 2.9 rebounds and 1.5 steals per game while shooting 39.4 percent from beyond the arc and finishing sixth in the 2025-26 Sixth Man of the Year voting. Entering 2026-27, Sheppard is expected to have a steady role off the bench, though his minutes and workload could decrease with the return of Fred VanVleet, who missed the entire 2025-26 campaign due to a knee injury. His fantasy appeal stems from his ability to contribute efficiently across multiple categories without requiring high usage, particularly through three-pointers, assists and steals. While he may never develop into a high-volume scorer, his excellent shooting percentages and low-turnover profile make him an appealing late-round target who should be particularly useful in category-based leagues. That said, his fantasy potential has a ceiling since he'll likely come off the bench on a contending team.