G Herbo has released the official video for “Win Again,” a standout track from his project Lil Herb.
Directed by Mark Cukier and MilkyMadeIt, the visual captures the tension between success and responsibility. Herbo is shown navigating a fast-paced lifestyle, from private flights to studio sessions and late nights, while balancing the pressure that comes with it.
The video leans into the song’s themes of resilience, loyalty and the cost of constant motion. It avoids glamorizing success without showing its weight, offering a more grounded look at the rapper’s journey.
A key presence throughout the visual is his son, Yosohn Santana Wright, whose appearances add emotional depth and highlight Herbo’s sense of purpose beyond music.
“Win Again” continues to build on the narrative of Lil Herb, a 15-track project that reflects on growth, loss and the realities of staying true while moving forward.