Gilbert Arenas is navigating contract uncertainty with Underdog Fantasy regarding the future of his podcast. A guest-hosting appearance raised questions about the direction of his basketball show. 

A recent absence from his programming led to media speculation after Skip Bayless filled in on the May 20, 2026, episode. Bayless guest-hosted the show while the founder was away during an ongoing contract uncertainty with Underdog Fantasy. 

Addressing the situation on May 27, Gilbert Arenas shared a video from his new personal studio setup, which was posted by the X account @Thechat101. In the video, he emphasized his ownership and independence by pointing to his original branding. “This channel says Gil's Arena. It says it,” stated Arenas.

The public perception of his standing within the company became a central focus of the controversy. “I’m not sure they like ME anymore,” Arenas said via Clutch Points.

“When people start writing, the team is better without them, that player reads it."

The missed episode occurred on May 20, which Arenas later described as a scheduled vacation and “Finals duty.”

Arenas also attempted to cool down the growing speculation. He offered clarifications in his video, stating, “Nothing happened. No beef,” and added, “Me and Skip, we play golf every Wednesday.” He insisted that Bayless was never brought in to replace him, noting, “Skip came there for me.” 

Bayless was already involved with the network's separate football project before this basketball controversy started.

Arenas' contract expired before the rest of the cast, giving him flexibility. He can walk away with the Gil's Arena identity and rebuild everything independently.

While Underdog controls the current production and staffing, Arenas still owns the brand and holds the audience's loyalty. This leads to the backstory behind their initial partnership.

How Gilbert Arenas’ Underdog Partnership Turned Into Public Negotiation Drama

The show started in a simple setup back in 2023, with former NBA players like Kenyon Martin, Brandon Jennings, and Rashad McCants. To grow the brand, an agreement was signed with Underdog in October 2025.

This deal involved selling around 50% ownership in exchange for a better overall structure of the show. 

The channel rebranded into “The Arena presented by Underdog.” However, Arenas retained the intellectual property, branding, and format rights.

Bayless joined the company's expansion plans in August 2025 for The Arena: Gridiron football project. This is why Arenas insists Bayless was always meant as a network addition rather than a direct replacement. 

Reaffirming his position, Arenas reiterated that he built the platform from scratch and possesses the ability to do it again independently. The situation looks far more like public contract leverage than a business breakup. 

What are your thoughts on creator ownership in sports media? Read more at Air Jordan Chronicles! 

Written by

Utsav Sinha

Edited by

Koushik Biswas