Bad at Sports Episode 925: Nicholas DiLeonardi (Gitler&_____)

Feb 10, 2026

Nicholas DiLeonardi (Gitler&_____)
Recorded in Miami during art fair week

Nicholas DiLeonardi joins Bad at Sports from the middle of Miami art fair week, not from a booth but from the pavement between them. Assistant Director and consultant at Gitler&_____, DiLeonardi spends the week moving between fairs, collectors, hammocks, robot dogs, and banana sightings, offering a ground-level view of what art fairs actually feel like when you are advising clients rather than selling from behind a wall.

The conversation moves fluidly from ranking fairs to questioning the psychic cost of sitting in a booth, from the pleasures of approachable painting to skepticism about over-packaged meaning. DiLeonardi talks candidly about advising as a practice, collecting as a responsibility, and why sometimes the best work is the work that does not want to explain itself. Along the way, the group unpacks the strange theater of Art Basel, the social logic of NADA, the pleasures and limits of Untitled, and what it means to keep showing up to a system that is both exhausting and irresistible.

The episode also dives into Gitler&____’s public-facing projects, including the long-running Audubon Mural Project, and the blurred line between consultancy, gallery work, and artist support. It is a conversation about taste, access, labor, exhaustion, and the odd hope that keeps people flying back to Miami year after year.

Recorded live, with roosters, bridges, hammocks, and just enough art world self-awareness to stay funny.

Highlights & Moments

• Ranking Miami fairs while openly admitting bias
• Why NADA still feels like a New York fair dropped into Miami
• Hammocks as both seating and market distortion
• Untitled as the gateway fair for first-time collectors
• The Beeple robot dog spectacle and the freedom of not knowing how to feel about it
• Counting banana references across satellite fairs
• “No motive” painting and the desire for unmediated experience
• Art advising as a creative practice rather than pure transaction
• The psychic toll of booth sitting and forced enthusiasm
• Why pre-selling booths feels like theater everyone agrees to perform

 

Names Dropped:

·       Art Basel Miami Beach — https://www.artbasel.com/miami-beach

·       NADA Miami (New Art Dealers Alliance) — https://thenada.org/nada-miami

·       Untitled Art Fair — https://untitledartfairs.com/

·       Scope Art Show — https://scope-artshow.com/ 

·       Audubon Mural Project — https://www.audubon.org/muralproject

·       National Audubon Society — https://www.audubon.org/

·       Beeple (Mike Winkelmann) coverage — https://www.artnews.com/art-news/news/beeple-pooping-robot-dogs-at-art-basel-miami-beach-1234765375/

·       Robert Moskowitz- https://en.wikipedia.org/wiki/Robert_Moskowitz

·       Andrew Spence- https://andrewspenceart.com

·       Western Exhibitions- https://westernexhibitions.com

·       Submissions- https://www.submissions.art

·       Canada Gallery- https://canadagallery.com

·       Mac’s Club- https://www.macsclubdeuce.com

·       Gitler&____- https://www.gitlerand.com/