In Part Two of our late-night conversation, Bad at Sports digs deeper into the remarkable trajectory of Kenny Schachter. From law school dropout to autodidact philosopher, from Sotheby’s bidder to artist and teacher, Schachter traces the unlikely path that brought him into the heart of the art world — a place he insists remains strangely conservative despite all its pretenses of progress. The discussion moves between personal history and systemic critique. Schachter recounts the role of art in surviving trauma, loss, and addiction, and why surrounding himself with works by others has been both solace and education. He reflects on the stubborn conservatism of the market, celebrity crossovers from Johnny Depp to Julian Schnabel, and the tension between wanting freedom and the systems that resist it. For Schachter, art is both a lifeline and a way to comment on the world’s chaos — a practice rooted in generosity, curiosity, and contradiction. This episode captures him at his most reflective and most biting, moving from humor to vulnerability and back again.

Highlights

• Schachter’s first encounters with Twombly, Rauschenberg, and Frankenthaler at the National Gallery.

• The shock of Andy Warhol’s estate sale in 1988.

• Dealer-to-dealer hustling as an unlikely entry into art.

• Why “there are no rules” is his best definition of being an artist.

• The paradox of an art world that markets rebellion but runs on tradition.

Names Dropped

Andy Warhol I.M. Pei, https://www.pcf-p.com/about/i-m-pei/ Chase Manhattan Bank, https://www.jpmorganchase.com/about/art-collection Christie’s, https://www.christies.com/en Sotheby’s, https://www.sothebys.com/en/ Phillips Auction House, https://www.phillips.com/ Patrick Drahi, https://www.artnews.com/art-collectors/top-200-profiles/patrick-drahi/ Leonard Lauder, https://www.artnews.com/art-news/news/leonard-lauder-sothebys-klimt-matisse-1234751922/ The Pritzker family, https://www.artnews.com/art-news/news/pritzker-art-collection-sothebys-breuer-1234751864/ Elaine Wynn, https://www.christies.com/en/events/the-collection-of-elaine-wynn Wyatt Kline, https://unframed.lacma.org/2014/01/28/contemporary-friends-acquire-ten-new-works-by-artists-from-around-the-world Alex Burns, Felix Reuter (Ryder), https://felixreuter.bandcamp.com/ Guerrilla Girls, https://www.guerrillagirls.com/ Old Friends Gallery, https://www.oldfriendsgallery.com/ David Letterman, https://en.wikipedia.org/wiki/David_Letterman The Suburban, http://www.thesuburban.org/