Sep 20, 2025
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.
• 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.
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/