The Chopping Block: Gabriel Shapiro on Why Sam Bankman-Fried May Be a ‘Sociopath’ – Ep. 555

Welcome to The Chopping Block – where crypto insiders Haseeb Qureshi, Tom Schmidt, Tarun Chitra, and chop it up about the latest news. This week, the crew is joined by Gabriel Shapiro, general counsel at Delphi Labs, to talk about the key points in the criminal trial of Sam Bankman-Fried and his lackluster defense strategy so far. They also delve into Michael Lewis’ book and his depictions of SBF’s “lore and backstory,” and discuss how SBF’s “quirks of character” may have actually enticed investors.

Listen to the episode on Apple Podcasts, Spotify, Overcast, Podcast Addict, Pocket Casts, Stitcher, Castbox, Google Podcasts, TuneIn, Amazon Music, or on your favorite podcast platform.

Show highlights: 

How Haseeb’s previous comments on Sam Bankman-Fried’s intentions “didn’t age well” after developments in the trial

Why Gabriel believes that SBF is a “sociopath” and should have taken a plea deal if offered

Shortcomings in the defense’s strategy and why Gabriel believes they’re “grasping at straws”

How the fake numbers of FTX insurance fund highlight the weaknesses of a centralized exchange

Why Matt Huang, cofounder of VC firm Paradigm, agreed to testify in such a high-profile trial, and why Haseeb as a VC himself wouldn’t have done it

Whether SBF understood the technical components of crypto and why he sounded like ChatGPT in his responses, according to Tarun

Whether VCs are to blame for investing in FTX or what lessons VCs need to take away from the SBF debacle. 

The differences and similarities between SBF and Binance CEO Changpeng Zhao


Haseeb Qureshi, managing partner at Dragonfly 

Tom Schmidt, general partner at Dragonfly 

Tarun Chitra, managing partner at Robot Ventures


Gabriel Shapiro, General counsel of Delphi Labs

Previous appearances on Unchained:

Are DAOs Strong Enough to Survive the Regulators?

What Does Mango Markets Exploiter Avi Eisenberg’s Arrest in Puerto Rico Mean for DeFi?

Disclosures Links

Previous coverage of Unchained on the trial of Sam Bankman-Fried:

Sam Bankman-Fried Trial: Here’s Everything That Happened So Far

SBF Trial, Day 1: Possible Witnesses Include FTX Insiders, Big Names in Crypto, and SBF’s Family

SBF Trial, Day 2: DOJ Says Sam Bankman-Fried ‘Lied’ While Defense Claims His Actions Were ‘Reasonable’

SBF Trial, Day 3: Why a True Believer in FTX Flipped Once He Learned One Fact

SBF Trial, Day 4: SBF’s Lawyers Annoy Judge Kaplan, While Wang Reveals Alameda’s Special Privileges

SBF Trial, Day 5: SBF’s Defense Finally Found Its Legs, But Can It Counter Caroline Ellison?

SBF’s Lawyers Could Be Annoying the Judge. How Might That Impact the Trial?

Did Sam Bankman-Fried Have Intent to Defraud FTX Investors?

Here’s How Sam Bankman-Fried’s High-Stakes Trial Could Play Out

SBF Trial: How Sam Bankman-Fried’s Lawyers Might Try and Win His Case

The High-Stakes Trial of Sam Bankman-Fried Begins: What to Expect

FTX Used a Fake Number to Beef Up Its Insurance Fund: Gary Wang

Previous coverage of the trial elsewhere: 

NYT: What FTX’s Sam Bankman-Fried and J.P. Morgan Have in Common

Forbes: Sam Bankman-Fried Knew Plenty About His Alameda Research Hedge Fund–And Sent Details To Forbes Just Months Ago

Tarun’s tweet on insurance funds being onchain

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