United States v. Ulbricht
858 F.3d 71
| 2d Cir. | 2017Background
- Ross Ulbricht created and operated Silk Road (anonymity via Tor; Bitcoin-based marketplace) and was arrested in Oct. 2013; jury convicted him on seven counts including narcotics distribution, conspiracy, CCE, computer crimes, ID fraud, and money laundering; life sentence imposed.
- Government used pen/trap orders to collect IP/TCP routing metadata from Ulbricht’s home router and devices; agents also obtained warrants to search Ulbricht’s laptop and his Google and Facebook accounts.
- Key evidence: DPR’s private PGP key and extensive Silk Road files, chats, journals, server lists, and Bitcoin wallets found on Ulbricht’s laptop; travel records corroborating online posts; blockchain analysis linking Silk Road proceeds to wallets seized.
- Two undercover agents (Force and Bridges) engaged in corruption (stealing Bitcoins, extortion); government disclosed Force investigation pretrial (partially sealed) and Bridges’s misconduct post-trial; Ulbricht sought to use this information at trial and in a Rule 33 motion.
- District court excluded certain evidence (e.g., Force-related chats, late expert witnesses, some cross-examination topics, a hearsay government letter about administrator Andrew Jones) and denied extensive discovery and a trial continuance related to the Force grand jury; sentenced Ulbricht to life after finding (by a preponderance) he commissioned five murders and considering six drug-related deaths as relevant conduct.
Issues
| Issue | Ulbricht's Argument | Government's Argument | Held |
|---|---|---|---|
| Pen/trap metadata collection (IP/TCP) — Fourth Amendment | Pen/trap orders (no warrant) invaded reasonable privacy in IP/TCP routing data; warrant required | IP/TCP routing metadata are third-party subscriber/routing info analogous to numbers captured by telephone pen registers; no content seized; Pen/Trap Act authorized orders | Collection of IP/TCP routing metadata without warrant did not violate Fourth Amendment; no reasonable expectation of privacy in such third-party routing data (affirmed) |
| Particularity of search warrants (laptop, Google, Facebook) | Warrants too broad for digital media; insufficiently particular (search terms/protocols not specified) causing general warrant risk | Warrants (with incorporated affidavits) specified crimes, places, and items related to Silk Road/DPR identification; breadth justified by nature of digital evidence; agents did best given circumstances | Warrants were sufficiently particular for electronic search; protocols and broad categories permissible given probable cause and the nature of offenses (affirmed) |
| Evidence re: corrupt agents (Force/Bridges) — Brady/Disclosure/Discovery | Late/sealed disclosures of agents’ misconduct deprived Ulbricht of Brady material and relevant impeachment; denied discovery and continuance prejudiced defense | Government disclosed Force investigation under protective order, purged Force-derived trial evidence, and the agents’ misconduct did not implicate the provenance or reliability of the admissible evidence used at trial | Disclosure timeliness/delays did not violate Brady because agent misconduct was not shown to be exculpatory or to taint trial evidence; district court did not abuse discretion in limiting discovery/denying continuance (affirmed) |
| Exclusion of defense expert witnesses (Rule 16) | Preclusion of Bellovin and Antonopoulos deprived Ulbricht of needed technical rebuttal; disclosures were effectively timely | Defendant’s expert notices were late and substantively inadequate under Rule 16(b); prejudice to government and impracticality of continuance justified exclusion | Preclusion was proper: disclosures were untimely and vague; district court reasonably exercised discretion (affirmed) |
| Limitation on cross-examination of government witnesses | Court unduly curtailed cross-examination re: alternative-perpetrator theories and technical points | Exclusions were within scope limits, prevented speculation, and avoided jury confusion; defense had substantial cross-examination elsewhere | Limits were within trial court discretion; any error was harmless given other admitted cross-examination and overwhelming evidence (affirmed) |
| Admission of hearsay (DeathFromAbove chats; Andrew Jones statement) | Chats and government letter were admissible (non-hearsay or under exceptions) to show agent involvement/alternate DPRs | Statements were hearsay (and double hearsay); not sufficiently trustworthy or admissible under exceptions; risk of confusion and lack of probative value | Exclusions were proper under hearsay rules; alternative-perpetrator inference was speculative; any error harmless (affirmed) |
| Rule 33 new-trial motion based on Force/Bridges disclosure | Newly disclosed agent corruption warrants new trial under Brady | Agent misconduct did not render trial unfair or undermine verdict; no material suppressed | District court did not abuse discretion denying Rule 33; no Brady violation shown (affirmed) |
| Procedural and substantive reasonableness of life sentence | Sentence is excessive, procedurally flawed by reliance on six drug-related deaths and general deterrence; life sentences rare and disproportionate | District court properly calculated Guidelines, considered §3553(a) factors, found commission/payment for five murders; deaths were relevant conduct; life sentence within discretion | Sentence procedurally and substantively reasonable: court’s findings (murders, relevant deaths) supported by preponderance; life sentence not an abuse of discretion (affirmed) |
Key Cases Cited
- Smith v. Maryland, 442 U.S. 735 (1979) (third-party pen-register doctrine; no expectation of privacy in numbers dialed)
- Kyllo v. United States, 533 U.S. 27 (2001) (warrant required for certain sense-enhancing surveillance of the home)
- Brady v. Maryland, 373 U.S. 83 (1963) (prosecution must disclose exculpatory/impeachment evidence)
- United States v. Ganias, 824 F.3d 199 (2d Cir. en banc 2016) (digital-search particularity and retention issues)
- United States v. Galpin, 720 F.3d 436 (2d Cir. 2013) (particularity for computer searches)
- United States v. Forrester, 512 F.3d 500 (9th Cir. 2008) (no expectation of privacy in IP address/routing data)
- United States v. Christie, 624 F.3d 558 (3d Cir. 2010) (subscriber/IP information not protected)
- United States v. Jones, 565 U.S. 400 (2012) (modern technology and Fourth Amendment; concurrences questioning third-party doctrine scope)
- Apprendi v. New Jersey, 530 U.S. 466 (2000) (jury-trial implications for facts increasing statutory penalties)
- United States v. Carpenter, 819 F.3d 880 (6th Cir. 2016) (discussing Fourth Amendment protection for certain historical location metadata)