Bad Boys of Bankruptcy: S3E4: Don’t Cash That Until Friday: The Najeeb Khan Check-Kiting Scheme episode artwork

EPISODE · Mar 13, 2026 · 36 MIN

Bad Boys of Bankruptcy: S3E4: Don’t Cash That Until Friday: The Najeeb Khan Check-Kiting Scheme

from To the Extent That... · host ABA Business Law Section

In this episode, Judge Gunn is joined by attorneys Nick Miller and Mark Iammartino to discuss the unwinding of one of the largest check-kiting schemes in modern history. Najeeb Khan operated a successful payroll processing company in Indiana in the early 2000s. At some point around 2011, Khan began embezzling funds from his payroll processing company and using an elaborate check-kiting scheme to cover up the missing funds. Between 2011 and 2019, Khan embezzled an estimated $73 million from the scheme, which he used to purchase one of the largest classic car collections in the country (consisting of more than 250 cars including at least one that could also be used as a boat), several airplanes, and multiple luxury residences in Michigan, Florida, and Arizona. The scheme came crashing down in 2019, when Khan abruptly halted the musical chairs of worthless checks he was circulating, leaving Key Bank holding the bag for over $140 million in losses based on funds Khan had wired out of a Key Bank account based on provisional account credits issued against ultimately worthless checks. Mark Iammartino, the Chapter 7 trustee in one of the fifteen (15) bankruptcy cases that resulted from the scheme collapsing, discusses the venue fight that arose when the payroll processing company (and several related entities) filed bankruptcy in Michigan while Khan and a handful of affiliated management companies filed bankruptcy cases in Indiana shortly thereafter, the unusual steps taken to liquidation Khan’s massive classic car collection during the COVID-19 pandemic (which resulted in auction proceeds of over $40 million), and the other steps taken by the trustees and committees to marshal assets and attempt to compensate victims of Khan’s scheme. Khan later pled guilty to bank fraud and attempted tax evasion in a federal criminal case, and was sentenced to just over eight years in prison, and was ordered to pay $148 million in restitution and nearly $10 million in back taxes.

In this episode, Judge Gunn is joined by attorneys Nick Miller and Mark Iammartino to discuss the unwinding of one of the largest check-kiting schemes in modern history. Najeeb Khan operated a successful payroll processing company in Indiana in the early 2000s. At some point around 2011, Khan began embezzling funds from his payroll processing company and using an elaborate check-kiting scheme to cover up the missing funds. Between 2011 and 2019, Khan embezzled an estimated $73 million from the scheme, which he used to purchase one of the largest classic car collections in the country (consisting of more than 250 cars including at least one that could also be used as a boat), several airplanes, and multiple luxury residences in Michigan, Florida, and Arizona. The scheme came crashing down in 2019, when Khan abruptly halted the musical chairs of worthless checks he was circulating, leaving Key Bank holding the bag for over $140 million in losses based on funds Khan had wired out of a Key Bank account based on provisional account credits issued against ultimately worthless checks. Mark Iammartino, the Chapter 7 trustee in one of the fifteen (15) bankruptcy cases that resulted from the scheme collapsing, discusses the venue fight that arose when the payroll processing company (and several related entities) filed bankruptcy in Michigan while Khan and a handful of affiliated management companies filed bankruptcy cases in Indiana shortly thereafter, the unusual steps taken to liquidation Khan’s massive classic car collection during the COVID-19 pandemic (which resulted in auction proceeds of over $40 million), and the other steps taken by the trustees and committees to marshal assets and attempt to compensate victims of Khan’s scheme. Khan later pled guilty to bank fraud and attempted tax evasion in a federal criminal case, and was sentenced to just over eight years in prison, and was ordered to pay $148 million in restitution and nearly $10 million in back taxes.

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Bad Boys of Bankruptcy: S3E4: Don’t Cash That Until Friday: The Najeeb Khan Check-Kiting Scheme

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In this episode, Judge Gunn is joined by attorneys Nick Miller and Mark Iammartino to discuss the unwinding of one of the largest check-kiting schemes in modern history. Najeeb Khan operated a successful payroll processing company in Indiana in the...

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