Big Time Podcast Summary: "The Stupendous Shirley S." Episode 7

Release Date: May 5, 2025
Host: Steve Buscemi
Produced by: Campside Media and Piece of Work Entertainment

Introduction

In episode 7 of Apple’s original podcast Big Time, hosted by Steve Buscemi, listeners are introduced to the fascinating and tumultuous life of Shirley S., a woman whose penchant for adventure led her into the shadowy corners of the art underworld. Titled "The Stupendous Shirley S.," this episode delves deep into Shirley’s elaborate schemes, her relationship with Albert Sack, and the consequences of her audacious criminal endeavors.

Background: Albert Sack and the Meeting with Shirley

The story begins with an introduction to Albert M. Sack, a 20th-century pioneer in American antiquing. Born in 1915, Albert transformed antiquing into a popular hobby through his guidebook, Fine Points of Furniture, and gained fame as a regular on Antiques Roadshow. His expertise and reputation attracted high-profile clients, including Barbara Streisand and Harrison Ford, and earned a section in the Metropolitan Museum of Art for his family's furniture collection.

Albert was an eligible bachelor until he met Shirley, an elegant and charismatic art dealer from Boston. Their first encounter was unconventional; on their first date at the airport, Shirley, adorned in a frilly dress, half-jokingly asked Albert, "Will you marry me?" (00:00, Steve Buscemi). Intrigued and captivated, Albert quickly fell for her, unaware of the complex future that awaited them.

Shirley’s Descent into the Art Underworld

Shirley, née Dorothy Zacks Silberg Silton, was not born into wealth. Her parents were Orthodox Jewish immigrants from Russia who lived modestly. However, Shirley developed an affinity for the finer things in life, leading her to a successful career as an art consultant in Boston. Despite several failed marriages, her drive and unique approach to business made her stand out.

Deborah Friedman, Shirley’s eldest daughter, provides insight into her mother’s character, recalling how Shirley managed artists and even orchestrated insurance scams to support her endeavors (04:26). Shirley’s criminal inclinations became more pronounced when she connected with Eddie DiPietro, a dangerous and violent crook (07:14, Anthony Amore). Acting as the brains behind art theft operations, Shirley became adept at fencing stolen artwork, leveraging her reputation in the art world to facilitate these illicit transactions.

The Harvard Art Heist

One of Shirley’s most audacious crimes was the theft of paintings from Harvard University’s president, Derek Bok’s private residence in Cambridge on July 7, 1976. Shirley’s crew forcefully accessed the mansion, stealing valuable impressionist and landscape paintings valued at over $350,000. This operation marked Shirley’s deep dive into high-stakes art theft.

Following the heist, Shirley attempted to fence the stolen art, which is when she met Albert Sack. Their relationship blossomed, leading to marriage despite Albert’s family’s disapproval. Deborah Friedman describes Albert as a "mensch" and "ubermensch," highlighting his unwavering support for Shirley, even as her criminal activities became more entangled (09:42).

Marriage and Continued Criminal Activities

Albert’s devotion to Shirley was evident as he stood by her through her arrest for the Harvard theft, earning Shirley the FBI nickname "the Finger" (10:31). Despite the tarnished optics of being associated with a convicted art thief, Albert’s commitment never wavered. He maintained their bond by visiting Shirley in prison regularly, bringing her comforts like Dunkin’ Donuts and beauty products (10:58).

Upon Shirley's release from prison after serving her sentence, Albert and she moved to a luxurious Manhattan apartment on East 56th Street, transforming it into a display of both Albert’s antiques and Shirley’s dubious art acquisitions. Their home became a symbol of their complex relationship—where legitimacy and illegality coexisted harmoniously.

Shirley’s Ruby Scheme and Downfall

In the late 1980s, Shirley shifted her focus to gems, aspiring to elevate her status and regain the spotlight. She ventured into Myanmar to broker deals with General Kunsa Khun Sa, a notorious warlord and opium trafficker. Shirley’s plan was to facilitate the sale of rubies to replace the drug trade, blending humanitarian motives with financial gain (15:09, Alyssa).

However, Shirley’s venture unraveled disastrously. The deal fell through as the rubies were not as valuable as anticipated, plunging her into significant debt. Forced to close her jewelry business, Shirley returned to art dealing, further entangling herself in deceit by selling fake masterpieces alongside Albert’s genuine antiques (19:59). Despite Albert’s high-end antique sales, Shirley’s mounting credit card debt led her into more fraudulent activities, culminating in a failed attempt to sell paintings to an undercover FBI agent in 2001.

The Final Bust and Legal Consequences

In May 2001, Shirley, along with conspirator Arnold Katzen, attempted to sell two paintings worth $4.1 million at the Ritz-Carlton Hotel in Boston. Unbeknownst to them, the buyer was an undercover FBI agent monitoring their activities. The sting operation led to their arrest, with Shirley facing severe legal repercussions. Deborah Friedman recounts the family's turmoil, highlighting Shirley’s reckless endangerment of her loved ones (22:16).

Ultimately, Shirley pleaded guilty to conspiracy charges, avoiding a trial by accepting three years of probation, a stark contrast to the potential 20-year sentence she faced (23:11). Katzen received a similar probationary sentence. The legal battle left Albert and Shirley financially devastated, forcing them to relocate to North Carolina to live with Deborah’s family.

Legacy and Conclusion

Albert’s unwavering support for Shirley, despite her continual descent into criminality, became a point of both admiration and frustration for the family. Their New York apartment, once a beacon of luxury and artistry, became a symbol of their intertwined lives of legitimacy and fraud. Albert passed away in 2011 at the age of 91, followed by Shirley in 2019 at age 96.

Posthumously, Albert’s antiques were donated to museums, preserving his legacy in the art world. Meanwhile, Shirley’s collection of fake paintings remains with Deborah, serving as a testament to her audacious spirit and complex legacy.

Notable Quotes:

• Steve Buscemi (00:00): “You get the rush of the bank robbery or the romance of a torrid affair without having to risk it all.”

• Deborah Friedman (03:00): “Everyone knows about my mother now.”

• Deborah Friedman (09:42): “I thought, this is a mensch. Above all, mensches. This is an ubermensch.”

• Alyssa (12:46): “Albert was the only grandfather I knew.”

• Deborah Friedman (14:07): “There were people that shunned him. There were people that would invite him to things and not invite her.”

• Steve Buscemi (16:57): “We rely on you, ma'am.”

• Abby Ellen (25:07): “Albert's love for Shirley was so fucking blind.”

Conclusion

Big Time’s episode on Shirley S. paints a vivid portrait of a woman driven by a desire for adventure and recognition, whose ambitions led her down a path of elaborate scams and artistry-based crimes. Through meticulous storytelling and firsthand accounts, the podcast captures the essence of Shirley’s complex character and the enduring impact of her actions on her family and the art world.

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