April 9th, 2026
More than a century after the tragic sinking of the RMS Titanic, one of its most poignant personal stories is about to resurface — not in the icy waters of the North Atlantic, but under the bright lights of a Chicago auction room. On April 26, Freeman's will present two extraordinary artifacts recovered from the body of John Jacob Astor IV: an 18-karat gold pocket watch and a gold pencil case, together estimated at $300,000 to $500,000.
The pairing offers a rare glimpse into the personal effects of one of the wealthiest men aboard the ill-fated liner. Astor, a real estate magnate and heir to one of America’s most prominent fortunes, carried the elegant timepiece — crafted by Patek Philippe and retailed by Tiffany & Co. — during what would become his final journey.
Made of 18-karat yellow gold and engraved with Astor’s monogram, it reflects the understated sophistication of the Gilded Age elite. Accompanying it is a 14-karat gold pencil case, a small but telling accessory that speaks to an era when even the most utilitarian objects were elevated through fine craftsmanship. Together, they were among the items recovered from Astor’s body days after the Titanic slipped beneath the waves in April 1912.
The backstory adds a deeply human dimension to these glittering relics. Astor, 47 at the time, was traveling with his young second wife, Madeleine Astor, who was just 18 and pregnant. Their marriage had stirred intense public scrutiny due to their age difference, prompting an extended honeymoon abroad.
When the Titanic struck an iceberg, Astor ensured Madeleine’s safety, helping her into a lifeboat. He famously asked if he could accompany her due to her “delicate condition,” but was denied under the “women and children first” protocol. Witnesses recall him calmly stepping back, kissing his wife goodbye and promising, “I’ll see you in New York.” He never made it.
According to Freeman's, the 18-karat gold pocket watch was purchased by Astor from Tiffany & Co. in New York in 1904. After the Titanic disaster, the watch and pencil were returned to Astor's son, Vincent Astor, who wore the watch throughout his life until his death in 1959. The watch subsequently passed through successive generations of the family:
What makes this upcoming sale particularly intriguing is the high-profile existence of another “Astor watch.” In April 2024, British auction house Henry Aldridge & Son sold a 14-karat gold Waltham pocket watch — also attributed to Astor — for a staggering $1.485 million, setting a record at the time for Titanic memorabilia.
Official recovery records from 1912, however, indicate that only one watch was found on Astor’s body.
That discrepancy has sparked ongoing debate in the auction world. Freeman’s maintains that its Patek Philippe example holds the strongest claim to authenticity, citing uninterrupted ownership within the Astor family for more than 120 years, along with archival documentation. The competing watch, while undeniably historic, followed a more circuitous path through private hands.
In the lead-up to the 2024 auction, Henry Aldridge & Son recounted how the real estate magnate’s possessions were turned over to Astor’s son, Vincent, who had the gold watch completely restored. Vincent reportedly wore the watch regularly, but in 1935, presented it as a christening gift to the infant son of William Dobbyn IV, John Jacob Astor’s executive secretary and confidant. The watch would remain in the Dobbyn family until it was auctioned in the late 1990s.
Credits: Auction items, Astor photo and newspaper front page courtesy of Freeman’s. Photo of John Jacob Astor IV and his wife, Madeleine, circa early 1910s. Public domain, via Wikimedia Commons.
The pairing offers a rare glimpse into the personal effects of one of the wealthiest men aboard the ill-fated liner. Astor, a real estate magnate and heir to one of America’s most prominent fortunes, carried the elegant timepiece — crafted by Patek Philippe and retailed by Tiffany & Co. — during what would become his final journey.
Made of 18-karat yellow gold and engraved with Astor’s monogram, it reflects the understated sophistication of the Gilded Age elite. Accompanying it is a 14-karat gold pencil case, a small but telling accessory that speaks to an era when even the most utilitarian objects were elevated through fine craftsmanship. Together, they were among the items recovered from Astor’s body days after the Titanic slipped beneath the waves in April 1912.
The backstory adds a deeply human dimension to these glittering relics. Astor, 47 at the time, was traveling with his young second wife, Madeleine Astor, who was just 18 and pregnant. Their marriage had stirred intense public scrutiny due to their age difference, prompting an extended honeymoon abroad.
When the Titanic struck an iceberg, Astor ensured Madeleine’s safety, helping her into a lifeboat. He famously asked if he could accompany her due to her “delicate condition,” but was denied under the “women and children first” protocol. Witnesses recall him calmly stepping back, kissing his wife goodbye and promising, “I’ll see you in New York.” He never made it.
According to Freeman's, the 18-karat gold pocket watch was purchased by Astor from Tiffany & Co. in New York in 1904. After the Titanic disaster, the watch and pencil were returned to Astor's son, Vincent Astor, who wore the watch throughout his life until his death in 1959. The watch subsequently passed through successive generations of the family:
What makes this upcoming sale particularly intriguing is the high-profile existence of another “Astor watch.” In April 2024, British auction house Henry Aldridge & Son sold a 14-karat gold Waltham pocket watch — also attributed to Astor — for a staggering $1.485 million, setting a record at the time for Titanic memorabilia.
Official recovery records from 1912, however, indicate that only one watch was found on Astor’s body.
That discrepancy has sparked ongoing debate in the auction world. Freeman’s maintains that its Patek Philippe example holds the strongest claim to authenticity, citing uninterrupted ownership within the Astor family for more than 120 years, along with archival documentation. The competing watch, while undeniably historic, followed a more circuitous path through private hands.
In the lead-up to the 2024 auction, Henry Aldridge & Son recounted how the real estate magnate’s possessions were turned over to Astor’s son, Vincent, who had the gold watch completely restored. Vincent reportedly wore the watch regularly, but in 1935, presented it as a christening gift to the infant son of William Dobbyn IV, John Jacob Astor’s executive secretary and confidant. The watch would remain in the Dobbyn family until it was auctioned in the late 1990s.
Credits: Auction items, Astor photo and newspaper front page courtesy of Freeman’s. Photo of John Jacob Astor IV and his wife, Madeleine, circa early 1910s. Public domain, via Wikimedia Commons.
