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An Old Mystery: Why Did Jacob Ruppert Leave a Fortune to an Unknown Woman?

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This was inspired by something I discovered while researching an article on the 1939 Yankees from a year ago (I procrastinated). Owner Jacob Ruppert, who died in January of '39, left a third of his estate to a completely unknown woman. It sparked an investigation of sorts into discovering who she was and why he did this (both for the 1939 press and for myself when I found out).

Colonel Ruppert was integral in building the Yankees into a perennial winner. He bought the team in 1914 (for about $450K) and within years had acquired Babe Ruth and other stars, and had turned the upstart ball club into the one rich in history we now think of.

Ruppert's estate was valued between $20 and $80 million at his death. For the sake of brevity, let's average that and say it was worth $50 million. That equates to about $800 million today. (Funny, because that wouldn't even buy half of the 2011 Yankees.)

Then, upon his death, came this story -

UNKNOWN GIRL IS NAMED IN RUPPERT WILL - New York, Jan. 20 [1939] - A young and comparatively unknown woman, Helen Winthrop Weyant, was named as one of the three chief beneficiaries of Col. Jacob Ruppert, owner of the New York Yankees.

The other two-thirds were left to two of his nieces.

I was determined to find out more about Helen Weyant. Searching through old newspaper articles, I happened upon a handful about this woman. It turns out she came to New York City from Massachusetts looking for a career on Broadway.

At first I assumed she was Ruppert's mistress. A 71-year-old man leaving a vast chunk of money to a 37-year-old actress/singer? C'mon.*

* It also made me think of Susan Alexander in Citizen Kane, and how "he was going to take the quotes off the 'singer.'"

But I was wrong to assume Ruppert had an affair with her. For one, he was never married, so if they did have a physical relationship, it would've been perfectly legal.

So who was she?

Ruppert never had any children either, so it made sense for him to have a personal relationship with someone. Why not a young, attractive show-girl?

Helen Weyant used an alias on Broadway; she was known as "Winthrop Wayne" as a chorus girl, and hailed from Winthrop, Mass., using her hometown as her last name. Like Ruppert, she also never married.

She liked baseball but did not consider herself a fan. Weyant wasn't "particularly excited" about owning a third of the Yankees and wanted nothing to do with actually running the ball club.

She met him 14 years prior to his death, when she was 23 and he was 57; she didn't want to define their relationship, but eventually said that it was "like a father and daughter."

So I'm still left with the question of whether they were just friends, or considerably more. What's your take?


- I especially like this sentence about Ruppert from one of the articles: "... the man whose liberality hiked baseball salaries to their present high level." Sound like a more recent owner?

- Weyant was the daughter of Ruppert's friend, George. Her brother, Rex, was the Yankees "assistant to [the] road secretary." That sounds awfully like "assistant to the traveling secretary," no?


Ed Barrow: The Bulldog Who Built the Yankees' First Dynasty

The Florence Times [Florence, Alabama]

The Telegraph-Herald [Dubuque, Iowa]

Youngstown Vindicator [Youngstown, Ohio]