He worked as a clerk at the Manufacturers Hanover Corporation for a year and a half and then for a similar period as a department store salesman at Abraham & Straus, a Macy's rival.

He moved his family into the topmost two floors, a seven-bedroom duplex with terraces, a thousand-square-foot library, and a baronial stone fireplace.

[11] According to a biography in the Straus family newsletter, he "felt that Judaism was a religion, not a nationality, and that Jews, and members of all religious groups in any country, should assimilate....He refused all traffic with the Zionists and rigidly opposed pro-Jewish discrimination at Macy's.

First he gave away one fourth of his Macy's stock, paying far less tax than had the shares remained part of his estate.

Then on July 31, 1934, he revised his 1933 will to remove a list of gifts to 18 educational and charitable institutions because:[13] The present Federal and State estate tax laws impose substantially increased tax burdens upon the estates of decedents and may under certain conditions cause undue hardship and financial sacrifice and loss resulting from untimely sale and liquidation of assets of estates to provide for the payment of such taxes.

Under the circumstances now existing, I deem it advisable to cancel and revoke the bequests made by me...in my [earlier] last will and testament.His widow died in 1970 at the age of 94.

[15] New York City's PS 199, the Jesse Isadore Straus School on West 70th Street, is named after him.