At the beginning of the Depression, he was asked by J.P. Morgan & Co. to turn around the failing Montgomery Ward and succeeded in restoring its profitability by making huge changes.

"[2] In the postwar years, however, he failed to take advantage of the demand for durable goods and did not expand Montgomery Ward, costing it prominence in the retail field.

[8]By making the company become profitable, Avery earned great wealth in the process through significant stock options.

[9] His strong control and caution worked against him as the company began to recover in the mid-1930s, when he might have allowed some expansion, but he believed the economy too fragile.

[9] As president of the Commercial Club of Chicago, Avery supported Julius Rosenwald's idea for an industrial museum as early as 1925.

[11] Avery endowed several professorial chairs at the University of Chicago, and he financially supported research and expeditions of the Field Museum of Natural History.

[14] He resisted signing a contract after a union had won representation for 7,000 of Montgomery Ward's employees until twice ordered by Roosevelt.

[15][16][17] Avery yelled at the Attorney General, who had flown to meet with him and try to avert a showdown, "To hell with the government, you... New Dealer!

Unlike Sears, Avery resisted pension plans, insurance and profit sharing with employees; he refused to spend money on company expansion.

[21] In late 1946 or early 1947, Avery gave 100% of the copyrights of Rudolph the Red-Nosed Reindeer, a story his employee Robert Lewis May had written in 1939 for a company promotional assignment, back to May.

During the time between 1939 and 1947, the story had quickly become a popular part of Montgomery Ward's annual promotional campaign, with over six million copies given away.

Avery's relinquishment of the copyrights from Montgomery Ward to May resulted in May immediately publishing the story commercially for the first time as a popular children's book, and later, having his brother-in-law, songwriter Johnny Marks, create a song based on it, becoming one of the best selling songs in history.