Judson left the business in 1898 for the National Biscuit Company where he had a long and well-regarded career in bakery management.

In 1888, he joined Vanderveer and Holmes Biscuit Company,[8] and he had become a salesman traveling internationally[9] for this cracker business by 1894.

[10] He was traveling in England on business in 1893–94[9] when he observed commercially baked fine cakes sold in grocery stores, and he was inspired to bring the idea to America.

[11] By March 1898, retailer ads featured Drake's pound cakes by brand name in various flavors.

[12] In 1900, retailer ads featured Drake's layer cakes with chocolate or vanilla icing at 18 cents.

Drake's Famous Loaf Cakes continued to sell under that brand name at least to December 30, 1902.

The firm was noted as having been the first to have produced cakes in large quantities for grocery stores, which must reference the origins of the Harlem bakery.

[24][25] A photograph of the fourteenth annual dinner in 1917, captures the grandeur of the event held at Silsbe and Son Oyster Bar and Chop House in Manhattan (established 1863),[26] with attendees in suits, custom menus on the tables, tuxedoed wait staff, and lavish décor.

[32] In May 1913, Drake Brothers announced that they would build a new five story bakery built of brick and concrete on Clinton Avenue in Brooklyn on a lot 80 by 125 feet.

Joseph Gross, a German immigrant who came to the U.S. in 1898 and worked as striper painting lines and designs on horse wagons and automobiles, drew the original Drake's logo which consisted of a duck with a chef's hat holding a tray of cakes.

[42] The preferred shares of Drake Bakeries, Incorporated were owned by Bessemer Investment Company,[43] the investment arm of the Bessemer Trust which was founded in 1907 by Henry Phipps from proceeds from the sale of Carnegie Steel, which Phipps founded with Andrew Carnegie.

[43] In 1925, Drake Bakeries advertised with full page ads a new freshness policy where they would remove products from store shelves after 48 hours.

[48] One of the top sellers for Drake's still today, Devil Dogs, was filed for trademark protection in 1926 and shown as first sold in commerce on June 15, 1926.

[53] The Yankee Cake Company was stated as a wholly owned subsidiary of Drake Bakeries in a 1941 article.

[28] On August 28, 1928, Drake Bakeries was purchased by acquisition of common stock by Central Distributors, Inc. Central Distributors was formed March 9, 1928, by Ralph Ward, his cousin, William Ward, and Benjamin Titman as a holding company for food companies.

[43] In 1929, Drake begins advertising that the products are wrapped in cellophane, noting that shoppers could see what they were buying and that it was a "flavor-sealed" package.

In December 1930, Drake's Coffee Cakes, still one of the top-selling products, came on the scene in newspaper advertisements that mentioned a radio broadcast that offered to share the recipe.

[57] In 1941, in addition to the aforementioned Brooklyn, Boston, Irvington, NJ, and Providence, bakeries, the Philadelphia branch is noted as well as two distribution points in the Bronx and Jamaica (Queens) in an article.

[60] During World War II, Drake's production was limited due to rationing of sugar and shortening.

[67] On April 18, 1962, Drake Bakeries had a case heard in front of the United States Supreme Court.

[74] On July 1, 1986, Borden announced the sale of Drake Bakeries to Ralston Purina Co. to be part of their Continental Baking Co.

[41] If the purchase price was proportional to sales, Interstate may have paid in the neighborhood of $80 million for Drake Baking.

[86] During the fall of 2017, and without warning to consumers, McKee stopped production and distribution of Drake's Coffee Cakes.

[87] Drake's Coffee Cakes are mentioned in the season 3 episode of the NBC sitcom Seinfeld titled "The Suicide", which aired on January 29, 1992.

[89] Yodels are referenced in the season 4 episode of the CBS sitcom Everybody Loves Raymond titled "Robert's Rodeo", which aired on February 7, 2000.

Drake's Devil Dogs are mentioned in the season 4 episode of the HBO series The Sopranos titled "The Weight", which aired on October 6, 2002.