During the second half of the 19th century, a Prussian immigrant named Otto Paul Holstein operated a drug store at 46 South Water Street in Philadelphia. Advertisements list the established year as 1849, but a passport application indicates that Holstein arrived in May 1855. On August 6, 1885, his daughter Pauline married Franz Heinrich Fleer, an immigrant from Westphalia. Fleer joined the O. Holstein family business and established the Frank H. Fleer & Co. Inc. as a confectionary company.

In 1888, Otto Holstein travelled through Europe to procure supplies of almonds, gelatins, and lemon oils. Frank Fleer and his younger brother Robert found early success selling Guru-Kola Gum and Pepsin Gum as digestive aids. Inspired by Jordan almonds, Robert added a thin candy coating to pieces of chicle gum. The name "little chiclets" was first used on October 1, 1899, and a patent was registered on February 23, 1904. Fleer introduced the Chiclets brand in the spring of 1904, and the crunchy peppermint combination was a nationwide hit. The factory on Hamilton Street was expanded after the first 60 days of sales.

In 1906, Fleer developed an unsuccessful bubble gum called Blibber-Blubber. The product was abandoned due to the concoction being too sticky. The bubbles splattered and sometimes required a solvent to remove.

 Chiclets sales continued to rise. In 1908, an additional Fleer factory was constructed in Toronto. On June 19, 1909, Frank Fleer and four other gum manufacturers formed a $6.7 million trust called Sen-Sen Chiclet Company.

In December 1913, Fleer left the Sen-Sen board and established the Frank H. Fleer Corporation with $150,000 in capital. In 1914, Sen-Sen Chiclet Company and the Chiclets brand were absorbed by the American Chicle Company. Frank H. Fleer died of a stroke on October 31, 1921. Fleer business operations were led by son-in-law Gilbert Mustin.

From 1886–1930, trading cards were commonly packaged with tobacco products, caramels, or other candies. Baseball cards were first sold with chewing gum in 1888 by G&B Gum in New York and H.D. Smith & Co. in Cincinnati. In 1923, Fleer advertised a set of 120 "famous person" strip cards. One card was included with every five-cent pack of peppermint flavor Bobs and Fruit Hearts chewing gum. The heart-shaped gums were similar to Chiclets.

The 1923 Fleer cards are listed as E241 in The American Card Catalog. The set is comprised of five different strip card series. Each card panel is printed with a Frank H. Fleer advertisement on the back. A complete set of 120 Fleer cards has not been documented. Based on observations of uncut W500 sheets, it is estimated that only 110 different Fleer cards were actually distributed.

The 60 baseball player images are identical to the strip series known as Baseball Drawings (W515-1). The Fleer set includes a 10-card strip of U.S. presidents catalogued as President Drawings (W562), plus a subset of 10 boxers, 10 Old West heroes, and 20 movie stars. Identical images appear on sheets referred to as Three Line Text Color Strip Cards (W-UNC). Several cards feature illustrations based on photographs copyrighted by Underwood & Underwood.

In August 1928, Fleer accountant Walter E. Diemer successfully refined a bubble gum formula using latex and pink food coloring. Pink was the only abundant color available and Diemer did not patent the recipe. According to Diemer, ''I was doing something else and ended up with something with bubbles.''

Market testing for the new bubble gum began on December 26, 1928. Diemer personally taught shopkeepers and salesmen how to blow bubbles. Dubble Bubble Gum debuted in 1930 and sales for the one-cent chew exceeded $1.5 million in the first year. A series of six comic strip wrappers featuring "Dub and Bub –The Dubble Bubble Twins" was copyrighted on September 20, 1930. The original black and-white comics were created by Herbert D. Seuat.

The first bubble gum cards began appearing soon after the introduction of Dubble Bubble. In 1930, Fleer released a series of 16 die-cut discs as premium prizes with Whiz Bang gum. The "Taka-Flyer" disc set features film actors and three Hall of Fame baseball players: Goose Goslin, Lefty Grove, and Gabby Hartnett.

In 1935, Fleer released Cops and Robbers Gum (R35), a 35-card set that included sticks of Dubble Bubble with each pack. The card tabs could be exchanged for a premium detective badge.

By 1937, Blony bubble gum from Bowman's Gum, Inc. dominated the market. Bowman claimed more than 60% of penny gum sales in America, a figure disputed by Fleer sales manager William B. Hunt.

During World War II, latex and chicle supplies were diverted to the defense effort, sugar was being rationed to households, and paper scrap drives were held to salvage pulp. American Chicle, Beech-Nut, Leaf, Walla Walla, and Wrigley were contracted by the government to supply gum for military rations. After D-Day, gum from American and Canadian soldiers became widely popular throughout the Netherlands.

The Japanese occupation of the Malay peninsula cut off the crucial supply of jelutong latex. Fleer was forced to temporarily suspend production of Dubble Bubble in April 1943 until 1950. Limited shipments were sent to dentists and drug stores. Legends of street prices reaching $1 per piece have been reported. In 1946, Fleer purchased a larger factory from the War Assets Corporation located on North 10th Street in Olney, Philadelphia.

A new comic strip character named Pud was introduced in 1950. In 1968, Dubble Bubble printed the one-thousandth comic wrapper.

-

Bazooka bubble gum was introduced by Topps Chewing Gum in July 1947. Bowman Gum, Leaf, Topps, and Swell released baseball card sets in 1948. An aggressive competition arose over the image rights for professional athletes. In 1956, Topps acquired the Bowman brand and player contracts for $200,000.

In 1959, Fleer released an 80-card series showcasing Ted Williams. The exclusive deal removed the popular slugger from Topps sets. Fleer followed with an Indian series and a 96-card set for The Three Stooges. In 1960, Fleer released cards for the American Football League and a throwback series of retired Baseball Greats. At the time, Topps held exclusive rights to the National Football League and about 400 Major League Baseball players. In order to compete, Fleer offered athletes $125 for a non-exclusive contract. In June 1961, Newsweek reported the bubble gum business was worth an estimated $30 million per year and Topps sales accounted for nearly half.

 

By 1964, Topps had signed nearly every active baseball player with around 6,500 exclusive contracts. In 1966, Topps forced the Exhibit Supply Co. (ESCO) to stop printing contracted players. In April 1975, Topps refused to license a series of baseball stickers and Fleer filed antitrust charges. On June 30, 1980, the court ruled that Topps had unfairly restrained trade in the baseball card market. Fleer was awarded $1 million in damages, which was tripled to $3 million under antitrust laws.

The U.S. Court of Appeals overturned the decision in August 1981. The Topps contracts contained exclusive rights to baseball cards sold with gum or candy, so Fleer simply packaged cards with team logo stickers. Donruss released a 1981 series that included a cardboard puzzle of Babe Ruth.

Topps filed unsuccessful lawsuits against Fleer in 1982 and 1986 before capitulating. The end of the two-decade baseball card monopoly allowed new companies Score and Upper Deck to enter the market. Topps stopped including gum with baseball cards after the 1991 series.

Fleer included a stick of Dubble Bubble inside each pack of basketball cards from 1986–1989. Initially a sales flop, the 1986–87 Fleer NBA Basketball series is now sought after for containing the Michael Jordan rookie card and other hall of fame inductees. In 1989, Gilbert Mustin Jr. sold Fleer to Charterhouse Equity Partners for $75 million. The Charterhouse deal was led by former Donruss executive Paul Mullan.

Impel Marketing Inc. was formed as a subsidiary of Brooke Group Ltd. on June 21, 1990. In October 1990, Impel released the first Marvel Universe trading cards, a popular series featuring hologram chase inserts. Similar sets followed for Walt Disney and DC Comics characters. Impel licensed various non-sport properties including A Nightmare on Elm Street, G.I. Joe, Star Trek, and Terminator 2: Judgement Day. The first sports release was from Impel was the 1990–91 Inaugural Edition of SkyBox NBA Basketball Cards.

"Marvel to buy Fleer." Wizard, vol. 1, no. 14, October 1992, p. 12.

“Marvel to buy Fleer for $265 million.” United Press International, 24 July 1992.

“Marvel to buy rival trading-card maker.” New York Times, 10 March 1995. p. D3.

"New Corporations." Oil, Paint and Drug Reporter, vol. 84, no. 27, 29 December 1913, p. 63.

Official Gazette of the United States Patent Office, vol. 108, United States Patent Office, 23 February 1904, p. 2136.

“O. Holstein, Importers of Mexican Vanilla Beans.” Oil, Paint and Drug Reporter, vol. 36, no. 8, 21 August 1889, p. 46.

Shamus, Gareb. "A Talk With President Frank O'Connell." Wizard, vol. 1, no. 11, July 1992, pp. 18–21.

Taylor, Ted. “Fleer/SkyBox Sale Finally Goes Through.” Philadelphia Daily News, 4 February 1999.

Taylor, Ted. "Time To Turn Out The Lights At Old Fleer Factory." Philadelphia Daily News, 25 January 1996.