In September 2006, the Journal Sentinel announced it had "signed a five-year agreement to print the national edition of USA Today for distribution in the northern and western suburbs of Chicago and the eastern half of Wisconsin".

[5] On Juneau's request, O'Rourke's associate, Harrison Reed, remained to take over the Sentinel's operations on behalf of Democratic Party politician James Duane Doty.

Fillmore employed a succession of editors, including Jason Downer, later a Wisconsin Supreme Court justice, and Increase A. Lapham, a Midwestern naturalist who later helped establish the National Weather Service.

When the adopted constitution fell short of Whig expectations, the Sentinel was instrumental in encouraging its rejection by territorial voters on April 6, 1847.

The Sentinel launched a German-language paper, Der Volksfreund, to bring the city's large population of German immigrants to the Whig cause.

The war also resulted in a shortage of skilled printers, so in 1863 the Sentinel began hiring and training "female compositors" to typeset the paper, albeit in another building away from the men.

Bascom had earlier offered Turner a position teaching elocution at the university that he turned down in favor of working for the Sentinel for nine more months.

[15] In 1892–1893 the Sentinel moved temporarily from its home on Mason Street so that the old building could be torn down and a new, state-of-the-art structure could be erected in its place.

The Sentinel joined in the chorus of indignation that resounded from Milwaukee and beyond, particularly during 1899 when Pfister and Payne succeeded, by means of bribery, to push through a 35-year contract with the city.

On December 29 Pfister and Payne sued the Sentinel for libel, to which the paper replied that it had fallen prey to "probably the most formidable and influential combination of selfish interests ever found in the city of Milwaukee.

"[16] Rather than going to trial and having his business practices revealed, Pfister bought the Sentinel outright on February 18, 1901, paying an immense sum to buy up a majority of its stock.

During La Follete's successful re-election campaign in 1902, Pfister's political power was diminished after it had been revealed that he had secretly purchased the editorial pages of some 300 of the state's newspapers.

Edna Ferber, later a famed writer and Pulitzer Prize-winning novelist, was a Milwaukee Journal reporter for nearly four years, from approximately 1903 to 1907.

[26] On April 8, 2016, decades of local ownership for both papers ended when Journal Media Group was acquired by the Gannett Company for $280 million.

[3] Gannett owns most of the daily newspapers in the central and eastern parts of Wisconsin (eleven in all),[27] including the Green Bay Press-Gazette and Appleton's The Post-Crescent.

[28] The Journal Sentinel also collaborates with the Press-Gazette for Packers coverage, and adapted to Gannett standards, including newspaper layout, website and apps, in August 2016.

[30] By 2021, it was reported that about 90% of Journal Sentinel subscriptions were for its print edition despite a years-long push to increase the number of digital subscribers.

[37] In 2011, Mark Johnson, Kathleen Gallagher, Gary Porter, Lou Saldivar, and Alison Sherwood were awarded the Pulitzer Prize for Explanatory Reporting for their "lucid examination of an epic effort to use genetic technology to save a 4-year-old boy imperiled by a mysterious disease, told with words, graphics, videos and other images.

At the Journal Sentinel's request, the Milwaukee Public Library loaned decades of missing microfilm volumes to complete the digitization.

[40] Newsbank unsuccessfully attempted to sell Journal Sentinel digital archive access to the Milwaukee Public Library, which could not afford their asking price.

The Library already subscribed to Newsbank's obituary and recent Journal Sentinel articles, as well as other proprietary databases with annual subscriptions costing less than $100,000.

The newspaper changed ownership to Gannett in April and by August had requested that Google remove free public access to the archives, leaving a gap in coverage.