He continued the struggle to keep the paper ahead of its debts, often printing pleas to his advertisers and subscribers to pay their bills any way they could.
On Juneau's request, O'Rourke's associate Harrison Reed remained to take over the Sentinel's operations. A deathly ill O'Rourke struggled to help the paper to find its feet before he died six months later of tuberculosis at the age of 24.
It was first published as a four-page weekly on June 27, 1837. The founder of Milwaukee Solomon Juneau provided the starting funds for editor John O'Rourke, a former office assistant at the Advertiser, to start the paper. The Milwaukee Sentinel was founded in response to disparaging statements made about the east side of town by Byron Kilbourn's westside partisan newspaper, the Milwaukee Advertiser, during the city's "bridge wars," a period when the two sides of town fought for dominance. The merged paper's volume and edition numbers follow those of the Journal. Grant listed below their respective newspaper's flags. The legacies of both papers are acknowledged on the editorial pages today, with the names of the Sentinel's Solomon Juneau and the Journal's Lucius Nieman and Harry J. 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." In early 2003, the Milwaukee Journal Sentinel began printing operations at its new printing facility in West Milwaukee. The new Journal Sentinel then became a seven-day morning paper. The Journal Sentinel was first printed on Sunday, April 2, 1995, the result of the consolidation of operations between the afternoon Milwaukee Journal and the morning Milwaukee Sentinel, which had been owned by the same company, Journal Communications, for more than thirty years.
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