US Congressman, Mayor of Chicago, Illinois. Nicknamed "Long John" for his six-foot six-inch frame, he served as a Democrat in the US House of Representatives from the Illinois 4th District from 1843 until 1851, from the Illinois 2nd District from 1853 until 1855, and as a Republican from the Illinois 1st District from 1865 until 1867. He also served two terms as the Mayor of Chicago, Illinois from 1857 until 1858 and again from 1860 until 1861. He received his education at the New Hampton Literary Institute (now New Hampton School) in New Hampton, New Hampshire and at the academy of Dudley Leavitt in Meredith, New Hampshire. He then attended Dartmouth College at Hanover, New Hampshire, graduating in 1836. That same year he moved to Chicago, Illinois and became the managing editor of Chicago's first newspaper, the Chicago Democrat, and eventually became its owner and publisher. After starting a law practice and entering politics, he became a business partner of Illinois financier Jacob Bunn, and they were two of the incorporators of the Chicago Secure Depository Company. After aligning himself with the Jacksonian Democrats, he was elected to Congress, where he served for a total of six terms, five of them as a Democrat. After completing his 5th term in Congress, he returned to Chicago and switched political allegiance to the Republican Party, and was elected Mayor of Chicago for two two-year terms in 1857 and 1860. In 1861 he closed his newspaper and in 1864 he ran again for Congress as a Republican, and was elected for his last term, serving from 1865 until 1867. During this term, there was a controversial vote to settle a boundary issue between Wisconsin and Illinois, with Wisconsin claiming land as far as the tip of Lake Michigan. He was promised that if he voted to give the land including Chicago to Wisconsin, he would be appointed to the US Senate but he rejected the offer. After leaving Congress in 1867 he retired to his home in Chicago. He researched and wrote "The Wentworth Genealogy - English and American" twice, which he published privately. He died at his home at the age of 73. His obelisk is the tallest marker in the cemetery.