The Preston-Woodward correspondence contains letters written to Jackson Woodward by Paul S. Preston and business letters addressed to Woodward. The earliest items in the collection relate to Nathaniel A. Woodward of Bethany, Pennsylvania. Of these early letters, two from 1836 (also addressed to Jacob Faatz and Lucius Collins) discuss the election of delegates to amend the Pennsylvania state constitution and, to a lesser extent, national politics prior to the 1836 presidential election. The bulk of the collection pertains to Jackson Woodward, a lawyer from Honesdale, Pennsylvania, including incoming business-related correspondence and a personal letter from his brother, W. Woodward. Of particular interest within the collection are 58 letters composed by Paul S. Preston, as well as two by Jackson Woodward, discussing contemporary politics and prominent national and local political figures. Preston, who lived in Stockport, Pennsylvania, often took a scathing and humorous tone, as in his letter of November 29, 1845, in which he claimed that "since the day that the iron willed Tennessean, your illustrious namesake [Andrew Jackson] dressed despotism in the garb of Democracy, there is very little difference between an Emperor and a President."
A number of Preston's letters criticize the Locofocos, a radical wing of the Democratic Party founded in 1835 to protect the interests of workers and oppose monopolies and tariffs. Preston frequently characterized them as hypocritical, as in a letter of February 18, 1847, in which he compared the high salaries paid to Locofocoism's "panderers" and low wages earned by American soldiers fighting in Mexico. Preston also praised the Whig generals in the Mexican-American war as aggressive fighters (October 28, 1847), and included political poetry in several of his letters. His letter of January 2, 1850, contains a humorous petition in verse. Scattered letters concern presidential and midterm elections, and a lengthy letter of January 22, 1851, compares the attitudes of Yankees and Southerners, offering the opinion that the Southerners underestimate their dependence on slaves. On January 7, 1851, Preston criticized the Fugitive Slave Law and expressed his unwillingness "to be turned into a hound to run down a runaway negro."
Although the letters provide a much clearer picture of Preston than Woodward, the two men seemed to have held differing opinions on many issues, including slavery. In one of the two items he wrote, dated September 23, 1852, Woodward defended the Fugitive Slave Law and called abolitionism a "most mischievous, damnable doctrine."