The Preston-Woodward correspondence consists of 45 letters written by Paul S. Preston to Jackson Woodward and 2 letters written by Woodward to Preston, spanning 1845-1858. Both men were lawyers in Wayne County, Pennsylvania, and their correspondence primarily contains discussions of various political issues and public figures of the time, both national and local, though a few earlier letters touch on pastimes, such as fishing and cigar-smoking. The tone of the correspondence is frequently scathing and humorous, as in Preston's 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 letters by Preston 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."