Stephen Douglas, large portrait design with "Douglas and Popular Sovereignty" slogan below, on cover to Centre Sandwich, N.H., franked with 1857, 3¢ dull red tied by sharp blue "Kalamazoo, Mich., Sep 12" cds; stamp with a few toned perfs, otherwise Very Fine, a rare design (Milgram rarity 3, 1-5 known). Scott No. 26. Milgram No. SD-9  Estimate $300 - 400. $0 (Image)

Stephen Douglas, large portrait design with McNally & Co. - Chicago publisher imprint below, on cover to Galesburg, Ill., franked with 1857, 3¢ dull red tied by circle of wedges cancel, matching "Geneseo, Ills., Sep 17" cds alongside; small cover tone spot, Very Fine, a rare type of Douglas campaign cover used shortly before the 1860 election (Milgram rarity 3, 1-5 known). Scott No. 26. Milgram No. SD-13  Estimate $300 - 400. $0 (Image)

Stephen Douglas, portrait design with Carpenter & Allen - Boston imprint below, on cover to Meredith Village, N.H., franked with 1857, 3¢ dull red tied by fancy Masonic symbol in segmented circle handstamp, matching "Holderness, N.H., Apr 6" cds, cover forwarded to Boston, Mass. with "Meredith Village, N.H., Apr 8" cds additionally tying stamp; cover slightly reduced at top, otherwise Very Fine (Milgram rarity 2). Scott No. 26. Milgram No. SD-22  Estimate $200 - 300. This cover was mailed more than two weeks before the opening of the original Democratic Convention in Charleston on April 23, 1860, which ended in a deadlock after 57 ballots. $0 (Image)

Stephen Douglas, portrait in ornamented frame with Douglas name and Ed Mendel - Cleveland imprint below, on cover to St. Louis, Mo., franked with 1857, 3¢ dull red tied by grid handstamp and "Galesburgh, Ill., Mar 12, 1861" cds, circular "Advertised" date stamp; cover scuffs and reduced at right into stamp, Fine (Milgram rarity 3, 1-5 known). Scott No. 26. Milgram No. SD-35  Estimate $150 - 200. $0 (Image)

Stephen Douglas, portrait design with eagle & flag allegories, shield containing Douglas & Johnson's names, verse at top and Raynor - New York imprint at left, on cover to Erving, Mass., franked with 1861, 3¢ rose canceled by blue grid handstamp, matching "Northfield Farms, Mas., Mar 3" cds, Extremely Fine. Scott No. 65. Milgram No. SD-39  Estimate $300 - 400. $0 (Image)