[8] A lifelong Republican and supporter of Lincolnism,[9] by the time the Civil War broke out in 1861, Segar publicly espoused views sympathetic to the abolition of slavery: “The everlasting hills do not more firmly cling to their base, than do I to these, my opinions, against secession, and to my resolve, now herein repeated before God and man, to stand by them now and forever.

I am thus explicit, that there may be no misunderstanding between me and those whose suffrages I stand for.” By the close of the war, he was calling slavery “one of the greatest evils that ever afflicted and cursed [the United States].”[10] Along with a partner, Segar purchased half of the original Hygeia Hotel near Fort Monroe at Old Point Comfort for $90,000 and ran it for several years, making Caleb C. Willard a co-owner and administrator of operations in 1859 for the sum of $15,000.

[11] In October 1862, the United States government deemed the Hygeia Hotel inconvenient to the operations of the Army at Old Point Comfort, and it was demolished, without any compensation to Segar or Willard.

[13][14][15] Most of the time it involved official business, although occasionally it was personal, like on January 24, 1862 when, as a gift, Segar sent a crate of terrapins to the White House for Lincoln to consume.

[18] On May 24, 1861, the levying of the historic Contraband Decision occurred near the gates of Segar’s farm, in the area known at the time as the Fort Fields (present-day County Street in Phoebus at the Hampton National Cemetery).

In the coming weeks and months, this decision initiated a mass exodus of enslaved people seeking freedom behind Union lines at Segar’s property and at Fort Monroe.

[20] As a result, the farm and the surrounding area not only acted as a Union encampment but also became one of the first freed Black communities in the South, known as Sugar Hill.

[22] Segar presented credentials as a Unionist Member-elect to the Thirty-seventh Congress from an election held on October 24, 1861, but the House on February 11, 1862, decided he was not entitled to the seat.

Segar presented credentials on February 17, 1865, as a United States senator-elect to fill the vacancy in the term commencing March 4, 1863, caused by the death of Lemuel J. Bowden, but was not permitted to take his seat.

Camp Hamilton and its operations wiped clean the resources of his farm, and the burning of the town of Hampton, Virginia destroyed all of the Elizabeth City County courthouse records, leaving Segar unaware of who owed him money and to whom he was in debt.

Through the early 1870s, Segar continued to seek compensation for his losses through the Southern Claims Commission, which adjudicated requests from loyal Unionists who suffered property damage during the conflict.

In his petition to the Southern Claims Commission, Segar recounted his loyalty and described the extensive sacrifices his land and resources had made to support the Union cause.