Milton Holland was born in Austin, Texas, on August 1, 1844 to Bird Holland, a white civil servant, and Matilda Unk, an enslaved African American woman whom Bird owned. Holland had two brothers, William and James, and two sisters, Kate and Eliza. In the early 1850s, Bird freed his three sons so they could receive a formal education at Albany Manual Labor Academy in Athens County, Ohio. While there, Holland learned to craft shoes, studying as an apprentice to a local shoemaker.
When the Civil War began, Holland yearned to enlist and serve in the Federal Army. At first, he was ineligible due to his age, so he found work making shoes for the Army. But Holland reapplied on September 2, 1862, after he had turned 18, but this time he was denied due to his race. Undeterred, Holland became a personal servant for Ohio politician Nelson Van Vorhes, who served in the Army. By June 1863, less than a year after his second enlistment attempt, the Federal Army reversed its stance on excluding Black recruits. Holland joined the newly formed 5th Regiment, US Colored Troops, which was a segregated unit of African American soldiers. He fought in several notable military campaigns, including the Battle of the Crater in July 1864. But his biggest victory was yet to come.
Leading the Charge
On September 29, 1864, Holland and his company were fighting at New Market Heights, Virginia, near the Confederate capital, Richmond. Penetrating the fortifications proved difficult, and the company suffered extensive damage and numerous casualties. Looking around, then-Sergeant Major Holland suddenly realized that every single officer was dead or severely wounded. Without hesitation, he courageously took command of the unit, urging his brothers in arms to continue the fight. His fearless leadership and fighting spirit encouraged the company to relentlessly pursue the enemy. Although Holland was wounded, he and the troops pulled off a memorable victory.
One of Holland’s superiors, General Butler, wrote the War Department an official recommendation that Holland be awarded the Medal of Honor for his selfless service and valiant efforts during the Battle at New Market Heights. He urged the office to promote Holland to captain and to give him a proper captain’s commission. Although Holland received the promotion, the War Department denied him the commission due to his heritage. On April 6, 1865, Holland was awarded the Medal for his heroic actions during the prior year, making him the first African American Texan to earn the prestigious honor.
Living a Life of Public Service
Following the war, Holland returned to Ohio; he married Virginia Dickey on October 24, 1865. For a few years, he took up his former work as a shoemaker. But Holland had bigger dreams. He aspired to be a lawyer who provided fair representation — and earned justice — for other African Americans. After Holland moved to Washington, DC, in 1869, his friend, John Mercer Langston, assisted him in landing a clerkship in the US Treasury Department. Holland then balanced his full-time job with studying law at Howard University. When he graduated in 1872, he was the only Texan in his class of 17.
Holland practiced law for a few years, and became one of the inaugural African American attorneys to practice in front of the Supreme Court. But by 1887, he had turned his attention to banking and insurance. He served in leadership roles for two Black-owned organizations, and later founded his own insurance company, called Alpha Insurance, in Washington, DC.
Holland never gave up speaking out for Black individuals and their rights. In fact, a newspaper, The People’s Friend, included him among some of Washington DC’s most honorable men speaking emphatically about African American issues in America. Some have even compared him to famous activist Frederick Douglass. Holland’s legacy of humble service and passionate leadership in the face of adversity remains a powerful inspiration.
