In October 1864, Thomas Savage, the Vice Consul to Cuba, sent $350 to Secretary of War Edwin Stanton. Savage collected this money from several American citizens living in Havana who wanted it donated to the "noncommissioned officer or private, who may be first to enter Richmond, should that City be taken by assault, and in the event of his being killed, to his legal heirs."

Stanton deposited the money inside the City Bank of New York. He then sent a written communication to Lt. Gen. Ulysses S. Grant. As commander of the Union forces near Richmond, Grant had the authority to determine who should receive the prize money. As the months passed, more patriotic northerners heard about the "First-to-Enter-Rich" prize fund and contributed to it. By April 1865, the prize fund had grown to $460.

April 1 and 2, were crucial days in the Army of the Potomac's advance. A Union army force under Maj. Gen. Gouverneur K. Warren attacked the far-right flank of Gen. Robert E. Lee's line at Five Forks crossroads in Virginia on April 1. As a result, the 5th Corps troops struck a section of an embankment occupied by Maj. Gen. George Pickett although all of 5th Corps participated in this assault, Col. Richard N. Bowerman's Maryland Brigade, bearing 875 enlisted men, had the good fortune of being the first to overrun Pickett's entrenchments.

Ultimately, the Marylanders routed Brig. Gen. Matthew Ransom's brigade, with only ten dead, 57 wounded, and 11 missing. In addition, the Marylanders captured two battle flags and dozens of prisoners during the engagement. Among those receiving recognition was Corporal Jacob R. Tucker of Company G, 4th Maryland Volunteer Infantry. Several brigade members claimed he had been the first to cross the enemy parapet. Tucker was not a native of Maryland, having been born in Chester County, Pennsylvania. However, he enlisted in Baltimore in 1862, mustering into the Army on August 13. Despite his young age, Tucker had survived a wound during the Battle of Spindle Farm, Virginia. Interestingly, Tucker turned 20 years old on April 1, 1865.

A second Marylander distinguished himself the following day. The 6th Corps of Maj. Gen. Horatio G. Wright struck Lt. Gen. A. P. Hill's Confederate corps southwest of Petersburg at dawn on April 2. 14,000 federal troops overran these Confederate earthworks, breaking open a gaping chasm in the Confederate line. The 6th Maryland, led by Col. Joseph C. Hill, occupied a portion of the front line. Even though there was a later debate over which Division made first contact, most officers in the 3rd Division, 6th Corps, believed Hill's regiment crossed the enemy earthworks first. Following the battle, Colonel Hill identified twenty-two officers and men from his regiment who distinguished themselves by being at the front of the charge. Hill identified Sergeant John Ezra Buffington of Company C, 6th Maryland Volunteer Infantry, as a member of this contingent. Buffington was a farmer from Taneytown, born July 12, 1839. Like Tucker, Buffington enlisted in Baltimore during the summer of 1862.

Lee's Army began a desperate evacuation of Petersburg and Richmond once the lines outside Petersburg had been taken. As a result, Lee's Army was trapped at Appomattox Court House, and Jefferson Davis was captured by Union soldiers near Irwinville, Georgia, one month later. These attacks sounded the death knell for the Confederacy on April 1 and 2.

Following the surrender of the other major Confederate armies, Grant identified which of his soldiers was to receive $460 in prize money. Given Richmond not falling directly from the attack, he awarded the money to several soldiers who led the way during the April 1 and 2 assaults. In the end, he divided the money three ways. The 5th Corps soldier who was first to atop the earthworks at Five Forks would receive one-third of the fund. One-third would go to the soldier from the 6th Corps, who was the first to cross the earthworks southwest of Petersburg. And the final third would go to the 24th Corps soldier, who was the first to scale the forts at the far end of the Petersburg line. Grant ignored the 9th Corps for some unexplained reason, which made a bold assault south of Petersburg. Why he missed this Corps is still a mystery.

As a result, the three corps commanders - Maj. Gen. Charles Griffin (5th Corps), Maj. Gen. Horatio Wright (6th Corps), and Maj. Gen. John Gibbon (24th Corps)—began making inquiries. Eventually, they identified three soldiers. Gibbon selected Sergeant Thomas McGraw, Company B, 23rd Illinois; Griffin (who had recently replaced Warren) chose Corporal Tucker of the 4th Maryland. In nearly identical letters, both soldiers received their share of the prize money, which amounted to $153.33.

As opposed to the other two Corps, the identification process for the 6th Corps was murky. Due to the rapid strike by Union forces on the Confederate line, the officers of the 6th Corps were unable to identify which regiment was the first to penetrate the enemy line. However, Maj. Gen. Warren Keifer firmly believed his brigade had achieved the feat first. Keifer interviewed his officers, and on May 19, he decided to award the prize money to Sergeant Buffington. In a letter to his divisional commander, Maj. Gen. Truman Seymour, Keifer concluded: "I … am fully satisfied that Sergeant John E. Buffington, Co C 6th Maryland Volunteers was the first man to pass over the works … The men admit that the Sergeant did not halt upon the works but sprang within them."

Although Keifer's report was circulated up the chain of command, it did not influence the final decision. Due to some unknown reason, Maj. Gen. Horatio Wright selected another soldier, Sergeant David Young of the 139th Pennsylvania. Grant's letter to Young appeared in the Official Records of the War of the Rebellion. Like Tucker's letter, it read:

"There are still some differences of opinion regarding which soldier Buffington or Young deserved the prize money. Years later, Buffington applied to the War Department for a Medal of Honor based on his combat performance on April 2, 1865. In 1908, the War Department issued the medal. On March 28, 1908, at Reindollar's Opera House in Taneytown, a delegation from the Grand Army of the Republic (G.A.R) made the official presentation to Buffington, who was then 68 years old. A large gathering came out to witness the ceremony. The President of the G.A.R., John Rigdon King, delivered the dedicatory remarks. King was a self-selecting choice. After all, he had been present during the April 2, 1865, assault. In addition, he had served as the first lieutenant of Buffington's company. As he closed his speech, King referred to the $460 prize money, claiming, incorrectly, that Buffington had been awarded the money.

On November 22, 1924, Buffington died only 14 years after receiving his medal. He is buried at Trinity Lutheran Cemetery, Taneytown.

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