With a little over two years left to go, sagging poll numbers and House Republicans ignoring his immigration reform pleas, President Obama is signaling that he will soon take whatever actions are in his power to move immigration forward. 

Obama is speaking like a leader willing to go bold.

150 years ago this week, abolitionist activist Frederick Douglass paid his second visit to President Lincoln.  That little remembered meeting provides a fascinating window into how staring at the end of one’s time in the White House can liberate a president to do what was once politically unthinkable. 

Late summer of 1864 was a terrible time for Lincoln.  In a sweltering city crowded with wounded soldiers and a Congress losing faith he might ever end this interminable war, Lincoln was convinced he would lose reelection. This defeat would come at the hands of a candidate, General George McClellan, who would end the war with a compromise preserving slavery.

Frederick Douglass had gone to the White House the year before to demand better treatment for black Union soldiers, and he had come away from that meeting encouraged by how he had been treated as an equal and Lincoln's candid manner.  Nonetheless, a year later Douglass was criticizing Lincoln over frustrations with the president’s caution.   Lincoln was reluctant to advocate for black men to be able to vote in Union-controlled Louisiana.

Hearing Douglass’ recent harsh comments, Lincoln asked if Douglass would return to the White House, remarking that Douglass could be “the most meritorious man in the United States.” Douglass found Lincoln in an “alarmed state.” This was no jovial, story-telling Lincoln, but a man with a “heavy burden of care that weighed upon his spirit.”

Douglass was shocked when Lincoln produced a draft of a letter where he, against all previous policy, stated his openness to negotiating peace with the Confederacy. Did Douglass think Lincoln should mail it out? 

Douglass strongly advised Lincoln not to make the letter public.  He told the president that “it would be taken as a complete surrender of your antislavery policy—and do you serious damage.”  With the governor of Connecticut waiting in the next room, Lincoln then asked Douglass to stay longer, and what he proposed next shocked Douglass even further.

If he was not going to be reelected, and slavery was going to continue, Lincoln was starting to worry that not enough black people were getting to Union lines before this precious window of freedom closed.  The President said, “I want you to set about devising some means of making them acquainted” with the Emancipation Proclamation, and then to have some way of  “bringing them into our line.”  In words that Douglass underlined in a letter to a friend, Lincoln then added, “Now was their time—and that such only of them as succeeded in getting within our lines would be free after the war is over."

Douglass understood the radical nature of this proposal better than anyone. Almost exactly five years before, John Brown had been executed for encouraging slaves to rise up and claim their freedom. At the time, Lincoln the long-shot presidential hopeful had denounced Brown’s zealous actions.  Now a weary president was asking Douglass to formulate a plan that facilitated this kind of uprising.  If it were no longer possible for Lincoln to win, with time running out, the formally cautious Lincoln wanted as many people as possible to save themselves before his presidency went down.

After the meeting, Douglass drafted a plan involving a secret tide of agents, "conductors," operating behind enemy lines to communicate with the enslaved and usher them north. In the end, with the fall of Atlanta making his reelection more likely, Lincoln did not feel the pressure to enact Douglass’ plan.  But in the darkest days of his presidency, that Lincoln proposed such a radical idea illuminates how a president can decide to use what power and time they have left to do what they believe is necessary.

Though Obama’s future proposals on immigration are obviously different from the agony of Lincoln’s emancipation quandary, activists with the radical spirit of Frederick Douglass are pushing the president to take stronger executive actions. 

150 years on from Lincoln and Douglass, others take their turn in these same roles as president and agitator.  Whether this generation of activists will ultimately end up as satisfied as Douglass was at the audacity of their president’s readiness to act will be seen in the weeks ahead. 

Kendrick is the co-author of Douglass and Lincoln: How a Revolutionary Black Leader and a Reluctant Liberator Struggled to End Slavery and Save the Union (Walker Books). He can be followed on Twitter @PaulKendrick84.