His life changed when his father died suddenly, when Consider was only 11. Tryphosa remarried, but the stepfather did not look kindly upon young Consider. After a serious "misunderstanding" two years later, Consider was driven from home. He worked a variety of jobs to support himself, working for farmers, in a sawmill, as a house painter, in a country store, and in a post office.
Despite his hardships, Consider never lost his interest in education. His intuition had become evident early in his life, through the nature studies he had conducted on his father's farm, and he was also an avid reader. Despite his difficulties with his stepfather, Consider's mother continued to help pay for his education. He acquired a secondary education at the Onondaga and Cortlandville academies, and then attended the New York State Normal School for the 1860-61 and 1861-1862 terms. He graduated from the Normal School on July 10, 1862.
On August 14, only a month after graduation, he responded to a circular from Normal School math professors Rodney Kimball and Albert Husted, and joined the newly formed Normal School Company. After the company was officially mustered into the 44th NY on September 25, 1862, Consider was elected First Sergeant, the highest ranking non-commissioned officer in the company.
Consider's first battle was Fredericksburg, and he was with the regiment as it moved toward the stone wall and the Sunken Road on Marye's Heights in the dark on December 13. After the regiment was relieved from its position the following evening, it returned to the town to rest. As Consider sat on a sidewalk, among the many wounded soldiers, he wrote a letter to Professor Jewell at the Normal School concerning the progress of the battle. His letter was published in the December 20 issue of the Albany Evening Journal.
He survived the battle unscathed, and celebrated Christmas with the regiment. He caught a cold during Burnside's infamous "mud march" and it developed into bilbious fever. He was away from duty from January 25 to March 1, 1863. During this time, on January 28, First Lieutenant William Kidd left the 44th to become lieutenant colonel in a new cavalry regiment. As first sergeant, Consider, a staunch Republican supporter, was next in line to be commissioned a lieutenant. Politics cost him, however. He was passed over for Commissary Sergeant Rudolphus Warner, a Democrat, who was ill with yellow fever and absent from the regiment. Willett was highly respected by his fellow soldiers, including Private James Woodworth, who viewed Consider as one of the bravest and hardest working men in he regiment, and believed he was being treated unfairly by the officers because of his political beliefs.
Consider's performance at Gettysburg on July 2 brought his abilities into the open, so that no officer could deny his worth. In between the Rebel charges against Little Round Top, Consider led four men in front of the Union lines to round up 96 Confederates, who were pinned down and trapped behind the large rocks in front of the 44th NY's position. The prisoners included a captain, and Willett's prizes included two swords and a colt revolver. Albert Husted believed that Willett had earned a commission at Gettysburg, and that "it was through him principally that Company E took the ninety prisoners."
Stonewalled in an attempt to gain a commission in the 44th, Consider took leave from the regiment in early September, and went to Washington for examination as an officer with the newly formed Colored Troops. He was one of the first men to take the test, and passed as a captain. The army assigned him to the 2nd United States Colored Infantry as captain in command of Company G, and he left the Normal School Company for the last time on October 5, 1863.
Consider joined the 2nd USCT at its organizing camp in Arlington, Virginia. In December, the regiment was assigned to the Department of the Gulf, and sent to New Orleans. It was moved to Ship Island, Mississippi, and was then transferred to the District of Florida on February 13, 1864, where the regiment spent the remainder of the war.
The 2nd USCT was initially assigned to Key West, from where on April 1 and 7, Consider wrote letters to his cousin, Gordon Willett, and Gordon's wife Mary. Fort Taylor in Key West served as headquarters for operations on the western coast of Florida. On April 18, 1864, Consider's company was detached from the regiment and stationed at Fort Myers. At Fort Myers, Consider was placed in command of the 2nd Florida Cavalry (a white Union unit). He supervised the capture of 300 head of cattle, and on the return from this feat, a cart trail was discovered, leading to the capture of two blockade runners that were full of cargo.
During May and June, the tropical climate of Florida began to bother him. In May he was treated for dysentery, and in June, Firbris Remittent. During the latter half of 1864 and early 1865, the 2nd USCT participated in mainly in garrison duty and small raids on the Florida coast. It was not until March of 1865, that the 2nd USCT saw its first battle, near St. Marks, Florida. After the fall of the last major Confederate port, Wilmington, North Carolina, rumors spread in Key West that blockade runners were bringing increased amounts of supplies into St. Marks, a natural port located on the Florida panhandle near Tallahassee, the state capital.
Brigadier General John Newton led about 900 men, including 6 companies of the 2nd USCT, and landed at St. Marks Lighthouse, only 18 miles from Tallahassee, to capture, first the port of St. Marks, and then the capital. From the lighthouse, the attacking force needed to cross two rivers, the East River and the St. Marks River before reaching St. Marks. Early on March 5, Captain Consider Willett led two companies of skirmishers against the East River Bridge. The Confederates had torn up the bridge planks, but still defended the opposite bank. Willett captured a 12-pound bronze Napoleon cannon abandoned by the enemy, which retreated at the sight of advancing force.
Newton still believed he had the element of surprise, but in Tallahassee, the alarm had sounded almost as soon as the Union force had disembarked. Newton hoped to cross the St. Marks River by bridge in the small town of Newport, several miles above his intended target of St. Marks, but the Confederates had set fire to the bridge by the time the Union soldiers had arrived. A charge by the 2nd Florida Cavalry to save the bridge was repulsed, and Newton was forced to choose a new location. He learned of a place several miles further upstream where the river disappeared underground, and chose to cross at this new location, Natural Bridge, and make it there with a late-night march. The enemy learned of this movement, and when the Union advance arrived at Natural Bridge, it found the crossing blocked by the Rebels.
Newton ordered a daylight attack, led by Consider Willett's Company G (Willett's company) and Company B of the 2nd USCT. They successfully drove the pickets across the bridge, but had their progress halted by the main enemy line on the other side of the bridge. The men quickly dug trenches under fire, and faced a stalemate. Newton considered alternate crossings nearby, but found them either impassable or heavily guarded. The next morning, March 7, he decided on a two-pronged attack that included a flank attack and a frontal assault. Major Benjamin Lincoln of the 2nd USCT was to lead the frontal assault of 3 companies, including Company G. The flank attack, after an initial success, "encountered a wide and deep slough impassable to troops," leaving the 3 companies of the frontal assault to face the entire Rebel force. Lincoln's column, as it passed through a narrow defile of about 40 yards in length, received the attention of all 6 Confederate cannon, and most of the infantry. The attack failed, and the major was mortally wounded.
Newton retreated a short distance and devised a defensive position. The Confederates viewed the retreat as a sign of weakness, and charged across the bridge, expecting to rout a retreating foe. The Federals were waiting for them, and quickly dispatched the counterattack. With Newton's expected naval support having deserted him, he ended the expedition, and returned to Key West. Three officers of the 2nd USCT were killed during the battle, and most of the rest were wounded, including the commander of the regiment, Colonel Townsend. Consider was one of the few spared from injury. Out of the 900 men, 21 were killed, 89 were wounded, and 38 were missing. The 2nd USCT had proved itself in battle, but at a heavy price.
The price had been so severe that Captain Willett was placed in command of the 2nd Battalion from March 12 to April 8, 1865. By June 5, he had contracted yellow fever, and was in the hospital at Fort Taylor on Key West. He was examined by the regimental surgeon, William McCully, who determined that he had a disability, and recommended a change of climate. Consider was sent north to Kalamazoo, Michigan to recuperate. A Dr. Finch examined him, and confirmed the disability. Consider resigned his commission, and was discharged from the army on September 12, 1865. He returned to New York State, and applied for and began receiving a pension on October 23, 1865 in Canandaigua, NY. He attended medical lectures for a term at Bellevue Medical Hospital College in New York City. That failed to hold his interest, and he next entered the Albany Law School. He was admitted to the bar in Albany in April, 1866, and practiced law in Syracuse for a brief time. The brief time he spent in Michigan must have made an impression on him. When he decided to continue his law studies, he chose the Michigan University Law School, from which he graduated in 1867.
On November 5, 1867, Consider married Lois Ada "Addie" Wilder, in Ann Arbor, Michigan. He did not remain in Michigan for much longer, and settled in Chicago with his wife by 1868, where he soon opened his own law office. He was victimized by the "Great Chicago Fire" of October 8, 1871, which left his law office and papers "a smouldering ruin." Within three days he was working out of a doctor's office. Right after the fire, he was scheduled to argue a case to the Illinois Supreme Court. An important legal brief had been burned in the fire, and when he arrived he was broke and had to sleep in a chair. He was the first lawyer from Chicago to appear before the Court after the fire, won his case, and established a reputation as a tireless and persistent litigator.
By 1875, Consider had become interested in public service, and in April of that year was appointed Village Attorney of Hyde Park, Cook County, Illinois. He was reappointed in 1876 and 1877, and was the first to publish the ordinances of Hyde Park – all 400 pages of them. His growing reputation led him to an appointment as County Attorney for Cook County in 1879. He was reappointed at least twice – in 1880 and 1881. He refused to let politics influence any of his decisions.
One of Consider's most famous cases in Chicago centered around the testing of a new statute consolidating the towns of South, West, and North Chicago into the town of Chicago. If the consolidation was not voided until after the election, then millions of dollars of taxes would have been lost, as the elected officers of the new town would only have authority in one of the three old towns. Willett was able to find a solution that had eluded the other attorneys. He had a citizen of West Chicago appear before a justice of the peace in South Chicago in order to have the judge acknowledge a mortgage. The judge refused, claiming that the towns were not properly consolidated, and that only a judge in West Chicago could recognize the mortgage. Consider brought the case before the Illinois Supreme Court, asking them to force the South Chicago judge to acknowledge the mortgage. They refused, and before the election, announced that the towns were not consolidated.
In his private practice, Consider originally practiced both civil and criminal law. By the time he had become County Attorney, he had decided to limit his focus to civil practice, as an expert in constitutional, corporate, equity, and real estate law. The one legal arena in which he lacked success was his battle with the pension office in Washington, D.C. The federal government stopped his pension in 1875 after a medical exam declared him fit. On June 11, 1887, while living at 69 University Place in Chicago, Willett applied for the reinstatement of his pension. On November 7 of that year, he filed with the Cook County clerk that he was unable to perform manual labor, but the pension office refused his claim. Consider applied again in 1902, but his success is unknown. He died on October 12, 1912, in Chicago, at the age of 71. His wife applied for a widow's pension on February 18, 1913, which she continued to receive up until her death on July 12, 1936, at the age of 87.
Consider Willett stood "in the front rank of his profession, being a skillful and fearless leader," and was involved in several political, social, and fraternal organizations. He was "frank and outspoken to bluntness," and was an "exposer of fraud and duplicity in every form." The people of Chicago considered him "modest, firm, simple and self-poised," and believed that "his fame shall be earned not alone by things written and said, but by the arduous greatness of things done." The same ability he displayed in his youth and during his service with the Normal School Company, helped him become a successful lawyer and community member, and endeared him to the people of Chicago.