In October of 1886, after consolidating his two ranches under Ferris and Merryfield, Roosevelt was again back home in New York. The political arena was somewhat different this time around, as the radical Henry George had been nominated to head up the new Labor party in the mayoral election of New York. At first neither of the two major parties paid much attention to George's campaign, but only ten days after his nomination it was clear that the labor party was a serious contender in the election.

Roosevelt for his part had intended to attend the Republican County Convention as an observer, but was approached by a group of men to head up the Republican ticket for mayor. Roosevelt, as a true party man, could not refuse the nomination even though no one in the party gave any Republican much of a chance at winning a three-way contest. Roosevelt, as always, threw himself wholeheartedly into the race.

The race would prove to be a close one, with George running on a platform to the far left, the Democratic candidate Hewitt running in the center, and Roosevelt on his conservative far right platform. Roosevelt once again was not a man to mince words. In the campaign Roosevelt gained a great deal of momentum with his speeches from the stump. In fact one poll by the U.S. Chief Supervisor of Elections projected a total vote of 85,850 for TR, 75,000 for Hewitt, and 60,000 for George. Roosevelt would keep up a blistering pace of speeches. On October 29 alone, between the hours of 8:00 P.M. and 11:00 P.M. he would deliver five different speeches at five separate locations across the city. Despite his colossal effort, and partly due to the fact that the party regulars fearing a George victory had bailed out in favor of Hewitt, Roosevelt would come up short at the polls on Election Day. The final count on November 2 would show 90,552 for Hewitt, 68,110 for George, and 60,435 for Roosevelt. The election would be considered one of the cleanest elections in the history of the city, with an unprecedented voter turnout.

Only four days after the election, Roosevelt was on board the ship Etruria with his sister Bamie headed for England. He had been secretly engaged to his childhood sweetheart, Edith Carow and would be married in England on December 2, 1886. While on the honeymoon in Europe, news would begin filtering in about the bad winter blizzards in the Dakota Territory. Roosevelt knew the dangers of a harsh winter on his cattle endeavor on the Little Missouri, but would have to wait until his return to the States to find out how bad the damages were. In the mean time as the trip in Europe progressed Edith would begin to suffer from morning sickness of the honeymoon baby she was carrying.

On March 28, 1887 the couple would return and move into the house on Oyster Bay which was now renamed Sagamore Hill. Roosevelt had received word from Merrifield and Ferris on the Little Missouri to hurry west and see for himself the damage of the horrid winter. It would take him until April 4th to finally head west, as he would first need to clear up the issue of who would now take care of Baby Alice. Since the birth of Alice his sister Bamie had been charged with the care of his little girl. Now Edith would not hear of his sister raising the child, and so arrangements needed to be made to bring Alice to live with the Roosevelts at Sagamore Hill.

When TR finally reached the Little Missouri the situation was even worse than he had imagined. The drought of the summer left the cattle weak and with the piles of snow in the winter, entire herds were wiped out. As he traveled through the Bad Lands Roosevelt would see piles of blackened carcasses everywhere. It was estimated that on the average the cattleman of the Bad Lands lost between 75 to 85 percent of their cattle during the winter of 1886-1887.

During the summer of 1887 Roosevelt returned to his historical writing. Houghton Mifflin publishing company offered him a second opportunity at a historical biography in the American Statesman series. His first effort on Thomas Hart Benton had been received well enough for them to offer Roosevelt a second subject, Gouverneur Morris. Roosevelt did a respectable job on this work despite the fact that the Morris family would not let TR see any of the old gentleman's papers.

By late October of 1887, Roosevelt headed west once again to hunt big game. This time, however, Roosevelt was shocked to find out how depleted the big game had become in the West. This would strike a chord with him and open his eyes to the need for conservation of the big game before it reached extinction. On December 8, 1887 Roosevelt would entertain a group of wealthy men as dinner guests to discuss his ideas on conservation. One of the guests on hand was George Bird Grinnell, who was the editor of Forest and Stream. In January of 1888, what started at that meeting in December would formally organize into the Boone & Crockett Club with Theodore Roosevelt as its first president. Roosevelt would remain the head of Boone & Crockett until 1894. During that time many influential men in the country joined the organization and gave it a substantial amount of power in Congress. The Boone & Crockett club played a part in the creation of the National Zoo in Washington. It also helped push through the Park Protection Act of 1894 which played a large role in saving Yellowstone from over commercialization. One of the boldest strokes to aid in conservation, helped through by the Boone & Crockett organization, was the Forest Reserve Act. This legislation gave the President of the United States the authority to set aside any wooded or partly wooded country in order to protect the quickly depleting standing timber of the west. This very legislation would be used time and time again by Theodore Roosevelt as President.

The year of 1888 would bring the writer in Roosevelt into full bloom. He had long wanted to be known for his writing, but more importantly as a serious historian. In January of 1888 he began laying out plans for a multi-volume work on America's conquering of the West which he would entitle Winning of the West. He managed to get a contract with Putnam's to deliver the first two volumes of the work by the spring of 1889. By December of 1888 he had completed volume one, laying down his pen at the completion of volume two in April of 1889. These two works alone in 1888 would have kept most men busy, but the staggering costs of maintaining Sagamore Hill forced Roosevelt to supplement his income with other writings. During the year of 1888 he would publish in the North American his "Remarks on Copyright and Balloting", with Century publishing his six essays on ranch life in the West. These articles would later in the year be revised by Roosevelt and published in book form in Ranch Life and the Hunting Trail. In May of that year Gouverneur Morris was published, in September Murray's Magazine would publish his "A Reply to Some Recent Criticism of America". October would bring Essays in Practical Politics which was a remake of two previously published works which were revised in book format.

With all of this writing in 1888 you would think that the politician in Roosevelt had somehow gone dormant. The presidential campaign of 1888 presented the tariff as a major issue. Despite misgivings by the party regulars, Cleveland came out in favor of doing away with the high protective tariffs which protected American businesses. This gave the Republicans an inroad, and they chose as their candidate, Benjamin Harrison, grandson of William Henry Harrison, a Civil War political general, and ex-senator. Harrsion was known as a gifted orator, and Roosevelt believed him to be a good candidate. The problem with Harrison was that he could stir people with his words, but upon meeting them personally could turn them to ice. The goal of the Republican party therefore was to get exposure for Harrison without having Harrison make personal contact. For that purpose, the Republican party would look to the young and fiery men like Roosevelt to take to the stump on his behalf. For his part Roosevelt would take to the stump in October for a twelve-day tour in Michigan and Minnesota. When Harrison was elected Roosevelt hoped for a political appointment to get him back into politics, and also to give him a stable income to pay some of the costs of maintaining Sagamore Hill.

Roosevelt would not approach Harrison directly, but instead went through his friend in Congress, Henry Cabot Lodge. An effort was made to get Roosevelt the Assistant Secretary of State position. Harrison had promised the Secretary of State position to James G. Blaine who, once nominated had been supported by Roosevelt in his bid for the presidency of 1884, but had been vehemently opposed by Roosevelt to get the nomination. Thus, Roosevelt was passed over for the Assistant Secretary of State. Roosevelt, however, was rewarded for his service in the campaign with one of the three Civil Service Commissioner jobs. The Civil Service Commission was started in order to take away the spoils system of rewarding political hacks for their work with government plums and replacing it with a system of promotion on merit. Ironically, Roosevelt would get a civil service commission job as a reward for his political service, although Roosevelt would never see it that way. Roosevelt, the reformer, was perfectly molded for the position, although it was a thankless job on a small annual salary of $3,500. Harrison was elected, losing the popular vote, but winning the electoral vote. The spoilsmen were everywhere now seeking some plum to repay them for their efforts. Roosevelt, with his high sense of honor and disdain for the spoils system, would be kept busy over the next six years. As a Civil Service Commissioner, a man was in a no-win situation. If he did his job well, he would lose favor with his own party who, seeking to repay favors, did not want to see the spoils system dismantled. Yet if he failed to do his job well, he would bare the full brunt of the criticism of the reformers. Most Civil Service commissioners were content to pass their time going to the social parties in Washington and giving the appearance of accomplishing something. This notion was foreign to Roosevelt, and he characteristically jumped in with both feet marching in on his first day of being sworn in and taking the largest office available. Although the other two men on the Civil Service Commission were his seniors, Roosevelt immediately took the leadership role.

As Commissioner, Roosevelt bumped heads with Postmaster General John Wanamaker, a spoilsman through and through. Roosevelt was investigating many abuses throughout the Post Office and many of them pointed back to Wanamaker. As a Civil Service Commissioner Roosevelt quickly made enemies of some of the party regulars, which in the long run he feared would not help his political aspirations. Though Roosevelt didn't make a lot of political friends his endeavors as a Civil Service Commissioner threw him into the national spotlight.

The election of 1892 was a repeat of the 1888 campaign pitting Cleveland against Harrison. This time around, Cleveland would prevail and it seemed to Roosevelt that his time in Washington was short. However, at least one of the three Civil Service Commissioners, by law, had to be from the minority party and since Roosevelt made so many Republican enemies in office, it made sense for Cleveland to keep him on board since he was in essence the best 'worst' Republican. Since the Civil Service Commission was about doing away with the spoils system, by retaining Roosevelt, Cleveland would appear to be not playing the spoils game. Thus, Roosevelt would remain on the Commission for part of Cleveland's term.

As the political winds were blowing it was obvious to Roosevelt that the Republicans were going to win across the board in 1896. He thought remaining on the Commission through part of a Democratic term would look as if he were trying to do what was good for the country. Nevertheless, he also wanted to distance himself from the ship which he could see sinking and didn't want to appear to be a party sell out. Thus, in 1894 when Republicans again asked him to run for the Mayor of New York he truly wanted to jump at the chance. Edith was not as certain and didn't want Teddy giving up a paying job for the insecurity of elective office. Roosevelt would later regret following her advice, but he nonetheless turned down the nomination. When Mayor Strong took over the office in New York he offered Roosevelt the job of Commissioner of Street Cleaning. Roosevelt found this job less than appetizing and turned it down, all the while hoping for a more lucrative offer. The offer would come in the form of a member of the Board of Police Commissioners.

On May 8, 1895 Roosevelt reported to the Police Headquarters, called a meeting of the new board and promptly had himself elected president. The others serving with him would be Major Avery D. Andrews, Frederick D. Grant (son of Ulysses S. Grant), and Andrew D. Parker. The commission was mandated to be composed of two Democrats and two Republicans to insure bipartisanship, with the president having no more authority than any other member and each having veto power. This actually left the commission quite handicapped to accomplish anything. The commission was handicapped further by the fact that the mayor appointed the commissioners but could not remove them without the consent of the governor. Beyond that the commission appointed the police chief, but he could not be removed without a hearing and judicial review. The patrolmen on the beat were also appointed by the commission but could not be easily removed. Roosevelt quickly overshadowed the others in the headlines and in action and in so doing stirred up jealousy among the other members.

For Roosevelt, the Police Commissioner job had advantages other than purely political ones over that of the Civil Service Commission. It paid $6,000 a year and was much closer to Sagamore Hill than the distant Washington. This would give Teddy more time with his ever-growing family, which now consisted of Alice, from his first marriage, Ted born in September of 1887, Kermit born in 1889, Ethel in 1891, and Archibald in 1894. Only Quentin would follow in 1897 to round out the family.

The New York City police department was corrupt through and through when Roosevelt took over his post. Roosevelt would find as an ally in his war against this rot, Jacob Riis, the author of How the Other Half Lives, a book on the poor living conditions in New York's slums. Riis was familiar with the city and its corrupt police force and how it operated. Bribery was not only rampant, but accepted behavior, with the payments being divvied out from patrolman up through the ranks. This was made all that much more apparent when the Rev. Charles Parkhurst, from the Presbyterian Church on Madison Avenue began a crusade against the corruption of the police force.

Roosevelt, along with Riis, would of often be found undercover on the streets of New York in the middle of the night, looking for officers who were derelict in their duty. On one of his first outings he did not have to look far. Wearing clothes that made them look exactly like the suspicious characters that the patrolman should have been looking for, Riis and Roosevelt headed east on Forty-second Street. They came across a waiter who was carrying a tray full of food and grumbling to himself, "Where in the blazes does that copper sleep?" This comment obviously made in reference to the patrolman to whom he was supposed to be delivering the food, who often slept on his beat. In a short distance they came across another patrolman who was fast asleep on a buttertub and snoring so loudly that he may have kept the rest of the neighborhood awake. A third patrolman was seen actively involved with a prostitute. The first patrolman that Roosevelt came across who didn't appear as being derelict in his duty was actually on the wrong beat. When questioned by Roosevelt the officer, not knowing who his interrogator was, lied and was flip about it. The next day Roosevelt had all of the violators before him at headquarters for a raking over. With Roosevelt in charge, this behavior would no longer be acceptable.

The problems weren't just with the patrolmen, but spread all the way to the top. Roosevelt would also set his aim on the police chief Thomas Byrnes. In fact, investigators discovered that Byrnes, a man who had worked his way through the ranks had amassed a fortune worth more than $1,500,000. When questioned as to where the money had come from the police chief simply said he had accumulated the money from investments made on tips from Jay Gould.

Also in Roosevelt's sights was Inspector Alexander Williams, known as "Clubber" Williams, for his extraordinary use of the baton in keeping order. It was Williams who is credited with the age-old axiom that "There is more law at the end of a policeman's night stick than in any ruling of the U.S. Supreme Court." Williams was viewed so highly in the force as to almost be immortal. Williams himself had his own ideas of how to cure the problem in the police department. He favored legalizing houses of disrepute in certain areas. The women who worked them could therefore work without any harassment from the police as long as they operated within the boundaries set up for such purposes. He also came out against enforcement of the Excise Law, which forbade the selling of liquor on Sundays.

This law forbidding the sale of liquor on Sundays was one of the biggest problems facing Roosevelt. He himself was not an advocate of prohibition, but the law was put on the books to appease the prohibitionists. Prior to his arrival on the police commission the law was only sporadically enforced and then only when the proprietor was late with his payment for protection. Roosevelt was encouraged to ignore the law, but this went against all he believed and as long as the law was on the books, he would enforce it. The problem as he saw it was that having the patrolman look the other way for that crime opened up a whole host of other offenses that they would overlook. Thus the door for corruption would be left wide open.

His battle against the corrupt men of the upper echelons of the force went in Roosevelt's favor. Although they were not fired or prosecuted, four of them including Byrnes and Williams retired early. The fight against the Sunday liquor sales was far more difficult to win. Tammany Hall attacked Roosevelt for trying to keep the 'working Joe' from having a little drink and relaxation on his day off. Not only did the Democratic machine rally against his fight, but they were soon joined by the Republican machine headed by Senator Platt. Platt would encourage Roosevelt to drop the fight against the Sunday liquor sales, but when Roosevelt refused Platt would take a different route. Platt controlled the government at Albany and privately told Roosevelt in January of 1896 that by means of legislation, the police commission would be done away with. Roosevelt had done a great deal to cleanup the police department and had brought about numerous changes to improve morale and the day-to-day operations. Included in some of his innovations was the addition of officers on bicycles, making use of the new technology. He would also bring about the standardization of the firearms used throughout the department. But toward the end of his time as commisioner he would write the following to his sister Bamie as evidence of his frustrations, "I have to contend with the hostility of Tammany, and the almost equal hostility of the Republican machine. I have to contend with the folly of the reformers and the indifference of decent citizens; above all I have to contend with the singularly foolish law under which we administer the Department ... Add to this a hostile legislature, a bitterly antagonistic press, an unscrupulous scoundrel as comptroller, quite shameless if he can only hamper us." For his part he had accomplished all he could accomplish under the conditions in which he was forced to operate.

Fortunately for Roosevelt the presidential election of 1896 would need his services on the stump. McKinley was going up against the man nominated by both the Populist Party and the Democrats, William Jennings Bryan. Bryan stood for 'free silver', which Roosevelt and the Republicans strongly opposed. Roosevelt also came out against the double nomination because each party had also nominated a separate Vice President. Roosevelt's attacks were fast and furious, and he hoped that his actions would bring him some appointment in the new administration, preferably an assistant secretary position. McKinley won by a landslide and Roosevelt was rewarded with the position of Assistant Secretary of the Navy. Even this position was a struggle for Roosevelt to gain in that McKinley wanted approval from Senator Platt, the Republican machine head from New York, before appointing someone from his state. Platt did not become the head of the machine without political savvy, and realized the Roosevelt could bother him less in Washington than as president of the police commission. Thus, Roosevelt would leave the police commission in New York and move to Washington.