After his brief honeymoon at Oyster Bay, Roosevelt enrolled at Columbia Law School. Roosevelt studied hard at Columbia, and in his spare time did research for his first book on the naval history of the War of 1812. Even with his studies in full swing, Roosevelt looked forward to May when he and Alice would take a fitting honeymoon to Europe.

On the trip to England, Alice proved to be a worse sea traveler then Teddy himself, and it took her some time to recover from her seasickness. The pair would make their way to Switzerland where Roosevelt would be tested both physically and emotionally. It was here with his father, that he climbed the mountains, and first began his climb out of his childhood illnesses. On this trip to Europe, he would continue to test himself physically attempting to climb some of the most challenging peaks. Teddy would hire two guides and successfully climb the Junfrau. From there it was on to the Matterhorn which up until sixteen years earlier had never been climbed. Many men had lost their lives on these slopes, and it would be the most difficult challenge yet for T.R. Roosevelt commented on the Matterhorn, "I was anxious to go up it because it is reputed very difficult and a man who has been up it can fairly claim to have taken his degree as, at any rate, a subordinate kind of mountaineer." The first of the two-day climb would be nine hours long. The night was spent in a hut, which was dug into the side of the rock, the floor being ice. The second day began at 4:00 AM to enable them to reach the summit and get back down before the sun could melt any of the ice, making the climb even more treacherous. Once again Roosevelt lived up to his own challenge and successfully completed the climb.

On returning to New York, Roosevelt would again rub shoulders in social events with the best in New York, yet his life would also begin a walk down a different road. One night a month Roosevelt could be found with the more shady characters of New York in the political arenas of Morton Hall, the headquarters of the Twenty-first District Republican Association. When the news of these activities leaked out to his father's friends in the upper echelons of business they at once looked down on them, for the wealthy looked down on the dealings of the machine hacks and politicians. Roosevelt responded, "... that if this were so it merely meant that the people I knew did not belong to the governing class, and that the other people did - and that I intended to be one of the governing class; and if they proved too hard-bit for me I supposed I would have to quit, but that I certainly would not quit until I had made the effort and found out whether I really was too weak to hold my own in the rough and tumble." ¹

Roosevelt went to the meetings at Morton Hall to get to know the men there, and also to have them get to know him. The leader of the local machine was Jake Hess who remained rather distant from Roosevelt. Hess had under him many captains, one of which was an Irishman by the name of Joe Murray.

Murray was a man who, when not even 18, had registered in the Union army and fought valiantly. Upon returning to New York he was brought into the Tammany Hall machine where his task was to take his gang of thugs, and to rough up the Republican election leader and to send him and his ballots flying. At this task he was very adept until his leader got a big head, and forgot where his support had come from. Joe Murray was not a man to forget, and at the next election had his men reverse the trend and attack the Democrats of Tammany Hall. The result was that the Republicans won in a district in which they had previously never managed to get more than about 10 percent of the vote. Joe Murray was quickly brought into the Republican ranks and rewarded for his undertakings.

As Roosevelt frequented Morton Hall he would strike up a friendship with Joe Murray who, at that time, was looking to unseat Jake Hess. Murray had kept a careful eye on the young Roosevelt and had been favorably impressed. Murray threw his substantial support behind Roosevelt and won him the nomination over Jake Hess. Jake Hess for his part took it all in stride and then worked with Murray to get Roosevelt elected. At first the two thought they would take Roosevelt out to canvas the saloons on Sixth Avenue. Roosevelt was introduced to the first saloonkeeper who immediately began to interrogate him. At that time the saloonkeepers held a substantial amount of weight among the voters and it would be of utmost importance to favorably impress them. The saloonkeeper pulled no punches and told Roosevelt that he was expected to treat the saloonkeepers fairly. Roosevelt, not liking the tone in the man's voice, indicated that he hoped to treat all business interests fairly. Not satisfied with Roosevelt's response, the saloonkeeper informed Roosevelt that he thought that the liquor license was too high. T.R. responded that he thought it was too low, and he hoped to raise it. At that point before things could get any more heated, Murray and Hess stepped in and escorted Roosevelt outside. They informed him that he should go back to Fifth Avenue and that they would take care of things on Sixth Avenue. The two men fulfilled their promise, and Roosevelt was elected to his first political office in the fall of 1881. There was an understanding that when elected Roosevelt would not be bound by the machine, but would stand for what he felt was best for himself and his fellow man. This would prove to be the Roosevelt policy for his entire political career.

Along with his political success in the fall of 1881, in December, Roosevelt would send the manuscript for his book on the naval history of the War of 1812 to the publisher. The book would be well received on both sides of the Ocean and was considered to be one of the best books ever written on the subject. The book would go to a third edition, and be used as a textbook at several colleges. As evidence to the quality of the book, a law would be enacted requiring at least one copy of the book on every Navy ship.

When Roosevelt stepped foot into the Assembly for the first time on January 3, 1882 he was the youngest man on the floor, at age 23. He was a Republican from the wealthiest district in a legislature controlled by the Democrats. The full legislature had 128 members, which contained 61 Republicans, as well as 8 Tammany men among the 67 Democrats. The legislative life did not prove to be all that the new young assemblyman had hoped for. The first action to be performed was to select a Speaker. The Tammany men, who split from the 59 regular Democrats, knew that they had the swing vote to be used by either party to get the necessary 64 votes to elect the Speaker. They hoped to deadlock the legislative process to force one of the two major parties to compromise and give Tammany Hall men some choice committee jobs in return for their votes. For days the deadlock went on with each Assemblyman showing up for roll call only to go home again with nothing else to do. On January 24, 1882, when a fellow Republican stood up and suggested that the minority party compromise with the majority to beat the Tammany impasse Roosevelt leaped to his feet and gave his first speech on the floor.

His speech was a success, and his party took his advice. When, in February, the Tammany men finally gave in a Democratic Speaker was elected. Roosevelt was appointed as a minority member of the coveted Committee of Cities.

During the impasse, two incidents of note occurred. One of the Tammany Hall men, John MacManus, disliked the 'dude' Roosevelt and reportedly had said that he would toss "that damned dude" in a blanket. Roosevelt felt no love for the Democrats and especially not for the Tammany Men as can be seen through some of his writings early in the session. "There are some twenty-five Irish Democrats in the House. They are a stupid, sodden, vicious lot, most of them being equally deficient in brains and virtue." Of the Tammany Hall men he wrote, "totally unable to speak with even an approximation to good grammar; not even one of them can string three intelligible sentences together to save his neck." Roosevelt was even more critical of MacManus himself saying, "a gentleman named MacManus, a huge, fleshy, unutterably coarse and low brute, who was formerly a prize fighter, at present keeps a low drinking and dancing saloon, and is more than suspected of having begun his life as a pickpocket."² When Roosevelt caught wind of what MacManus had proposed he charged up to him and fumed, "By God! MacManus, I hear you are going to toss me in a blanket. By God! if you try anything like that, I'll kick you, I'll bite you, I'll kick you in the balls, I'll do anything to you - you'd better leave me alone." MacManus backed down and his threat was never carried out.

The second incident happened while Roosevelt was out with several friends, who were also Republican Assemblyman. The grouped stopped at a saloon for some refreshment when a Tammany man, J.J. Costello, saw Roosevelt decked out in the fashionable short pea jacket. Costello yelled out some insult to Roosevelt about his jacket and Roosevelt, in a fit of rage knocked him down. When he got up Roosevelt hit him again and again Costello went down. When he got up the second time, Roosevelt hit him again. Then Roosevelt said to him, "Now you go over there and wash yourself. When you are in the presence of gentlemen, conduct yourself like a gentleman." Roosevelt then proceeded to buy Costello a beer and forced him to drink it. "I'm not going to have any Irishman or anybody else insult me," Roosevelt said later, still bristling. ³ These incidents only highlight Roosevelt's typical lightning response to adversity, and his iron will not to back down.

Within 48 hours of joining in Committee work, Roosevelt had introduced four bills. These bills were all reform bills, and even though only one of the bills was passed, Roosevelt began to build his reputation as a young reformer. It didn't take Roosevelt long to realize that about one third of the legislature was corrupt. Roosevelt was indignant at the corruption both in the House and with the pillars of Capitalism, like Jay Gould. It was here that Roosevelt struck and struck hard. He became aware of a corrupt State Supreme Court Justice, T.R. Westbrook, who through treachery enabled Gay Gould to purchase the Manhattan Elevated Railroad at only five percent of its previous value. Roosevelt did a great deal of research and dropped a bombshell on the assembly that he demanded the Judiciary Committee investigate the conduct of Attorney-General, Hamilton Ward, and Judge Westbrook. Roosevelt became David taking on the Goliaths. The debate and investigation would go on for quite sometime with Roosevelt gaining great popularity in the press. Finally, when the Judiciary Committee completed its investigation Roosevelt had counted straw votes and knew he had enough votes for impeachment. At the last minute, however, before the vote could be taken many of the members were bought at a price of $2500 each and Westbrook and Ward would get off the hook. With the close of the session it was widely accepted that that assembly had been one of the most corrupt since the days of Boss Tweed. Roosevelt, however, came away as a bright and shining star that could not be tarnished by the corrupt men he had served with. Roosevelt would be elected to two more terms at Albany and in only his second term, still the youngest man in the legislature, would be elected as minority leader.

Prior to starting his third term, Roosevelt made two large acquisitions. On August 20, 1883 expanded his holdings around his estate at Oyster Bay by purchasing an additional 95 acres with a price tag of $20,000. On his total of 155 acres on he planned to build his future residence Leeholm, named after his wife Alice Lee. On September 3, 1883 he would travel out to the Dakota Territory for a hunting expedition. While at Little Missouri he would decide to invest in cattle ranching. On September 18th he would write a check to two of his future ranch hands for $14,000 dollars to start his ranch at Little Missouri. Interestingly enough, Roosevelt's total income for 1883, including royalties from his book, his $1200 dollar salary as an Assemblyman, and his inheritance from his father, would add up to $13,920. He was obviously spending money faster than he was making it.

With the start of his third term in the assembly, Roosevelt would again seek to lead his party. This time around, however, the Republicans were in the majority. The stalwarts of the party were more than willing to let Roosevelt head the party when they were in the minority, but now they balked at letting the young man become the Speaker. Roosevelt would run a good race, but in the end he would not wind up with enough votes to make him Speaker. Although he lost the nomination for Speaker, he was still politically strong and was made chairman of the powerful Cities Committee.

With his powerful committee position and his promise to the electorate that he would break the power of the machine politicians in New York City, Roosevelt threw himself into his work putting in 14-hour days. After three days in his new position, Roosevelt would introduce three reform bills aimed at the political machines. The first, although it would build his reputation as a reformer, had little chance of passing as it was aimed at raising the fee for a liquor license. The second bill proposed to change the way the city did things financially by decreasing the amount of money the city could borrow from unorthodox sources. The third bill, which would become known as 'The Roosevelt Bill' would change the power structure of the city government by taking the power away from the non-elected Board of Aldermen and putting into the hands of the mayor, who was elected by the people. The Board of Aldermen, who were merely machine appointees, had confirmatory power over all of the mayor's appointees. This left the mayor with little or no power, and put the real power of the city in the hands of the political machines. If 'The Roosevelt Bill' passed the power would finally fall into the hands of the mayor and make the city government more accountable.

While the battle over the reform bills was going on, Roosevelt was simultaneously acting as chairman of an investigating committee looking into the corruption of New York City. The man of boundless energy was thus running constantly between Albany and New York to keep up with the legislation and the investigation. It was during this time that Alice was due to give birth to their first child. Roosevelt grew concerned when Alice became ill just prior to her due date. On February 11, 1884 he received a letter from Alice assuring him not to worry about her and that the doctor was not concerned over the illness. Alice was far more concerned for Mittie, Roosevelt's mother, who had come down with a fever which the doctor felt might be typhoid. A telegram arrived in Albany for T.R. informing him that his daughter had been born on February 12th at 8:30 PM. Roosevelt did not have long to celebrate however, because a second telegram arrived informing him that Alice had taken a turn for the worst. He rushed home by train and reached Fifty-seventh Street late on the evening of February 13th. His brother Elliot met him at the door and bemoaned, "There is a curse on this house." For not only was Alice fighting for her life, but also Mittie was burning up with typhoid fever and there was nothing the doctor could do for her. Roosevelt spent the next sixteen hours keeping vigil and going from bedside to bedside. At 3:00 AM on the morning of February 14th Mittie would breathe her last. With his mother gone, Roosevelt would climb the stairs and sit by Alice's side hoping beyond all hope that she would pull through. At two o'clock in afternoon of the same day Alice would succumb to Brights disease. His diary entry for that date was marked with a large black X followed by the words "The light has gone out of my life." The devastating loss of both wife and mother on the same day caused Roosevelt to conclude the epitaph for his wife, "For joy or for sorrow my life has now been lived out."

Roosevelt could not seem to bare the pain of losing his wife. He gave away her pictures, which he could no longer bare to look upon. He would never mention her name again except on a few rare occasions, and he all but walked away from baby Alice who was put under the care of his sister Bamie. For several years, Bamie was the nurturer of baby Alice with Theodore simply paying child support. In an effort to combat the pain Roosevelt would return to his work, expressing his thoughts in the following words to a friend, "I shall come back to my work at once; there is now nothing left for me except to try to so live as not to dishonor the memory of those I loved who have gone before me." Strangely enough, in his Autobiography Roosevelt never even mentions the existence of his first wife.

Roosevelt kept to his word and returned to his work in Albany on February 18th with a vengeance. The investigation, which had been launched against the corruption in New York City, had been met with all kinds of obstacles thrown at him by the political machines. The final obstacle would be the report presented to the committee only days before it was due, which fell far short of what the committee members had thought fair and appropriate. With only two days left before the report was due the committee put the full responsibility for the drafting of a new report on the shoulders of Theodore Roosevelt. Roosevelt locked himself away in his office and armed with his notes began writing. He worked through the night and into the next day. When the assembly came to order Roosevelt was in his seat along with his writings. He would break from his writing long enough to jump up and comment on some piece of legislation before sitting down and continuing with his writing. There would be no time for corrections and as he finished each page it was rushed off to the typesetter. With the writing completed, the committee at once approved it just under the deadline. Roosevelt would manage to get seven out of his nine corrective bills into law.

In 1884 Roosevelt would step onto the national stage as a delegate at large from New York in the Republican national convention. The Republican party had split during that year over the nomination between Chester A. Arthur, who had taken over upon Garfield's assassination, and James Blaine of Maine whose character was somewhat dubious. Roosevelt didn't care for either man, Blaine because of his character, and Arthur possibly for his role in Theodore Sr.'s demise and more likely for his ties with Roscoe Conkling. At the New York convention at Utica Roosevelt and a small number of reformers chose to back Senator George Edmunds of Vermont. Because neither the Blainesmen nor those in favor of Arthur were willing to give the other side the majority the convention wound up choosing delegates at large of which Roosevelt was chosen to lead the uncommitted slate. At the convention Roosevelt would jump into the spot light by seconding the nomination for Thomas Lynch as temporary chairman of the convention. He would also make a short speech, which in Roosevelt's words, "was listened to very attentively and was very well received by the delegates, as well as the outsiders." Although Blaine would ultimately win the nomination, Roosevelt now had a taste of national politics, and it was a taste he would come to crave again and again. With the national convention in Chicago over, Roosevelt would again head west.