My first attempt at a timeline. Don't expect it to be that great, but we'll see. Don't have Microsoft Word either, so I did the best I could.

Glory and Chaos: An American Story
Part 1: "Victory!": The American Empire
1900 had come to America. A new decade. Along with it, a new sense of power. From Puerto Rico to the Philippines, the United States had the stars and stripes firmly on it's colonial possessions. Cuba, Puerto Rico, Hawaii, Alaska, Guam, the Philippines, and Midway all were under the American flag. It had given most Americans a new wave of pride. Gone was the divided nation of 1862. America in the year 1900 was stronger than ever. Like the empires of Europe, America had finally conquered it's own colonial lands. An American Empire.
President William McKinley was elected President during hard times. The Panic of 1893 had risen unemployment to almost 15%. Elsewhere, rising tensions with Spain over Cuba caused a new wave of Manifest Destiny to reach the minds of Americans. Now in 1900, unemployment was down to almost 5% and America had soundly defeated Spain in it's conquest of Cuba, Puerto Rico, and the Philippines. Of course, not everything was all well when the Unted States entered 1900. Democrats and the rising number of Socialists opposed McKinley and America's new era as an empire. The ongoing Philippine-American War also served as a negative for McKinley. 1900 was an election year. The Democrats were likely to nominate either William Jennings Bryan or Admirel George Dewey. Both were popular with many Americans and many Republicans feared a McKinley defeat, despite his accomplishments.
McKinley was obviously the nominee for Republicans. The one question was who would be his Vice Presidential nominee after Vice President Garret Hobart died in 1899 due to illness. Many Republican leaders did not want a Progressive on the ticket. The party leaders had a clear strategy. The wanted to pick a safe, experienced, and pro-business Republican and use McKinley's accomplishments of a lower unemployment level and the victory against Spain as campaign issues. Despite a strong push from Progressives at the convention in Philadelphia, it came up short with no major Progressive leader[1] and the efforts of conservative Republicans to stop them. In the end, the Republicans nominated Senator Stephen Elkins of West Virginia for the Vice Presidency. He was a well known and safe choice for Republicans. Elkins served as the Secretary of War under Benjamin Harrison and stayed in the public spotlight as he was elected Senator in 1895. McKinley and Elkins served as a solid Republican ticket.
The Democratic nomination for the Presidency would prove to be more eventful. Going into 1900, the popular William Jennings Bryan was in a heated race with war hero, Admirel George Dewey. Tragedy struck when in May 1900, a staunch anti-silverite assassinated Bryan during a public speech. This left George Dewey as the favorite and the eventual nominee for the Democratic nomination. Former Vice President to Grover Cleveland, Adlai E. Stevenson, would fairly easily secure the Vice Presidential nomination. With much sympathy going to the Democrats after Bryan's assassination, the 1900 Presidential election looked to be a close one.
George Dewey, Democratic nominee

The Presidential race proved to be a good one for awhile at least. Dewey was riding his reputation as a war hero, while McKinley used the 5% unemployment and victory over Spain as campaign issues. Ironically, Dewey fired back by saying that the colonial war in the Philippines was unnecessary and too "European". As it came down to the wire, Dewey was gaining momentum as the war in the Philippines continued to see American soldiers die. Unfortunately for Democrats, a severe blunder would cost Dewey the Presidency. In early October, Dewey was quoted as saying that the Presidency would be easy because the President only follows orders from political bosses and congressional leaders. This would end any hope the Democrats had of securing the Presidency. Though Dewey would carry some Southern states, McKinley fairley easily won with 309 electoral votes to Dewey's 148 and. McKinley had won a second term.
1900 U.S Presidential election
William McKinley(Republican) - 53%
George Dewey(Democrat) - 42%
John G. Woodley(Prohibition) - 2%
Eugene Debs(Socialist) - 1%
Wharton Baker(Populist) - 1%
Others - 1%
[1] Theodore Roosevelt died in Cuba. 
Part 2: McKinley, Progressives, and Labor
Progressivism had been a rising political force in America since the 1890s. By 1900, it seemed poised to take force in the new decade. Slowly but surely, many Americans began to take anti-business stances as corruption and trusts began to come into the public light. By 1900, there had been a number of Progressives in the Republican Party. The growing number of Progressives in the party pushed for a Progressive in the ticket, but a pro-business conservative in Stephen Elkins received the nomination instead. Though McKinley agreed with Progressives on such things like civil rights, he and most Republican leaders were far from the Progressives in the business issue. The Republican establishment were pro-business and the Progressives were anti-business. The Republican establishment were anti-union, while Progressives supported compromise between business leaders and unions. President McKinley became even more of an anti-union leader when an Anarchist attempted to kill McKinley in September 1901. Luckily for McKinley, the would be assassin missed and was quickly tackled to the ground. The assassination attempt transformed President McKinley into a staunch anti-leftist. Though not even close to the far-leftism of Anarachist, McKinley blamed the less radical Progressives just as much as he did Anarchist and Socialist. As division between pro-business Republicans and Progressives deepened in 1902, a crisis was brewing that would rock the nation to it's core.
In early 1902, the United Mine Workers of America were threatening mine owners with a strike unless they recognized their union. Owners refused and a situation ripe for disastor sprouted up. Coal was absolutely necessary in heating cities during the winter. Without coal, many who lived in cities would freeze. Unfortunately, mine owners refused to recognize the UMWA as the representation of the workers. By June of 1902, nothing had been reached and most of the coal miners had went on strike. It is estimated that there were over 100,000 strikers. Progressives and Socialist supported the strikers in their quest for recognition. Most Republicans and many Democrats were not with the strikers. President McKinley was definitly not with them and by mid September, the Pennsylvania National Guard and the UMWA were close to conflict. By this time, President McKinley and Republican leaders feared massive Republican losses in Congress if the crisis was not fixed. Though Progressives pleaded for McKinley to negotiate a compromise between the UMWA and the coal mine owners, he would have none of it. Not only was President McKinley anti-UMWA, but Vice President Stephen Elkins was too. Though Elkins sympathized with Progressive on their discrimination, he was far from pro-UMWA. He himself was involved in the coal mining business in West Virginia. Elkins feared a radical UMWA uprising in his West Viriginian mines. Because of this and the overall massive anti-union oppinion of establishment Republicans, the Pennsylvania National Guard was told to end the strike and force the miners to work. On September 29th, the Pennsylvania National Guard opened fired on strikers. For three days battle would ensue. On October 1st, the dust had settled for the most part. In the end, 286 strikers were killed and many more injured. The "Miner War Massacre" would force most of the strikers back to work. A few of the immigrant workers were so mad, they packed their bags and left for their home country. The strike ended as a monumental defeat for all sides. The UMWA was not recognized and 286 of it's workers were killed. The Republican establishment were blamed for killing so many and supporting the mine owners. Both Democrats and Progressives lost the support of many laborers and unions for not doing anything monumental to support the strikers. Coal miner owners and the Pennsylvania National Guard were called killers. The only group that seemed to benefit from the massacre was the growing Socialist Party of America because the ineptitude of the Progressives and Democrats radicalized many unions and laborers. All in all, the "Mine War Massacre" proved to be benefitial to no party in congress. Election day came and passed, and frustration against the long dominating Republicans had finally come to fruition.
58th United States Congress(Senate)
Democratic Party: 48
Republican Party: 42
58th United States Congress(House)
Democratic Party: 195
Republican Party: 184
Populist-Progressive Party: 7
Well, on the bright side for establishment Republicans, they got rid of the Progressives as most moved to either the Democratic, Populist-Progressive, or Socialist parties. Unfortunately for the GOP, they were destroyed as expected. President McKinley now had to look foward to a Democratic congress and rising anger at Republicans.
The "Miner War Massacre" and the 1902 strike proved to be the worst of the Labor Wars in the decade. Other labor violence occured in San Francisco when 29 strikers died in 1903. The anger and frustration of workers led the American Federation of Labor to move towards the left. Unions and the AFL began to cooperate more with the rising Socialist Party as the Populist-Progressive Party would eventuallly fold in 1910 as workers and farmers slowly looked to Socialism. As for the government, the 58th congress proved to be uneventful. Besides a buildup in the Navy, nothing much was done except a few minor bills. All parties, meanwhile, looked to the 1904 Presidential elections.
Part 3: Parker takes the Presidency
Unlike some presidential elections, the 1904 election proved to be uneventful. Most knew the Republicans were going to lose and Democrats were going to win. The only question was who be the Democratic nominee. As for the Republicans, Vice President Stephen Elkins was nominated even though he knew he had a hell of fight in order to win. The Democrats wanted a balanced ticket of a moderate and a liberal. Scared of having a liberal take the Presidency, the Democrats nominated New Yorker Alton Parker. To gain some pro-union voters, the Democrats added William Randolph Hearst, as the Vice Presidential nominee. To no ones suprise, the Democrats easily won the election with 270 electoral votes. The Republicans won 198 electoral votes and the Populist-Progressives managed to get 8. The era of William McKinley was finally over.
President-elect Alton B. Parker

1904 U.S Presidential election
Alton B. Parker(Democrat): 54%
Stephen Elkins(Republican): 35%
William Simon U'Ren(Populist-Progressive): 6%
Eugene Debs(Socialist): 5%
Others: 1%<
59th United States Congress(Senate)
Democraric Party: 51
Republican Party: 38
Populist-Progressive: 1
59th United States Congress(House)
Democratic Party: 204
Republican Party: 170
Populist-Progressive: 11
Socialist: 1