Theodore Roosevelt was, as he himself claimed, a friend of the working man.  All the same, he did not accept labor’s view of the world uncritically, and he expected of organized labor and of the individual working man the same things that he expected from everyone else (including himself): honest dealings, hard work, fair play and a sense of patriotism, or at least adherence to American ideals (as he defined them.)  In other words he did not automatically side with or against labor in the many disputes that characterized that era, but it can fairly be said that he did more for working class people than any president before him had ever done, and, given the changes that took place in later years, as much as almost anyone who succeeded him, with the exception of his cousin, FDR.

In the following passage from a 1911 magazine article TR talks about collective bargaining:

One of the prime objects which the Progressives have in view in seeking to secure the highest governmental efficiency of both the National and the State Governments is to safe-guard and guarantee the vital interests of the wage-workers.  We believe in property rights; normally and in the long run property rights and human rights coincide; but where they are at variance we are for human rights first and for property rights second.  Lincoln phrased it in one of his homely anecdotes when he said, "We are for both the man and the dollar; but if we must choose between them, we put the man above the dollar"; and in a more formal speech, when be said: "Labor is the superior of capital, and deserves much the higher consideration." …

At the outset let me make clear one point.  I have no sympathy with any limitation of efficiency, no sympathy with any provision which seeks to reduce the work of the high-grade man to the level of the low-grade man.  The very fact that I so emphatically believe in the high dignity of manual labor, and desire to do all in my power to raise its position as compared with merely mental labor, gives the reason why I feel we should welcome high skill in manual labor, extreme efficiency therein, just as we recognize skill and efficiency in any form of mental labor.  Unless there is pride in efficiency in any line of work that work will never stand high in the popular estimation.  If all that a man desires is to get through his job with the minimum of effort and skill on his part, then he will never have, because he will never deserve, the respect of his fellows. ...

... In order to raise the status, not of the exceptional people, but of the great mass of those who work with their hands under modern industrial conditions, it is imperative that there should be more than merely individual action.  The old plea that collective action by all the people through the State, or by some of them through a union or other association, is necessarily hostile to individual growth has been demonstrated to be false.  On the contrary, in the world of labor as in the world of business, the advent of the giant corporation and the very wealthy employer has meant that the absence of all governmental supervision implies the emergence of a very few exceptionally powerful men at the head and the stamping out of all individual initiative and power lower down.  Unrestricted individualism in violence during the dark ages merely produced a class of brutal and competent individual fighters at the top, resting on a broad foundation of abject serfs below.  Unrestricted individualism in the modem industrial world produces results very little better, and in the end means the complete atrophy of all power of real individual initiative, real individual capacity for self-help, in the great mass of the workers.

There must, therefore, be collective action.  This need of collective action is in part supplied by the unions, which, although they have on certain points been guilty of grave shortcomings, have nevertheless on the whole rendered inestimable service to the working man.  In addition, there must be collective action through the government, the agent of all of us.

Probably the chief obstacle in the way of taking such wise collective action lies in the mental attitude of those who still adhere to the doctrinaire theory of eighteenth-century individualism, and treat as a cardinal virtue the right to absolute liberty of contract--and of course, carried out logically, the theory of absolute liberty of contract simply means the legalization of all kinds of slavery.  It is essential that the nation and the State should be able to forbid the exercise of that kind of pseudo-liberty which means the abridgment of real liberty.  There has been a steady growth in these matters, and views which a century ago the courts accepted as almost axiomatic are now upset in decision after decision.  The Supreme Court of the United States on January 3 last stated the case as regards liberty of contract as follows: "There is no such thing as absolute freedom of contract.  The power of government extends to the denial of liberty of contract to the extent of forbidding or regulating every contract which is reasonably calculated to injuriously affect the public interest." The decision goes on to state that the power of the United States is absolute as regards regulating commerce between the States. ...

... Wages and other most important conditions of employment must remain largely outside of governmental control and be left for adjustment by free contract between employer and employee, with the important proviso that there should be legislation to prevent the conditions that compel men and women to accept wages that represent less than will insure a decent living.  But the question of contract between employer and employee should not be left to individual action, for under modern industrial conditions the individual is often too weak to guard his own rights as against a strongly organized body or a great capitalist.  In the present state of society, and until we advance much farther than at present along lines of genuine altruism, there must be effective and organized collective action by the wage-workers in great industrial enterprises.  They must act jointly through the process of collective bargaining.  Only thus can they be put upon a plane of economic equality with their corporate employers.  Capital is organized, and the laborer can secure proper liberty and proper treatment only if labor organizes also. 

It is, I trust, unnecessary to say that the most emphatic recognition of this need does not mean any condonation of whatever is evil in the practices of labor organizations.  Labor organizations are like other organizations, like organizations of capitalists; sometimes they act very well, and sometimes they act very badly.  We should consistently favor them when they act well, and as fearlessly oppose them when they act badly.  I wish to see labor organizations powerful; and the minute that any organization becomes powerful it becomes powerful for evil as well as for good; and when organized labor becomes sufficiently powerful the State will have to regulate the collective use of labor just as it must regulate the collective use of capital.  Therefore the very success of the effort we are making to increase the power of labor means that among labor leaders and among other citizens there must be increased vigilance and courage in unhesitatingly rebuking anything that labor does that is wrong.