So to construct a steelman argument for an opposing position (leftism in my case) is to apply Dennett/Rapoport Rules for kindness in criticism.
First, what is leftism? Left-wing politics is a range of political positions described as follows (excerpting at least a few main points; for the full discussion consult the link):
Left-wing politics supports social equality and egalitarianism, often in opposition to social hierarchy.[1][2][3][4] It typically involves a concern for those in society whom its adherents perceive as disadvantaged relative to others (prioritarianism) as well as a belief that there are unjustified inequalities that need to be reduced or abolished (by advocating for social justice).[1] The term left-wing can also refer to "the radical, reforming, or socialist section of a political party or system".[5]
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The following positions are typically associated with left-wing politics.
Economics
Leftist economic beliefs range from Keynesian economics and the welfare state through industrial democracyand the social market to nationalization of the economy and central planning,[27] to the anarcho-syndicalistadvocacy of a council- and assembly-based self-managed anarchist communism. During the industrial revolution, leftists supported trade unions. At the beginning of the 20th century, many leftists advocated strong government intervention in the economy.[28] Leftists continue to criticize what they perceive as the exploitative nature of globalization, the "race to the bottom" and unjust lay-offs. In the last quarter of the 20th century, the belief that government (ruling in accordance with the interests of the people) ought to be directly involved in the day-to-day workings of an economy declined in popularity amongst the center-left, especially social democrats who became influenced by "Third Way" ideology.
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Social progressivism and counterculture
See also: Socialist feminism and Socialism and LGBT rights
Social progressivism is another common feature of modern leftism, particularly in the United States, where social progressives played an important role in the abolition of slavery,[75] women's suffrage,[76] civil rightsand multiculturalism. Progressives have both advocated prohibition legislation and worked towards its repeal. Current positions associated with social progressivism in the West include opposition to the death penaltyand the War on Drugs, as well as support for legal recognition of same-sex marriage, cognitive liberty, distribution of contraceptives, public funding of embryonic stem-cell research and the right of women to choose abortion. Public education was a subject of great interest to groundbreaking social progressives, such as Lester Frank Ward and John Dewey, who believed that a democratic system of government was impossible without a universal and comprehensive system of education.
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Varieties
The spectrum of left-wing politics ranges from center-left to far-left (or ultra-left). The term center-left describes a position within the political mainstream. The terms far-left and ultra-left refer to positions that are more radical. The center-left includes social democrats, social liberals, progressives and also some democratic socialists and greens (including some eco-socialists). Center-left supporters accept market allocation of resources in a mixed economy with a significant public sector and a thriving private sector. Center-left policies tend to favour limited state intervention in matters pertaining to the public interest.
Now, before I get to the "can it be steelmanned" question, I would like to ask:
Take your median individual on the leftism spectrum as characterized above, assume a high level of education/schooling and then ask that person to make an attempt to steelman a position that such a person would typically hold in contempt. Let's not make it an easy-to-hate case like right-wing authoritarianism, fascism, Nazism or similar theories. Let's make it a less-easy-to-hate position held by a median person on the American right, perhaps a regular listener of the Rush Limbaugh show, reader of Thomas Sowell . . . or is that too not-easy-to-hate? Let's make it, instead, a person also within the "mainstream" of the American right who holds beliefs widely held among Republicans that are or may be easily open to ridicule: opposition to evolutionary theory and/or belief that humans appeared in their present form less than 10,000 years ago; belief that Sarah Palin is qualified to be president; belief that Muslims and sharia law pose an existential threat to the nation; belief that foreigners are invading and taking highly valued jobs from native citizens; belief that the mainstream media is irredeemably biased and unreliable while Fox News is the height of journalistic reliability and virtue; belief that Democrats now are seeking to legalize infanticide on demand; these sorts of things.
(There's also an intellectual perspective that a median leftist seems to hold in great contempt, but based on a strawman (see above) conception of that perspective: Ayn Rand's Objectivism. Said intellectually-lazy contempt is a good explanation for why I hold the typical leftist in contempt.)
Now, is it reasonable to ask a median leftist or Democrat to steelman the views of said Republican? Because that's not altogether different from asking me to steelman leftism. Okay, so some of the views described in the quoted section above - namely those within the "social progressivism" section resonate with me as a libertarian who rejects typically 'conservative' conceptions of the state as a vehicle for soulcraft/virtue-cultivation.
But note that I did narrow down the sort of American-mainstream rightist a median leftist would hold in contempt to something fairly definite; I didn't put it to this hypothetical leftist to steelman "rightism." So perhaps I should narrow down my conception of leftism for steelmanning purposes to something more specific and definite, and preferably to one that I would hold in least contempt -- i.e., the most philosophically fortifiable version of leftism that might exist, and one that still in some fashion plausibly falls within the boundaries of the range of left-wing views described above.
And once you narrow it down that way, it comes to something like: a pro-capitalism (obviously not the laissez-faire version, but still private ownership of industry), pro-market, center-left, pro-safety-net, proactively-anti-discrimination, socially libertarian, swing- or purple-state Democrat type, probably more in line with a (non-Crooked) Hillary Clinton type as opposed to a Crazy Bernie Sanders or more-clever-than-wise AOC type for whom I have much contempt qua political figures. (So they're not as bad as Stalin, Mao, or Castro. Their proposed shit sandwich is democratic, after all, which is, um, less worse than those fuckers. So a majority rather than a dictator owns your life; just wonderful.) And then imagine such a position as defended not by Crooked Hillary but by the most worthy philosophical figure that might advocate it. Someone that Aristotle could take seriously.
Thus narrowed down, the name 'John Rawls' comes first to mind. (If not him, then, say, a collection of editorial board members at Ethics or Philosophy & Public Affairs, many of whom would also be household names in a rational polity.) So, can the Rawlsian position be steelmanned more than he basically did on his own behalf already? Doubtful, but that may be the most philosophically-fortified version of left-wing thought within the range given above. If Democrat politicians and Democrat-dominated mainstream media were fluent in Rawls (as they should have been if their liberal arts schooling was worth what it's supposed to be), they would look a lot more formidable than the bunch of clowns they look like right now. It would necessitate an intellectual-arms-race response from the right, which is to say that the likes of Rand and Nozick would become more prominent in the national discussion, for a real high-level dialectic within a philosophically-educated citizenry to finally take place. (Would that be too fucking much to ask? Isn't it what Aristotle would want to see, ffs?) Then we'd see how well Rawls fairness-intuitions reflected in his Original Position device fares against the 'your-life-belongs-to-you-not-the-polity' intuitions-plus-theory of Rand, Nozick, et al. (Assume the likes of an Oakeshott or Scruton to represent the conservative perspective. Surely the wildly intellectually diverse academy gives them their due coverage, ffs?) (Also assume widespread familiarity with the quasi-Aristotelian-essentialist metaphysics (with reason/intellect as the human essence) underlying Rand's ethical-political standpoint, and hence her central "role of the mind in man's existence" theme, ffs already.)
Now, as a libertarian, anything with -libertarian as suffix might naturally stimulate my interests. And so any left-position that calls itself left-libertarianism (represented by Otsuka, Steiner, Vallentyne, and Van Parijs) might be another steelman-able left-wing position. Somehow it hasn't exactly stimulated my interest enough to investigate all that deeply; perhaps it's the emphasis on a fair initial distribution of "resources" when (as per Rand) the mind/intellect is the ultimate resource for generating value-added, that seems to miss the key and central point of what motivates Rand-style right-libertarianism. But this is an area where I have homework to do as time and interest allow; the art or science of eudaimonia (with social entailments of that, including supportive (non-state) institutions) is a larger fish to fry at the moment. At the base of that art/science is cognitive/intellectual perfectionism, and hence (better living via) philosophy. (And my current fish-frying involves an intensive inductive survey of historical philosophical activity as exemplified in such concrete figures as Plato and Aristotle; and so next up on my reading list is the Oxford Handbook of Hume, the Oxford Handbooks being eminently useful resources for the subject matter they cover. After the Hume one it'll probably be the Hegel one.)
So even as much as this or that political viewpoint could be steelmanned, does that generate as much bang for the human-situation-improvement buck as constructing a steelmanned program of philosophical living? That way our polity can finally have that worthwhile dialogue about which political philosophy is strongest -- assuming everyone isn't already too busy flourishing to spend time figuring out the best way to use coercive institutions on one another. Philosophy (beginning at the youngest feasible age), goddammit.
