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I'm not trying to defend Obama, especially I abhor his drone warfare, but politics is known to be cut throat, and politicians are beholden to campaign donations. Election campaigning is an expensive endeavour, and those who could throw more money have increased likelihood of winning. There are exceptions to the rule of course, and sometimes those who spent less still wins, but the candidate increases his/her chances of winning by having more campaign funds.
With all that said, this means playing ball with the campaign donors and their lackeys, or else they will gang up on you. Obama is all too aware of this. Consider that Lena Khan's aggressive FTC investigations under Biden on tech giants pissed off the oligarchs. Musk, Zuckerberg and Bezos threw their weights on supporting Trump and now we are here. Apparently, Obama told Bernie in 2016 that he "can't be the president and be the good guy".
What is required is someone who is not afraid dip their hands into the mud and throw some, without being in the mud pit itself. People villainise Machiavellianism for good reasons, but evil don't play by the rules and evil never sleeps. Why still be nice if they already stabbed you? You definitely need to be Machiavellian when the situation requires it. We had that with the Roosevelts, and the fact that they were already wealthy insulated them from being beholden to the whims of campaign donations of the oligarchs and their attack dogs, made them have more free reign to pursue actually more progressive policies. Some people say JB Pritzker has those qualities-- an already wealthy politician willing to be Machiavellian to pursue progressive policies, although I don't know much about the man to warrant the observation.
Edit: JB not Joseph Pritzker