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The importance of self-awareness in presidential politics

Mitt Romney apparently thinks Jeb Bush's background in private equity might be a problem in the 2016 race.
Jeb Bush campains for Romney in Florida
Former Florida governor Jeb Bush delivers remarks on behalf of Republican presidential nominee Mitt Romney during a Small Business Victory Town Hall campaign...
As a rule, I don't have much use for the speculation as to who may or may not run in the 2016 presidential race. We'll find out soon enough, and until then, everything else is speculative and based on rumor.
This especially true of Mitt Romney -- remember him? -- who seems to be rewarded every few weeks with a series of new "he might try again!" reports in major outlets.
But once in a while, it's worth making an exception. This new Politico piece, for example, reports that Romney is unimpressed with those likely to run in the Republican primaries and is suddenly "open to the idea" to running a third time, following failed bids in 2008 and 2012.
The piece includes a lot of unsourced quotes from "people who've spoken to" Romney -- which is to say, take all of this with a grain of salt -- but this tidbit amazed me.

[Romney] has assessed various people's strengths and weaknesses dispassionately, wearing what one ally called his "consultant cap" to measure the field. He has said, among other things, that Jeb Bush, the former Florida governor, would run into problems because of his business dealings, his work with the investment banks Lehman Brothers and Barclays, and his private equity investments. "You saw what they did to me with Bain [Capital]," he has said, referring to the devastating attacks that his Republican rivals and President Barack Obama's team launched against him for his time in private equity, according to three sources familiar with the line. "What do you think they'll do to [Bush] over Barclays?"

Romney believes his campaign struggled in part because of his controversial private-sector background. He also believes Jeb Bush would be susceptible to similar criticisms in 2016, which is true.
But it's that next part that I can't quite wrap my head around: if Bush would struggle because of his financial-sector work, why on earth would Romney run again and invite the identical attacks on himself? Because this worked out so well the last time around?
The article got a response from a Bush ally.

Another top Republican operative who is supportive of a Jeb Bush candidacy said that he did not believe Bush would have as much trouble with his financial dealings in a campaign as Romney did. "Jeb's wealth and investments are nothing on the scale of Romney's. He is not building car elevators," this person said, offering a hint of the bitterness that could ensue if both Romney and Bush run.

Oh good. Before the campaign gets underway in earnest, there's already a quiet argument underway about which Republican's vast private-equity wealth will be more politically damaging to their ambitions.