A tally of Jeb Bush’s many lucrative board positions and consulting gigs paint a complicated picture of the former Florida governor’s chances at surviving a campaign for the White House. The report, by The New York Times, offers a look at a man who felt his wealth had been diminished by being governor of the country’s fourth most populous state, a perceived wrong he’s been busy righting since he left office in 2007.

According to the Times, Bush has worked for or with Lehman Brothers, a soap maker whose books were cooked, and an Affordable Care Act-supporting hospital owner. He has raked in at least $3.2 million from board positions, charges $50,000 for speeches, and is said to be paid more than $1 million a year by Barclays, the firm that absorbed much of Lehman after Bush’s bid to have Mexican billionaire Carlos Slim Helú save the failing bank.

He’s made so much money, in fact, that one Bush supporter went on the record with the paper to cast doubt as to whether or not the presumptive candidate would even want to pause the gravy train to run for president.

“Although he’s been at this for seven years, it’s the last few years that he’s begun to flourish as an investor and build a commendable nest egg,” longtime ally Al Cardenas told the Times. “Leaving all of that behind, all he’s built, is a challenge and a sacrifice for him.”

The Republican picture for 2016 is quite murky, with would-be front-runners such as New Jersey governor Chris Christie embroiled in scandals, and upstart challengers like Kentucky senator Rand Paul scandalizing the party with unorthodox platforms (Paul is unapologetically isolationist, for example). Florida senator Marco Rubio, Texas governor Rick Perry, former senator Rick Santorum, Wisconsin governor Scott Walker, and Ohio governor John Kasich have also been rumored to be mulling bids.

Bush fared particularly well at billionaire donor Sheldon Adelson’s Las Vegas retreat in March. The event, dubbed the “Adelson primary” but ostensibly organized for the Republican Jewish Conference, saw Bush speak in a private airplane hangar. The former governor managed not to offend Adelson or the pro-Israel crowd’s sensibilities, which Christie ran afoul of by using the accurate phrase “occupied territories” to refer to Palestine.

“The notion that Jeb Bush is going to be the Republican presidential nominee is a fantasy nourished by the people who used to run the Republican Party,” wrote Buzzfeed editor Ben Smith, noting that Bush’s insistence on federalized education and immigration reform will be difficult, if not impossible, to square with today’s Republican base. Bush has gone as far as to refer to undocumented immigrants entering the United States illegally as committing “an act of love,” and “an act of commitment to your family,” language that doesn’t really gel with the sometimes fiercely anti-immigrant rhetoric coming out of the G.O.P.

After deciding not to run in 2012, Bush himself seemed to feel as though what he described as his “window” was closing. “Given kind of what I believe and how I believe it, I’m not sure I would have been successful as a candidate, either,” Bush told CBS This Morning. “These are different times.” If Bush does run and is ultimately felled by his business associations, he will join the much wealthier Mitt Romney as among the few American politicians who appear too rich to win high office.