The "retroactive retirement" Romney finalized with Bain Capital, in 2002, claimed February 1999 as his exit date. For three years, Romney got to enjoy the perks of being the boss, including an annual salary of at least $100,000, as well as investment opportunities, and, presumably, the authority to intercede in Bain deals if he chose to, whether or not he actually exercised that power. He also held open the option of returning as boss and owner after the Olympics, if he wanted to.
He got all of that, while being absolved in the end of all responsibility and blame for anything the company did during that time.
The ability to fashion that kind of no-lose arrangement, frankly, is one way that the very wealthy and powerful differ from the rest of us. When revealed, it can make successes look inevitable, rather than impressive.
If Romney's history of stacking the deck is subject to scrutiny, it could undermine the accomplishments at the core of the argument for his candidacy.
Bain Capital, for instance, often structured its deals as no-lose propositions: Bain extracted enormous fees and contracts from its takeover targets, making millions even when those companies collapsed.
And Romney has applied the principle to his own carefully guarded personal image for decades.
One of the most blatant was his pre-arranged face-saving plan when he agreed to head Bain Capital in the first place, in 1983.
In a tale first revealed by Boston Globe reporters in 2007, Romney agreed to do it only if his boss at Bain & Company, William Bain, ensured that there was, in Bain's words, "no professional or financial risk."
If Bain Capital failed, Romney would reclaim his old job and salary, plus any raises he would have received. Plus, Bain agreed to "craft a cover story," the Globe wrote, to shield Romney from personal blame for Bain Capital's failure.
It seems very likely that this is more-or-less how Romney arranged his leave of absence for the Olympics. It makes for curious bookends to his career at Bain Capital: he started by pre-arranging a way to avoid responsibility, and ended by retroactively arranging to avoid responsibility.
If so, it doesn't make Romney sound like the bold turnaround master he claims to be. And it raises the question: what else in his life is as he claims, and what is just a pre-arranged "cover story"?
The secrecy and deception make it hard for voters to judge how much credit — or blame — Romney really deserves for Bain, or the Olympics, or his time as governor. It also suggests that a Romney presidency would be even more opaque than most.
The Shadow Years loom large with Romney because they fall within a time when his investment activity was particularly complex and wide-ranging — and open to criticism.
In earlier years — when both the leveraged buyout field, and Bain Capital itself, were newly developing, Bain Capital tended to get involved in fewer, fairly straightforward deals.
And after 2002, Romney placed his investments in a blind trust prior to taking the oath of office as governor. That has allowed him to wave off questions about his holdings since then. (Although Romney had previously derided the idea that a blind trust absolved Senator Ted Kennedy of responsibility, and Romney's trust is considerably less "blind" than most.)