Is Jeb Bush’s show of transparency working?

For Jeb Bush, the catchword continues to be “transparency.”

The Republican presidential candidate is set to release 33 years of tax returns online Tuesday afternoon, a move that would set a new record in terms of financial documents made public by a politician.

The disclosure would give voters a clearer picture of Mr. Bush’s wealth and could be part of a plan to distinguish him from both opponents and predecessors in the race for the White House. It’s also a political strategy that Bush has long employed – to questionable success.

“This is more than any presidential candidate in the history of the United States,” Bush spokeswoman Allie Brandenburger told CNN Tuesday morning. “This display of transparency is consistent with the high level of disclosure he has practiced during his life in public office.”

True enough, the only other candidate to have disclosed tax documents on such a scale was former Kansas senator Bob Dole, who had released nearly 30 years of tax returns by the time he ran for president in 1996. And Bush has shown that he is willing to open up: In February, the former Florida governor published eight years of uncensored emails from his time serving in the Sunshine State.

For some, the release first of his emails and now of his tax returns are a sign that Bush understands the present political and media environment.

“You don't have to pay much attention to politics to know that people distrust (and often dislike) the people representing them,” Washington, D.C. correspondents Chris Cilliza and Aaron Blake wrote for the Washington Post in January. At the same time, they added, “the ability of politicians to hide unsavory tidbits of their professional and personal lives is almost totally nonexistent.”

By getting ahead of any accusations about his personal life or finances, Bush is defusing some of that distrust and suspicion, Mr. Cilliza and Mr. Blake wrote.

“What he’s saying is, in essence: If I was a crook, would I let you see all the evidence that proves it?” they continued. “Jeb is playing the transparency card right – and at the right time.”

History has shown that the strategy could work. While running for vice president alongside Dwight Eisenhower in 1952, Richard Nixon countered a brewing scandal over his finances by laying out his personal financial information in a nationwide broadcast now known as the “Checkers speech,” Forbes reported.

Though it didn’t exactly start a trend of financial disclosures, the speech was a political success: Mr. Nixon remained on the Republican ticket, and he and Mr. Eisenhower went on to win the election.

Things have changed plenty since the 1950s, however. Skeptics have pointed out that politicians’ financial disclosures today hardly provide the public a complete picture of their relative wealth. Richard Rubin, tax policy reporter for Bloomberg, reported:

Candidates report assets’ value in ranges so broad that they can be virtually meaningless. Their homes, cars and federal retirement plans are generally off limits from public view. Nor are presidential contenders subject to rules that make members of Congress disclose stock transactions within 45 days and reveal who holds their mortgages.

Income tax forms do provide more details about a candidate’s charitable contributions, investments, and foreign holdings, but even those “don’t necessarily present a full picture of someone’s wealth,” Mr. Rubin wrote.

Still, Bush seems to understand the importance of tax transparency – or at least the perception of it – when it comes to getting a leg up over others in a presidential race. As Forbes reported:

Nixon used his Checkers speech to turn the tables on his Democratic rivals. His openness even gave him enough credibility to resist calls for further disclosure.

When done right, in other words, transparency can be unpleasant for candidates. But it can also be very useful.