In a first-ever endorsement of a caucus candidate after Iowa became a player in presidential politics, the 1988 editorial board of the Des Moines Register opted to lead public opinion, urging Democrats to support a non-establishment Midwestern candidate, Sen. Paul Simon. Twenty-eight years later, the state's newspaper of political record flip-flopped, choosing to follow the prevailing winds of the Eastern Democratic establishment, with an odd effort to boost the former senator from Wall Street, Hillary Clinton.

"What the record shows is a man who has decent instincts and who sticks by them. Simon exudes a simple trustworthiness." Those were the 1988 Register board's words supporting Sen. Simon. Contrast them with the tepid touting of Ms. Clinton this year: "In the final analysis, Iowa Democrats will have to choose between the lofty idealism of Bernie Sanders and the down-to-earth pragmatism of Hillary Clinton. For some, this will be a choice of whether to vote with their hearts or their heads."

I remember well the impact of the Register's endorsement of Simon. I was his press spokesman. It revived our campaign in the caucuses; we fell just a few points short of defeating Rep. Dick Gephardt. The ambitious Missouri congressman was flipping and flopping between his pro-business, pro-Wall Street positions in Washington and his new-found, pro-union populism in Iowa. The Register had this to say about Gephardt: "[He] may be the most disappointing of the field" and "his vision for America is too narrow."

That compares to the 2016 Register's less than enthusiastic support for Clinton: "She is not a perfect candidate, as evidenced by the way she has handled the furor over her private email server. In our endorsement of her 2008 campaign for president, we wrote that ‘when she makes a mistake, she should just say so.' That appears to be a lesson she has yet to fully embrace." Their recent editorial continued: "Her changing stance on gay marriage, immigration and other issues has invited accusations that she is guided less by personal conviction than by political calculations. She refutes that, and argues persuasively that a willingness to change one's thinking on specific issues, while remaining true to what she calls ‘the same values and principles,' is a virtue, one lacking in most politicians."

Well, it was a virtue in the eyes of the 2016 Register editorial board anyway, beholding Secretary Clinton's most recent incarnations on the issues.

The world changes, politics and journalism included. Is the Register liberal or conservative, Democrat or Republican? It was for Richard Nixon in the 1972 general election, then Jimmy Carter in 1976. It supported Barack Obama in 2008, but flipped to Mitt Romney in 2012. Now advocating Clinton over Sanders, the paper revealed its pragmatic self. In 1988, it showed idealism, for a principled public servant from Illinois over a practical politician from Missouri.

Like politicians who try to please most of the people most of the time, the Register is conflicted between pragmatism and idealism. When pragmatic, its endorsement usually changes few minds. But when it chooses to be idealistic, the paper can have influence.

Had the handful of men and women who make up the editorial board decided to risk siding with the Democratic socialist Bernie Sanders' call for a political revolution, the Des Moines Register might have impacted the 2016 caucuses. By playing it safe, they let their and other newspaper endorsements slip further into the dustbin of journalism history. Perhaps that is where they belong.

Though claims of support from the grave are risky, I have no doubt who Paul Simon -- a man I was privileged to know for 37 years before his death in 2003 -- would be endorsing in 2016. His name is Bernie. May Paul, and the Register's endorsements, R.I.P.

