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Honor the Troops, Question the War

05/14/2015 10:25 am ET | Updated May 14, 2016

In the fall of 2004, as I was in the intensity of the re-election campaign of President Bush as chief strategist, I had to take a drive that was one of the hardest drives I have ever taken. About a week before Election Day, my oldest son jumped in the passenger seat of my Dodge pickup truck with a green duffle bag.

I drove him to the Army post in Arlington, Virginia, a few miles from Bush-Cheney headquarters, where he was going to get transportation to go to boot camp in South Carolina.

I hugged him tight, told him I loved him and was very proud of him, and wished him Godspeed. I stayed as strong as I could and put my sunglasses on so he couldn't see the tears in my eyes, jumped back in my truck and drove to the headquarters shaking my head.

I had just put my son in the hands of the Army and was about to help re-elect the person who would ultimately send him into harm's way. Wow.

In Daniel's five years of service, he was in Iraq for about 14 months, and served his country well. He was as proud of his time as I was, but both of us over time began to question the decision to go to war. And so has nearly every single service member I have talked to in the time since.

I have come to the place where I believe the decision to go into Iraq was a huge mistake. Should have I asked more questions in the midst of all that? Yes. Should I have not have placed trust in the administration that they knew what they were doing? Yes. Can we honor our troops and still be opposed to this war decision and seek answers? Absolutely.

It is astonishing to me watching former Governor of Florida Jeb Bush lay out a confusing and convoluted answer to the questions surrounding the Iraq war. Of any question that you should be prepared to handle as the brother of the president who led us into this folly, this is one you should have thought about, soul-searched and come up with a clear and concise answer.

First, Jeb "misheard" the question and answered that he would have gone to war even knowing what we know today. Second, understanding this position is just not tenable with the loss of life and trillions of dollars while leaving the Middle East more unstable, Jeb said, yes, mistakes were made but he didn't know what he would do at this time and this is a hypothetical question. Now, he is saying even asking the question is doing a "disservice" to those who served.

The best way to honor our servicemen and women is to have a leader who clearly understands history, is willing to account for mistakes even if they are by a relative, and then annunciate how he would do things differently. People who fight for our flag and make this sacrifice want to believe that the truth matters, that government can be trusted and that leaders know what they are doing.

President John Kennedy re-examined his decision regarding the Bay of Pigs fiasco and learned. He was able to implement this learning in the handling of the Cuban Missile Crisis. That is what leadership does.

Jeb and his campaign need to figure out that nearly every single question related to running for president is a hypothetical question. You aren't president yet, so folks want to know what you would do about various circumstances and situations. What would you have done differently from the past, and how does that inform what you would do going forward.

We are all trying to gain insights into the kind of leader you would be if you are elected. By its very nature, a presidential campaign is hypothetical.

And I hope we can get to the point where, by raising questions either from the media or regular voters, we don't question people's patriotism. My son served with great distinction and believes he did what his country asked of him, but he also thinks we should acknowledge we messed up. Honoring him and all the other folks both living and dead is best done by an open and honest discussion about this monumental decision.

There is nothing more important a president will do than taking our country into war.

I am sure Jeb's campaign will clean this up, or try the best they can, but it does tell us they were ill-prepared for probably the most fundamental question he would be asked in the course of the pursuit of his presidency. And I hope there clean up isn't just an effort to attack the other side or question the motives of folks asking questions. Conducting a campaign in that manner does a disservice to all voters, both military and civilian.

There you have it.

Matthew Dowd, founder of ListenTo.Us, is an ABC News analyst and special correspondent. Opinions expressed in this column do not reflect the views of ABC News.