The Biggest Mistake of Obama’s Presidency?

by Nathan L. Gonzales September 10, 2013 · 10:01 AM EDT

President Barack Obama could have saved himself a lot of headaches, and potentially his presidential legacy, if he had done one thing: cultivated a relationship with Congress.

It doesn’t have anything to do with courting GOP leadership or caving to tea party conservatives. Multiple congressional Democrats believe the White House would be in a better position today if the president had made more of an effort to communicate with Democrats on the Hill from the beginning.

“When the stakes are high, negotiations are easier and smoother if there is a level of trust already established, ” one Democratic operative said.

Now Obama is in a precarious political position on Syria. He has asked members of Congress to take a potentially unpopular vote when many on Capitol Hill, even those within his own party, don’t entirely trust him or believe that the White House will offer adequate cover to those who support the president’s request.

The current situation isn’t the only time a better relationship with Congress would have been helpful.

In the first year of his presidency, Obama chose to take a hands-off approach to his health care measure. As a result, the bill took over a year to get done, the president didn’t spend a lot of time “selling” it after it passed, and the subsequent unpopularity contributed to Democrats’ losing 63 seats in the House in the 2010 elections.

While health care continues to get the most attention, many House Democrats still feel most burned by the so-called cap-and-trade bill from 2009.

According to Democratic operatives, many House members felt as if they walked the plank on the environmental bill — they voted for it, but when they turned around to look for support, there was little. The bill failed to pass the Senate, the White House wasn’t out selling the legislation, and a total of 52 House Democrats sacrificed their seats in 2010 (albeit not all of them voted for the bill). “It set the tone badly,” one House strategist said about the first year of the president’s first term.

Now there’s less incentive for fellow Democrats to follow on something as controversial as a military assault on Syria because they haven’t had much in the way of Obama’s support in the past. Earlier this year, the president might have gotten the benefit of the doubt on intelligence gathering if there had been more communication with the Hill previously.

In short, if the president had engaged members of Congress from the beginning of his tenure, even behind closed doors, some of his most challenging political moments could have been an easier lift. Democrats might even still be in the majority in the House if the health care and cap-and-trade bills had been handled differently. And that certainly would have an effect on the legacy that Obama leaves behind.