I like Barack Obama.

I voted for him, worked on both of his presidential campaigns, and supported him in the 2008 primary. My first monetary donation to a political cause was to his first presidential campaign. While the Obama-Biden memes are pretty funny, I am genuinely sad to see him leave–and not just because of who his replacement will be.

This is not to say that he was perfect. Regardless of how bad the Republicans might be, Barack Obama deserves criticism. Progressives owe it to themselves to look critically at the soon-to-be former president.

But before I begin, two caveats: first, I am aware that the Democrats only had control of Congress for a small portion of Obama’s two terms in office. The ensuing criticisms take this into account, as it would be unfair to blame him for any mess created by congressional Republicans.

Second, President Obama’s position as a black man meant that he was forced to navigate boundaries that a white president would not have been. He had to carry not only the reputation of the Oval Office, but also his role as the first black president on his shoulders. I find it difficult quantify this in any way; but to ignore this seemed inappropriate.

While the list that follows is not exhaustive, it summarizes some of what I found to be the most disappointing moments of the Obama presidency:

• President Obama deported more undocumented immigrants than every president in the 20th century combined. His legacy toward undocumented immigrants is complicated, considering that he created programs to protected undocumented immigrants who came to the United States as minors, as well as their parents. However, his failure to stop mass deportations are a stain on his record.
• While unmanned drones surely will play a role in combat for the foreseeable future, the Obama administration used them in a destructive manner with little to no oversight. For every suspected combatant hit, 28 innocent civilians are killed. To make matters worse, the administration reportedly maintained a “kill list”, where U.S. citizens suspected of terrorism could be killed abroad without a trial.
• In 2011, President Obama supported a decision to limit the sale of emergency contraception to people under the age of 18. He referred to this as a “common sense measure” asserting that “most parents would probably feel the same way.” Most emergency contraceptive pills are less dangerous than a number of other sold over-the-counter drugs. His endorsement of respectability politics over reproductive health was a disappointment with wide-reaching effects for minors.
• Despite criticizing warrantless wiretapping under the Bush administration, President Obama seemed to overlook the National Security Administration’s data collection practices on his watch. At the very least, checks and balances and some tweaks to who exactly was collecting information would have mitigated this.
• The Affordable Care Act is the core of the Obama administration’s legacy, but is a deeply flawed piece of legislation. It is a huge work, but speaking broadly, it did nothing to break (or even weaken) the control of private insurance corporations–instead, it subsidized them! Despite supporting a single-payer healthcare system in the early 2000s, President Obama began deliberations for healthcare reform with the compromise of a so-called public option, which involved a government-run alternative to private health insurance. This compromised position was scrapped early on, paving the way for a watered-down, complicated piece of legislation that the Obama administration would proceed to poorly promote. The ACA has had some successes and its repeal is indefensible, but it has been a disappointment since its incarnation.
• While polling shows that President Obama has improved the image of the United States abroad, the administration’s Middle Eastern policy has been a bumpy road to say the least. Not all of the issues can fairly be blamed on President Obama, but the United States is still struggling to understand its position in the region.
• The Obama administration’s “war on whistleblowers” has led to the United States ranking 41st in the Reporters Without Borders’ World Press Freedom Index. For many people genuinely concerned about Donald Trump cracking down on freedom of the press, they can look to President Obama for setting that precedent.

Photo captured January 20, 2017.

Perhaps the largest disappointment of Obama’s presidency came from his own goals to reform the way that Washington D.C. operates. For candidate Obama, the partisan culture of Washington D.C.–not corporate money, not outside influence, not even necessarily corruption–was the main ill of the federal government. Pushing a progressive agenda was not his modus operandi. But even putting aside criticisms of Obama’s lofty goal, he failed on two fronts: what he did to fix Washington D.C. and what it is like now.

While President Obama was willing to compromise and work with congressional Republicans, he didn’t necessarily approach compromise in a productive manner. In normal negotiations, two (or more) sides come to the proverbial table with their ideal proposal and they work to reach some middle ground. When Obama negotiated, he would start by compromising, which continually put him in a weak position. He wanted to seem “above the political fray”, but by failing to aggressively defend his agenda, he also failed to bring about the change he so touted in 2008.

This aversion to politicking meant that Barack Obama failed to form effective relationships with lawmakers. Both Democrats and Republicans alike complained about his failure to work with Congress effectively. This may have been a symptom of Obama’s relative inexperience, but, to be frank, it impacted his ability to get stuff done.

Washington D.C. is more partisan and less functional today than it was when President Obama assumed office. A lot of dysfunction might not be his fault per se: then-Senate Minority Leader Mitch McConnell famously proclaimed, “The single most important thing we want to achieve is for President Obama to be a one-term president.” Virtually all of his GOP colleagues agreed.

However stubborn the Republicans may have been, it is only fair to judge President Obama by his own standards. He may have been a good president in other regards, but he was unable to accomplish his ultimate goal of reshaping the culture of Washington D.C. As a result of his belief in this goal, much of his legislative agenda couldn’t pass (again, not necessarily his fault), and what did pass was either deeply compromised or accomplished by easily-reversible executive orders. Furthermore, he leaves his party in post-election disarray without having given much post-election leadership.

All things considered, I will genuinely miss President Barack Obama. Democrats are right to reflect on the good parts of his time in office as the Trump administration gears up for action. But to forget the failures of the past eight years would be a failure in and of itself. In Obama’s final speech as president he modified his original slogan: “Yes we can; yes we did.” But, I think it’s fair to ask: did we really?

In Post Notes, I add some additional thoughts or context to a blog post I’ve previously written. That can be found here.