This site offers a long list of historic firsts for President Obama. None of them are anything he should be proud of. I'll list a few examples but you should really take a look at the site to see the whole list.
• First President to Violate the War Powers Act (Unilaterally Executing American Military Operations in Libya Without Informing Congress In the Required Time Period – Source: Huffington Post)
• First President to Use the IRS to “Unfairly Target Political Enemies” as Well as Jewish Groups (Source: Sen. Ted Cruz)
• First President to Arbitrarily Declare an Existing Law Unconstitutional and Refuse to Enforce It (Defense of Marriage Act – Source: ABC News)
• First President to Intentionally Disable Credit Card Security Measures (in order to allow over-the-limit donations, foreign contributions and other illegal fundraising measures – Source: Power Line)
• First President to Preside Over a Cut to the Credit Rating of the United States Government (Source: Reuters)
• First President to Sign a Law Requiring All Americans to Purchase a Product From a Third Party (Source: Wall Street Journal)
• First President to Attempt to Bully a Major Manufacturing Company Into Not Opening a Factory in a Right-to-Work State (Boeing’s facility in South Carolina – Source: Wall Street Journal)
And these are but a few of his firsts listed in the article.