Two weeks after the 2014 midterm elections, then-President Barack Obama addressed the nation on the issue of illegal immigration. Part of this address -- delivered from the White House -- actually focused on the negative aspects of people illegally entering and staying in the United States.
"But today, our immigration system is broken -- and everybody knows it," Obama said.
"Families who enter our country the right way and play by the rules watch others flout the rules," he said. "Business owners who offer their workers good wages and benefits see the competition exploit undocumented immigrants by paying them far less. All of us take offense to anyone who reaps the rewards of living in America without taking on the responsibilities of living in America."
Obama then claimed he had made progress in securing the border.
"When I took office, I committed to fixing this broken immigration system," he said. "And I began by doing what I could to secure our borders. Today, we have more agents and technology deployed to secure our southern border than at any time in our history. And over the past six years, illegal border crossings have been cut by more than half."
According to the Pew Research Center, when Obama was sworn into office in 2009, there were 11.3 million unauthorized immigrants in the United States. Over the next two years that increased to 11.5 million. Then, during Obama's final six years in office it modestly declined, hitting 10.5 million in 2017, the first year of President Donald Trump's first term.
In his Nov. 20, 2014 address, Obama vowed to focus immigration enforcement on those who posed "actual threats to our security."
"(W)e'll take steps to deal responsibly with the millions of undocumented immigrants who already live in our country," Obama said.
"And that's why we're going to keep focusing enforcement resources on actual threats to our security," he said. "Felons, not families. Criminals, not children. Gang members, not a mom who's working hard to provide for her kids. We'll prioritize, just like law enforcement does every day."
Did Obama's policy work?
On Aug. 25, 2015, nine months after Obama delivered this address to the nation, Manuel Alberto Cortes Cuan, a Mexican citizen who had already been deported four times during Obama's presidency, was deported for a fifth time.
In a sentencing memorandum presented on May 8 in the U.S. District Court for the Northern District of Illinois, U.S. Attorney Andrew Boutros summarized Cortes Cuan's immigration history.
"Cortes Cuan, a citizen of Mexico, has a history of five prior deportations from the United States," said this memorandum. "Notably, each deportation occurred after Cortes Cuan sustained criminal convictions while unlawfully present here."
At the end of 2009, "Cortes Cuan stole a jacket and sweatshirt from an individual victim," said the memorandum. "About a month later, on January 10, 2010, Cortes Cuan stole multiple pairs of jeans, shirts, and a sweater from a second individual victim. ... Then, on January 27, 2010, Cortes Cuan committed the offense of escape while in the custody of Harris County officials."
"On February 2, 2010, Cortes Cuan was convicted of the escape and theft offenses and sentenced to 90 days of imprisonment, to be served concurrently," said the memorandum. "Defendants criminal convictions came to the attention of immigration officials, and, on March 31, 2010, ICE deported defendant after he served his sentences."
Then he came back -- across Obama's border.
"Sometime after his March 31, 2010, deportation, Cortes Cuan illegally reentered the United States," said the U.S. attorney's memorandum. "On July 26, 2010, Cortes was arrested in Houston, Texas for misdemeanor criminal trespass to property or a building, and he was later sentenced to 20 days imprisonment."
"On August 5, 2010, Cortes Cuan was deported from the United States a second time," it said.
Then he came back again.
"On January 13, 2011, Cortes Cuan was convicted of a felony theft offense (upgraded in severity due to his prior theft convictions), and misdemeanor evading arrest, and was sentenced to 90 days and 35 days of imprisonment, respectively," said the memorandum.
He was deported again on Feb. 9, 2011 -- and came back again.
"Sometime after his February 9, 2011 deportation, Cortes Cuan illegally reentered the United States," said the memorandum. "On August 4, 2011, defendant was arrested in Chicago for misdemeanor retail theft and two counts of theft of lost or mislaid property."
"On September 29, 2011," said the memorandum, "Cortes Cuan was convicted of retail theft and sentenced to 6 months of court supervision."
But then he was arrested, convicted and deported again.
"On August 23, 2013, Cortes Cuan was arrested in Chicago for possessing burglary tools and misdemeanor retail theft," said the memorandum. "On September 27, 2013, he was convicted of possessing the burglary tools and sentenced to approximately one day of time served. ... On approximately March 11, 2014, Cortes Cuan was deported from the United States for a fourth time."
But that was not the last time.
"On August 8, 2014, Cortes was arrested in Chicago for aggravated assault in operating a motor vehicle, criminal damage to property, aggravated DUI, and criminal damage to property," said the memorandum.
"Cortes Cuan's conduct was a serious risk to public safety, and an officer discharged his gun after Cortes Cuan almost struck the officer with his vehicle," said the memorandum. "On April 7, 2015, Cortes Cuan was convicted of aggravated assault and aggravated DUI and sentenced to 24 months probation."
"After receiving a second-chance sentence of probation on June 11, 2015, Cortes Cuan was arrested for misdemeanor battery in Norridge, Illinois," said the memorandum. "On August 25, 2015, Cortes Cuan was deported from the United States for the fifth time before completion of his battery case. ... Because of the intervening deportation, Cortes Cuan was subsequently convicted of this offense on June 26, 2025 and sentenced to eight days imprisonment."
And he came back again.
"Sometime after his August 15, 2015 deportation," said the memorandum, "Cortes Cuan illegally reentered the United States."
As noted in a June 8 press release from the office of the U.S. Attorney for the Northern District of Illinois, Cortes Cuan has now been sentenced to prison for unlawfully reentering the United States.
"Cortes Cuan was previously deported from the United States on five occasions," said the release. "Cortes Cuan, 38, pleaded guilty in April 2026 to one count of unlawful re-entry after removal. On June 3, 2026, U.S. District Judge LaShonda A. Hunt sentenced Cortes Cuan to 14 months in federal prison. The conviction subjects Cortes Cuan to removal from the United States."
And it is no longer Obama's border he would encounter if he tried to cross it.