Federal agents arrested a sex offender from Milwaukee and his buddy as the two made their way to Mexico en route to join up with the Islamic State.

Thirty-five-year-old Jason Michael Ludke, who also goes by Mohammad Abdun Nassir and Abbudllah Ludke, was arrested in Tom Green County, Texas as he drove along U.S. 87 on Oct. 5 with “brother” Yosvany Padilla-Conde, a 30-year-old illegal immigrant he befriended in Milwaukee, San Angelo Live reports.

Their arrests stemmed from conversations between Ludke and an undercover FBI agent over social media that started in September, when the FBI agent received a friend request from Ludke professing his desire to make “hijra” from “darul kufr,” or migrate from the land of the infidel.

According to the Milwaukee Journal Sentinel:

During a conversation later that month, Ludke told the FBI employee he was making plans to come “there” but because he had a criminal past, he was traveling to Mexico, where he believed he could obtain a passport. In a voice chat later that day, Ludke said he lives in Milwaukee with his “brother,” converted to Islam in 2003 and he was working on his brother to join him.

The undercover FBI employee, apparently posing as a member of the Islamic State, asked Ludke to wait for further instructions before trying to leave the country so he or she could consult with a person who can help Ludke get into Raqqah, Syria, and then to Mosul, Iraq. Then Ludke uttered the Islamic creed, pledged allegiance to Islamic State’s leader and said he wanted to live under Shariah law. The next day, Ludke sent a video professing his allegiance to Islamic State leaders.

On Oct. 1, Ludke emailed the FBI employee two photos of himself and one with his “brother” who was identified as Padilla-Conde. In another video clip sent by email, Padilla-Conde pledges allegiance to the Islamic State.

The two also bragged about their martial arts and computer prowess, and claimed Padilla-Conde received weapons training while in the Cuban military, San Angleo Live reports.

The men were arrested days after leaving Milwaukee as they traveled to meet with Ludke’s Palestinian Muslim brother-in-law in Texas, where Ludke planned to marry a woman before heading to Mexico. Padilla-Conde told police he planned to ditch his partner once they crossed the border.

The two were hauled back to Wisconsin, where Ludke was wanted on an outstanding warrant and Padilla-Conde was detained because of his immigration status. Ludke told police the two left Milwaukee because they couldn’t pay their rent.

Ludke was previously convicted in 1998 of burglary and car theft charges, and again in 2002 for the sexual assault of a child, for which he was sentenced to four years in prison and four years on probation, though his probation was revoked in August 2009, the Journal Sentinel reports.

Ludke threatened to kill a federal judge in Green Bay while in Brown County Jail in 2009 and was sentenced the following spring to 32 months in prison, along with three years of probation. Ludke was still on probation from that case when he allegedly fled to join ISIS.

Court records show Ludke was born in Green Bay and was in the foster care system before dropping out of high school as a sophomore. He reportedly suffers from ADHD, bipolar disorder and depression, the news site reports.

U.S. Immigrations and Customs Enforcement issued a statement about the arrests on Friday, crediting the FBI Joint Terrorism Task Force and Tom Green County Sheriff’s officials with helping to apprehend the men.

“The United States is committed to identifying and arresting persons intent on providing material support of any kind to foreign terrorist organizations. Those organizations pose a threat to United States’ interests abroad, including threats to our military personnel, and pose a threat to the homeland upon the possible return of terrorist supporters to the United States,” U.S. Attorney General Gregory J. Haanstad said in the statement.

“Terrorism remains the FBI’s top priority in keeping Americans safe,” said Justin Tolomeo, special agent in charge of FBI Milwaukee. “The arrest of these two individuals from Wisconsin underscores how the real threat of terrorism can occur anywhere, at any time. I would like to commend the efforts of the JTTF, which includes a wide range of our law enforcement partners who work tirelessly for the safety of our citizens. We encourage all citizens to remain vigilant in reporting suspicious activity to law enforcement.”

Ludke is charged with attempting to provide material support to a terrorist organization, while Padilla-Conde is charged with aiding and abetting the same. Both men face up to 20 years in prison and a $250,000 fine, according to the ICE statement.