The Trump Administration saw its first legislative win Wednesday with the signing of the Laken Riley Act, the new law requiring all unauthorized immigrants accused of theft or violent crimes to be detained before they’ve been convicted. But not all of President Donald Trump’s efforts are on their way to swift victories.

One of Trump’s most controversial executive orders is facing major legal challenges. The president’s repeal of birthright citizenship for the children of unauthorized immigrants, a right enshrined in the 14th amendment to all born on U.S. soil, has been temporarily blocked by a judge who called it ‘blatantly unconstitutional.”

Andrew Cherkasky, a former federal prosecutor, believes this issue will go all the way to the highest court in the nation.

“It's something that the Supreme Court has not specifically spoken on in light of the idea that the parents of a child born on U.S. soil are illegal immigrants.”

Another move facing legal backlash, the administration’s federal grant freeze.

The order sparked chaos and confusion about programs like Medicaid and HeadStart. It has resulted in two lawsuits and was temporarily blocked just moments before it was set to go into effect.

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Trump’s ban on transgender service members also faces legal roadblocks. The executive order banning trans servicemember from the military is a revival of efforts Trump accomplished during his first term but was reversed by former President Joe Biden. The president's most recent attempt at this ban has resulted in a lawsuit filed by six transgender service members.

Cherkasky said these challenges are something the Trump administration prepared for.

“It's very common for presidents when they come into office to issue many new executive orders that are consistent with their viewpoints,” said Cherkasky. “You naturally get pushback on that. And one of the ways to fight against those actions of the president is to file lawsuits and then the judiciary gets to make those decisions.”

The fate of these actions, ultimately not in Trump's hands, but also not expected to end without a fight.

“He is going to vigorously fight and defend the positions that he has on these things,” said Cherkasky. “Unquestionably.”

These issues could be resolved sooner than some would think.

“The pace at which it goes through the court system can actually be quite rapid,” said Cherkasky. “Especially for sensitive cases that have immediate impacts, like the immigration issues, like the birthright citizenship issue, like certain questions regarding military orders or actions. All of those things have very high priority in the Supreme Court and can be answered in as little as 6 months to a year.”

The challenges against Tump’s birthright citizenship ban and federal grant freeze that resulted in temporary blocks are scheduled for hearings next week.