Greta: We Deserve to Know Why Obama Isn't Attending Scalia's Funeral

Nikki Haley: Why I'm Endorsing Marco Rubio

ABC News reported that President Obama plans to visit Cuba sometime next month. It would be the first presidential visit to the island nation since Calvin Coolidge visited it in 1928.

On The Kelly File, Jeb Bush called news of the visit tragic.

"When you have a different view than the Castro regime, you're put in prison," the former Florida governor said. "It breaks my heart."

Bush said that opening diplomatic relations with Cuba "legitimizes" the Castro regime in the same way that negotiating a nuclear deal with Iran legitimized the regime there, without any concessions on their part.

"My hope is that Cuba will be free one day, and that's when the president should be going there. Not at a time when there's no efforts to free the country for its people."

Watch the full interview above.

George W. Bush Warns 'the Lessons of 9/11 Are Being Forgotten'

'These Campaigns Need to Be Tough, Because the Job's Tough': Bush 43 Talks 2016

'O'Reilly Factor' Guests Clash Over Trump's National Security Credentials

Krauthammer: If GOP Field Fails to Consolidate, Trump Will Win Nomination