"Every new president comes in with the Saudis with high expectations and then in some cases they're disappointed," Robert Jordan, who served under the George W. Bush administration, said on "Squawk Box," ahead of Trump's international trip.
"The George W. Bush administration I think came in with high expectations, but we didn't get very far with the Israeli-Palestinian peace process. Likewise with Obama," he said.
"I think we've got to keep our expectations in check," Jordan added.
Saudi Arabia is the first location on the president's five-stop tour across the Middle East and Europe. The country is making several efforts to impress Trump on his trip and further cement its spot as a major player on the world stage. The effort marks a stark change from the strained U.S.-Saudi relationship under the Obama administration.
Also in contrast to the Obama White House, the Trump administration appears to be moving toward a more traditional U.S. approach of favoring Saudi Arabia over its regional and religious nemesis Iran.
Jon Finer, former chief of staff for Secretary of State John Kerry, said Washington will be watching to see if Trump can change the subject from the Russia investigation and the internal management of the White House.
"The big substantive area I think (is) going to be counterterrorism," Finer said on "Squawk Box." "He will work with the Israelis and Saudis to see if we can build close relationships on counterterrorism. And then secondly, Iran."
Finer, who also served as director of policy planning under Kerry, said Trump's stop in Saudi Arabia is almost guaranteed to get a positive reception. "These countries are excited about some of the new approaches that Trump is adopting, particularly his aggressive stance on counterterrorism and Iran," he said.