Trump like a heavily shorted momentum stock—this pro says beware of the squeeze

While conventional wisdom on Wall Street sees Democratic presidential front-runner Hillary Clinton beating Republican Donald Trump this fall, don't discount the billionaire's ability to surprise, said Jason Trennert, chief investment strategist at Strategas Research Partners.

In August 2015, Trennert put out a research note arguing Trump could win the White House. He wrote at the time: "If Donald Trump were a stock ... it would be hitting new highs despite a series, maybe even as a result, of analyst downgrades and downward earnings revisions." Keep in mind, Trump only officially announced his candidacy in June 2015.

"He was underowned, like a momentum stock that people kept shorting. I still believe that," Trennert told CNBC's "Squawk Box" on Wednesday, adding there's six months of campaigning left before the November election. "It's an eternity in a 24-hour news cycle."

Trump became the likely GOP nominee, after rival Texas Sen. Ted Cruz dropped out of the race Tuesday night, as the billionaire businessman emerged victorious in Indiana's presidential primary.

Clinton ended up losing in Indiana to Democratic rival Vermont Sen. Bernie Sanders, despite being ahead in recent statewide polls. However, the former secretary of state still holds a wide lead in the delegate count.

"The conventional wisdom is that the status quo is better for the market," Trennert contended, saying Clinton would certainly be considered status quo after eight years of President Barack Obama.

But Trennert said, "Organic growth would probably be better under Donald Trump than it would be under Hillary Clinton, mainly because there would probably be a focus on lower regulations and lower corporate taxes." He sees those as offsets to Trump's anti-free trade, protectionist rhetoric.

"Whatever is best for capital formation, which goes back to productivity, is better for the market," Trennert said. "If you continue to focus on financial engineering — companies are doing that, central banks are doing that — nothing good happens."

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