"When did we beat China in trade? When did we beat Japan in trade? When do we beat ISIS? Do you ever hear a good story?" Trump said, addressing a packed Iowa gymnasium.
"We don't win. We don't win ever. When was the last time we had a victory? We don't have victories anymore. We lose on trade, we lose on health care -- Obamacare is a disaster -- we lose on every single aspect of our life with these politicians," he said.
Delivering his second-shortest speech of the campaign, Trump -- in stark contrast to what is expected to be an optimistic address from the President -- trashed the Obama administration's handling of the Syrian refugee crisis and predicted homegrown terrorism would continue to be a growing threat under current leadership.
"We're like the stupid sucker, and we're not going to pay anymore for all this stuff anymore. Anybody who comes in, if I win, they're going back out," he said of the the costs the U.S. has picked up due to the refugee crisis.
The Republican presidential front-runner's speech unfolded as excerpts of the GOP State of the Union response made clear the party is aiming to project a more inclusive tone before a national audience.
Republican Gov. Nikki Haley of South Carolina, in an excerpt of her rebuttal to Obama, urged voters to "resist that temptation" of following "the angriest voices."
"During anxious times, it can be tempting to follow the siren call of the angriest voices," Haley will say. "We must resist that temptation. No one who is willing to work hard, abide by our laws, and love our traditions should ever feel unwelcome in this country."
The national GOP is sending a clear signal by tapping Haley, who was praised for her response to the controversy over the Confederate flag in Charleston last summer, as the ambassador of their party on the big stage.
Though perhaps meant to be an antidote to the flame-waving Trump, the GOP front-runner showed no signs of changing his own tone on Tuesday.
He once again cautioned against allowing refugees from the Syrian civil war to come into the United States, warning that those refugees could be a "Trojan horse."
Trump even dismissed improving unemployment numbers, calling those figures a scam for not counting individuals who have stopped looking for work as unemployed.
But Trump hinted Tuesday that he will take little stock in Obama's words later Tuesday night, first joking that he "won't be watching the speech," before saying,"Nah, I probably will."
"You gotta watch, you gotta watch," Trump said. "See what the hell's going on. Because he (Obama) doesn't know, so someone has to."
Trump also offered a starkly different message on guns than the one Obama is expected to deliver Tuesday night, a week after announcing executive orders that would expand background checks.
The Republican front-runner, who makes a point of highlighting his strong pro-Second Amendment views at every campaign stop, once again slammed gun-free zones, whose existence on military bases and schools Trump pledged to end in a separate speech just days earlier.
"That's like candy. That's like I want a piece of apple pie," Trump said of how "sickos" view those gun-free areas.
Beyond lamenting the woes of the country, Trump also dedicated some of his 38-minute speech to hitting his political foes: notably Texas Sen. Ted Cruz, who has overtaken Trump's first place position in Iowa in several polls.
Trump again raised the issue of Trump's Canadian birthplace and suggested Cruz does not meet the requirement that the U.S. president be a "natural-born citizen."
The brash billionaire went further, though, also slamming Cruz's support for phasing out the ethanol subsidies that Iowa's agricultural economy relies on.
"By the way, Ted is totally against ethanol, please remember that," Trump urged the crowd. "And I'm for ethanol."
Trump also slammed the top two Democratic candidates for president, suggesting Sen. Bernie Sanders -- a Democratic socialist -- is a communist and asserting that former Secretary of State Hillary Clinton should be in prison.
"She probably should be in prison, in all fairness," Trump said, echoing a message many of his supporters have carried to his rallies in the form of chants and printed T-shirts.