WASHINGTON, DC - MAY 09:  U.S. President Donald Trump speaks during a Roosevelt Room event at the White House May 9, 2019 in Washington, DC. The Trump administration is requiring drug manufacturers to disclose the list price of any drug covered by Medicare or Medicaid with a cost of $35 or more per month.  (Photo by Alex Wong/Getty Images)
PHOTO: Alex Wong/Getty Images North America/Getty Images
WASHINGTON, DC - MAY 09: U.S. President Donald Trump speaks during a Roosevelt Room event at the White House May 9, 2019 in Washington, DC. The Trump administration is requiring drug manufacturers to disclose the list price of any drug covered by Medicare or Medicaid with a cost of $35 or more per month. (Photo by Alex Wong/Getty Images)
Now playing
02:10
Trump the deal-maker struggles on the world stage
Now playing
02:11
'Sad': Kinzinger blasts Hawley's CPAC remarks
New York Gov. Andrew Cuomo speaks during a news conference at a COVID-19 vaccination site in the Brooklyn borough of New York, Monday, Feb. 22, 2021. (AP Photo/Seth Wenig, Pool)
PHOTO: Seth Wenig/Pool/AP
New York Gov. Andrew Cuomo speaks during a news conference at a COVID-19 vaccination site in the Brooklyn borough of New York, Monday, Feb. 22, 2021. (AP Photo/Seth Wenig, Pool)
Now playing
01:12
Gov. Andrew Cuomo responds to allegations of sexual harassment
 Psaki biden White House Khashoggi Saudi Arabia sotu bash vpx _00011629.png
PHOTO: CNN
Psaki biden White House Khashoggi Saudi Arabia sotu bash vpx _00011629.png
Now playing
03:42
Bash to Psaki: Why hasn't Saudi Arabia been held accountable for murder of Khashoggi?
Speaker of the Virginia House of Delegates Eileen Filler-Corn (D-Fairfax) speaks during opening ceremonies of the 2020 Virginia General Assembly at the Virginia State Capitol on January 8, 2020 in Richmond, Virginia.
PHOTO: Zach Gibson/Getty Images
Speaker of the Virginia House of Delegates Eileen Filler-Corn (D-Fairfax) speaks during opening ceremonies of the 2020 Virginia General Assembly at the Virginia State Capitol on January 8, 2020 in Richmond, Virginia.
Now playing
04:26
Virginia's political shift from red to purple to blue
senator bill cassidy sotu bash vpx _00002611.png
senator bill cassidy sotu bash vpx _00002611.png
Now playing
01:42
GOP senator: If we continue to idolize one person, we will lose
Now playing
01:27
Kristi Noem gets standing ovation for Dr. Fauci dig at CPAC
House Speaker Nancy Pelosi
PHOTO: House TV
House Speaker Nancy Pelosi
Now playing
02:52
House passes Biden's $1.9 trillion Covid-19 relief package
covid-19 relief package house biden sot malveaux nr vpx _00000000.png
PHOTO: CNN
covid-19 relief package house biden sot malveaux nr vpx _00000000.png
Now playing
02:28
CNN's Joe Johns explains Biden's short speech as relief bill heads to Senate
Sen. Bernie Sanders AC360 intv 02262021
PHOTO: CNN via Cisco Webex
Sen. Bernie Sanders AC360 intv 02262021
Now playing
03:54
Sanders on what happens with proposed minimum wage increase now
WASHINGTON, DC - JANUARY 17: The U.S. Capitol dome is seen beyond a security fence on January 17, 2021 in Washington, DC. After last week
PHOTO: Michael M. Santiago/Getty Images
WASHINGTON, DC - JANUARY 17: The U.S. Capitol dome is seen beyond a security fence on January 17, 2021 in Washington, DC. After last week's riots at the U.S. Capitol Building, the FBI has warned of additional threats in the nation's capital and in all 50 states. According to reports, as many as 25,000 National Guard soldiers will be guarding the city as preparations are made for the inauguration of Joe Biden as the 46th U.S. President. (Photo by Michael M. Santiago/Getty Images)
Now playing
02:33
This is what's in the $1.9 trillion coronavirus package
PHOTO: CNN
Now playing
02:24
Acosta corrects CPAC organizer: Trump did lose the election
PHOTO: Pool
Now playing
01:10
Rand Paul accused of 'transphobic attack' in confirmation hearing
PHOTO: CNN
Now playing
02:39
Republicans push new restrictive election bills in 43 states
van jones minimum wage
van jones minimum wage
Now playing
02:44
Van Jones: This is a make or break issue for Democrats
US President Joe Biden speaks about the 50 million doses of the Covid-19 vaccine shot administered in the US during an event commemorating the milestone in the Eisenhower Executive Office Building in Washington, DC, February 25, 2021. (Photo by SAUL LOEB / AFP) (Photo by SAUL LOEB/AFP via Getty Images)
PHOTO: Saul Loeb/AFP/etty Images
US President Joe Biden speaks about the 50 million doses of the Covid-19 vaccine shot administered in the US during an event commemorating the milestone in the Eisenhower Executive Office Building in Washington, DC, February 25, 2021. (Photo by SAUL LOEB / AFP) (Photo by SAUL LOEB/AFP via Getty Images)
Now playing
02:28
Axelrod explains the message Biden is sending with strike
(CNN) —  

For President Donald Trump, the timing couldn’t have been worse.

Precisely as his master-negotiator credentials are being freshly tested on the global stage – and as he worries time is running short to prove his diplomatic gambles are working – the very basis for his deal-artist reputation was being dramatically undercut.

Trump was so alarmed midweek when The New York Times detailed his enormous losses as a real estate developer that he avoided cameras and reporters for an entire day – a rarity for a President ordinarily drawn like a magnet to media scrums.

As Trump increases his focus on 2020 and a potential Democratic rival, people close to him say he is intent on proving to supporters that the dealmaker they elected in 2016 is making good on his promise to bargain his way around the globe.

And though aides have insisted the President isn’t worried about who he’ll face in the 2020 election, multiple people who have spoken with Trump in recent days said he had called to discuss the Democratic race – specifically former Vice President Joe Biden – before 8 a.m., when he’s still typically in the White House residence alone with his newspapers spread out in front of him and Fox News playing in the background.

Always closely attuned to his political standing, Trump has come to view nearly all of his moves as President through the lens of his reelection effort. As he confronts a set of global crises that cast doubt on his ability to strike deals, he is openly questioning whether any of his potential rivals would fare better. And behind the scenes, he’s questioning the advice of aides as his negotiating efforts falter and his reelection nears.

“It seemed like four years would never happen. And now we’re a year and a half away, less. Think of it,” Trump said at a campaign rally in Florida on Wednesday. “It’s incredible, how time flies.”

His opponents are all over TV

In recent weeks, Trump – whose perception of an event is often shaped by the media’s coverage of it – has turned on his television expecting to see news about his administration only to find that one of the nearly two dozen people who are hoping to run against him are occupying the screen instead. At times, he has lamented that some of the Democratic candidates are getting better coverage than he did – even on Fox, his once (and usually still) reliable cheerleader.

When he did find coverage of himself this week, the headlines were dominated by foreign flashpoints that his diplomatic efforts haven’t been able to quell.

By the time Trump resumed taking questions on Thursday, the acute overseas crises that are mounting on his administration had pushed the tax revelations to the wayside. Taken together, however, the undermining of his business acumen and the uncertain state of his global negotiations amounted to a raw gut check on the most elemental of Trump’s political attributes: his ability to strike deals.

North Korea, apparently fed up with stalled talks over its nuclear program, resumed testing short-range missiles. Trade negotiations with China, once believed to be nearing a successful conclusion, were set back. A pressure campaign on Venezuela hasn’t yet yielded a transition of power. And a year after withdrawing from the Iran nuclear deal, Trump appears to be edging closer to the type of confrontation he swore against as a candidate.

So determined is Trump to strike some type of diplomatic accord that White House officials this week passed along a special phone number to the Swiss government – Iran’s emissary to the United States – in case Tehran was inspired to pick up the phone after Trump said during an impromptu news conference, “I’d like to see them call me.”

For a President already besieged by congressional oversight demands and still managing fallout from Robert Mueller’s Russia investigation, the series of challenges only contributed to an overall feeling of an embattled administration jumping between various calamities.

At the top is a President who is consumed with providing evidence to his base voters that they chose correctly in 2016 – and intently focused on the Democratic race to become his opponent.

At the rally in Florida’s Panhandle, where a subdued crowd and presidential complaints about a slippery stage gave a somewhat spiritless air, Trump claimed that one potential rival – South Bend, Indiana, Mayor Pete Buttigieg – would fall flat pitted against President Xi Jinping of China.

Trump has even complained in recent days that Biden indirectly derailed his trade talks with China, claiming that a comment from the Democratic front-runner signaled to Xi that he’d be a more pliant negotiating partner than Trump (Biden’s team says the candidate’s remark was taken out of context).

“The reason for the China pullback & attempted renegotiation of the Trade Deal is the sincere HOPE that they will be able to ‘negotiate’ with Joe Biden or one of the very weak Democrats, and thereby continue to ripoff the United States (($500 Billion a year)) for years to come,” Trump tweeted this week.

In reality, most US officials have pinned the blame for the trade talks’ breakdown on Xi, who they believe was unwilling to make the economic reforms the US has insisted on. Privately, Trump has also become frustrated that aides led him to believe a deal was closer than it actually was, believing some members of his team painted a rosier picture of the talks in an attempt to forestall an increase in tariffs.

Questioning his national security team

It’s not the only setback that’s led the President to question his team’s strategy. He publicly canceled a set of planned sanctions on North Korea in March, undercutting his team, and this week told South Korea’s President he supported Seoul in its humanitarian efforts to provide food to the North – something some advisers have opposed.

He grew irritated with his national security team this week and openly questioned their strategy in Venezuela after a planned military uprising that some US officials were counting on failed to gain steam.

Trump focused his ire on national security adviser John Bolton and Secretary of State Mike Pompeo in particular, sources told CNN.

Trump has told friends that Bolton wants to be at war in multiple places, and on Thursday the President acknowledged to reporters that he sometimes had to rein in his adviser.

“He has strong views on things but that’s OK. I actually temper John, which is pretty amazing, isn’t it?” Trump said.

He continued to air his complaints over Bolton’s handling of Venezuela in phone calls late this week.

And Trump questioned his secretary of state last week after Pompeo said during a CNN interview that the Russians had convinced Venezuelan strongman Nicolas Maduro to remain in the country – asking Pompeo what he had done to handle it.

Trump later called Putin himself.

Still, while the President has blamed his predecessors for most of his foreign policy problems – Russian interference in the election, North Korea’s nuclear capability and the “horrible one-sided” Iran nuclear deal – Venezuela is a crisis that has escalated sharply during his administration, and will reflect more on Trump than on any past president.

And perhaps more than any other foreign flashpoint, Trump has privately linked the Venezuela situation directly to his own political fortunes, particularly in Florida. Some Trump political advisers see a political upside if Maduro leaves office, believing Venezuelan American voters in Florida might be more inclined to vote for Trump and Republicans.

But that eventuality hasn’t come to pass, at least not yet. Speaking in Florida at the rally this week, Trump appeared to acknowledged the progress would be more incremental than immediate.

“How we doing in Venezuela?” he asked. “Step by step, step by step.”