There was a time when Donald Trump was all the rage on the campaign trail, drawing record crowds as enthusiastic supporters cheered the political outsider. Fast forward to present day and Trump is in the headlines for all the wrong reasons, reaching a new low with less than 40 days until Election Day.

Trump's low blow

When Trump finally met one-on-one with Hillary Clinton during last Monday night's debate, he looked on in awe when the former Secretary of State brought up an uncomfortable point in his history. Trump was one of the leading voices of the Miss Universe pageant, but after Alicia Machado was crowned the winner, she gained nearly 60 pounds in the following months.

Trump was not happy about the weight gain, and forced Machado to be filmed during public work outs. After Clinton brought the fat shaming up during the debate, the billionaire real estate mogul has gone on the attack, going as far as accusing Machado of taking part in a sex tape. This issue was highlighted during the September 30 edition of "Morning Joe" on MSNBC.

Panel guest Eugene Robinson described Trumps' latest attack as "flailing" in response to the fact that "He can't deal with the fact that he got creamed in that debate." "He did a tweet-storm early this morning, which is fascinating," host Joe Scarborough said, as the panel couldn't hold back their laughter.

"Does this mean he now knows he lost the debate?" Scarborough wondered. The panel were left in disbelief that Trump would even mention the alleged sex tape, which Snopes concluded doesn't exist in the first place.

On the issue of Trump's previous comments about women and their weight, co-host Mika Brzesinski did not hold back.

"That is what he is telling women, that there is a line of what is beautiful," Bzezinski said, noting, "That he and other man, who are quite rotund, determine, OK?" Brzezinski went on to describe the situation, stating, "It's so sick. It's beyond personal."

Trump's rough week

In addition to his public fat-shaming feud with Machado, the former host of "The Apprentice" has been hit with the release of two separate bombshell news investigations.

Earlier this week, "Newsweek" uncovered that Trump had violated the Cuban embargo when one of his companies spent nearly $70,000 in the country in the late 1980s during the leadership of Fidel Castro. In addition, The Washington Post broke a story late Thursday night, which found that the Donald J. Trump Foundation was not properly certified as a charity in New York, resulting in illegally solicitations from public donors. While Trump is only within three points of Clinton on a national level, all eyes will be on the next round of polling that will reflect the negative week in question.