Could Trump legitimately secure a second term?

Bill (Yes)

President Trump could legitimately secure a second term if he can prove that vote totals in three states (GA, PA, and AZ) are invalid by disqualifying enough illegally placed Biden votes and/or factoring in legally cast Trump votes not initially counted. Trump needs a total of 270 electoral votes to win a second term—he will have 279 if he can flip the three states listed above.

One way Trump will try to reverse vote totals is to scrutinize mail-in ballots for deficiencies or fraud. Common problems resulting in tossed ballots include signatures that don't match the ones on file, ballots received after state-imposed deadlines, discovering a voter also voted in person, ballots missing a witness signature, irregularities with ballot-related materials, etc. Likewise, reviewing local voter rolls can reveal additional wrongdoing, such as votes cast by dead people, duplicate votes, etc.

If Trump can prove ballots were improperly harvested or tampered with, he may be able to get those votes disqualified. Additionally, suppose he can show there was a coordinated effort by poll workers to 'rig' the election by disqualifying or destroying legitimate Trump ballots and/or 'creating' or 'curing' ballots for Biden. In that case, he may be able to reverse vote totals.

Finally, Trump may be able to show that software programs installed to tally votes were manipulated to generate incorrect totals favoring Biden. The 2000 Presidential election wasn't decided until December 13th—after the Supreme Court intervened, and Al Gore conceded. Trump still has a legitimate path to a second term, but he will need to provide evidence to support his case.

Tyler (No)

Despite the President's recent misguided claims, it is highly unlikely he will end up winning his reelection. By exhibiting skepticism about the results, Trump is doing anything but promoting a peaceful transfer of power. In states where Trump is demanding recounts, he lost by margins of up to 100,000 votes. It is highly unlikely for that many votes to be overturned in his favor. Trump unsuccessfully called on Republican legislative leaders in Michigan to not certify Biden's 154,000 vote win in the state. While Trump has filed numerous lawsuits disputing the outcome of the election, election law expert Rick Hasen was certain the only issue that Trump may be successful in disputing had to do with counting votes that arrived after election day in Pennsylvania. However, overturning votes in Pennsylvania, experts predicted, would not ultimately impact the final outcome of the election.

There is no proof of the alleged voter fraud that Trump claims occurred. Trump's legal team asserted that the nation's computerized voting system executed an algorithm to rig the election in Biden's favor. However, the National Cybersecurity & Infrastructure Agency assured there is absolutely no proof to back these statements. He then fired the national head of cybersecurity, Christopher Krebs, after he disputed Trump's erroneous claims.

A former Trump campaign worker and Republican strategist, Karl Rowe, stated the President's efforts to flip any state from President-elect Joe Biden will be unsuccessful due to the significant margin of victory by which Biden won. Fellow Republicans like Senator Mitt Romney, Charles Dent, and Paul Mitchell also expressed their concern with the President's firm denial of the election results.