Donald Trump vs Wilson Fisk/Kingpin [MCU Daredevil]
Donald Trump has had a couple of days as president, and he's bored. All the world leaders are giving him grief, Biden seems to be hiding in the White House playing pranks on him, and worst of all his new aides and advisors insist on proof-reading his tweets for "offensive content" before he can post! Sad!
He decides he's bailing out early. He's convinced his right hand man Pence to resign with him, and instead they're going to go try to win the mayor's office of Trump's home city, New York City. Much lower key, closer to his apartment and less scrutiny for his tweets. Meanwhile in Hell's Kitchen, Wilson Fisk is deciding that his master plan requires major political favour in order to progress, and as such he will run for mayor of New York. Fisk has made public appearances on TV prior, but is not known to be the Kingpin yet. Trump has the renown of being president, but also the infamy of bailing on the position quickly.
Round One: Straight up mayoral election campaign. Both may use what they have at their disposal, albeit Fisk is seen as more upstanding and trustworthy and thus faces less scrutiny. Trump is not in most people's good books, and will face more apparent scrutiny. If Daredevil catches on to illegal actions of either candidate (say money laundering from Fisk, or Trump bribing Russian hackers to aid his campaign) he will find them, beat them, and hand them over with incriminating evidence to the authorities. If Punisher catches on that either is conducting more serious crimes (drug trade, human trafficking, paying for assassinations or "hits") then he will successfully kill them. Who becomes mayor?
Round Two: Turns out Steve Rogers (Captain America himself) has run for mayor of New York, and wins in a landslide. Trump and Fisk go back to their enterprises. Coming to blows over a land permit that Fisk needs specifically for the Japanese but Trump needs for his Trump Tower 2, the two propose a friendly wager. Whoever can make the most money over a two month period, gets the rights to the land. Nelson and Murdock are overseeing the challenge, ensuring that the participants adhere to the strict rules. Personal wealth cannot be added to the "money made" total, and neither can "small loans" or "investments" from other parties for the sake of winning the bet (so Nobu can't hand Fisk a cool 30 mil to guarantee he gets the land). Fisk can make the money illegally, but has to launder it carefully. Trump can also try making money illegally, but will risk the ire of the gangs and other factions if he encroaches on their turf. Neither can target the other, and must aim to win and not make the other lose. Who makes the most money?
Round Three: All out war. The challenge prior was a wash due to Daredevil finding Fisk dealing with the Japanese on the side, and Trump attempting to get the Russians to swing the challenge for him. Both have decided to take the block by force, rallying what allies they have to try and claim the block and occupy it until the other side is eliminated. Fisk has his entire criminal empire from Daredevil Season One (so the aid of the Russians, the Chinese, Japanese, his hired guns, the services of Leyland and Wesley and anyone else he can afford). Trump has a small cadre of Secret Service agents he "acquired" from his few days as president, as well as his personal bodyguard detail, any private security/mercenary groups he can afford, and the aid of the Russian Government (who are only willing to act covertly, and are unwilling to go public with their support). Both sides are vehemently against drawing public attention to the war, and insist on carrying out the conflict behind the scenes. The NYPD and Daredevil will be allowed to intervene, but have to work out what is going on beyond typical gang violence. Who wins?
Bonus: Realising a war would be terrible for business, both sides agree a peace treaty. Donald can build Trump Tower on the block, but Fisk gets to give the basement and everything beneath it to the Japanese. Both realise the other is too influential and untrustworthy to let live, and begin plotting to kill the other at their next one-to-one meeting, a month from that point. Trump can use his finances to seek the best hand to hand/exercise coaches that money can buy, and whereas Fisk will be spending the month plotting to ensure Trump's guards will be killed during their meeting, and the subsequent takeover of Trump's assets runs smoothly in the wake of Donald's death (if it occurs). Due to security checking the duo for weapons, no weapons of any sort will be permitted in the boardroom they meet in. It will be a straightforward unarmed fight to the death. Who comes out on top?
TL;DR Round One: Fisk (not outed as a baddie) and Trump (bailed out of presidency) run for mayor, who wins?
Round Two: Fisk and Trump have a money making competition over the span of two months. Both can make money illegally so long as they launder it covertly and aren't caught in illegal acts by Daredevil or Punisher. Who makes the most?
Round Three: War. Fisk gets the backing of all his criminal associates and lackeys; Trump gets a squad of Secret Service guys, whomever he can hire, and the Russian Government (who wants to keep their involvement on the DL). Who manages to kill the other?
Bonus Round: Unarmed combat. No backup, no weapons of any sort, unarmed fight to the death in a boardroom. Trump gets a month to train and prep, Fisk spends the month planning a takeover of Donald's company after he (presumably) kills Trump. Who wins?