Grover Cleveland, also known as the Walrus President, is one of the more interesting competitors. Out of the 44 Presidents, he was two of them. That's not a fat joke; he actually left office after his first term, only to return four years later. In combat terms, he knows when to lay low, choosing to strike when the time is right. A thoughtful opponent is a dangerous opponent.
Wilson, however, was no pushover. His successful re-election can mostly be attributed to his use of the slogan, "He kept us out of war." Mere months after winning the election, Wilson declared war on Germany. He really liked conflict. He even refused to listen to his doctors when they cautioned him from going on a national tour. A tour that, coincidentally, caused him to have a stroke that nearly killed him. He clearly doesn't know his own limitations. Upper hand: Cleveland.
Cleveland was also known for his deep seated hatred of "clever" names, like his opponent during his first run at President, James Blaine of Maine. Woodrow is a weird name to begin with, but his last name also started with a W, too, to which Cleveland would most likely respond, "Fuck your alliteration, Wilson."
Winner:

Match #4: George H. W. Bush vs. Rutherford B. Hayes
Both Bush and Hayes have only served one term each, leaving each on fairly even grou— JESUS CHRIST LOOK AT HAYES. Wow. We elected this guy? I wasn't aware there was a Homeless Professor Party. Who the hell supported his run for office, the Advocates for People With Crumbs in Their Beards? Was this guy a joke option on the ballot or something? How did we ever elect a stoner librarian? Good lord. No way this guy could ever spar against another man. Especially if they were sober.
Plus, Bush has more initials in his name.
Winner:

Match #5: Calvin Coolidge vs. Harry Truman
Truman was a tiny little nerd. Coolidge would stomp him and then hit on his wife.
Winner:

Match #6: Lyndon B. Johnson vs. Theodore Roosevelt
Now this is a match! On one side, Lyndon B. Johnson, the kinda guy that would take off his belt and smack the shit outta you with it if you even looked at him funny, against Theodore "Teddy" Roosevelt, a guy who was nicknamed after a god damn bear! Both of these guys are men's men. LBJ could make grown men burst into tears by simply furrowing his brow and staring at them through squinted eyes. And Teddy had an awesome moustache.
In a fair fight, each of these men would be able to hold their own, resulting in what we can only imagine to be one of the greatest match-ups of the entire tournament. Sadly, it isn't exactly fair. LBJ, of course, first stepped into the white house as Kennedy's Vice President. He didn't become President until Jacki-O was sprayed with JFK's brain-guts.
Due to this late start, LBJ only spent a total of six years in office, meaning Roosevelt has a full two minutes of free reign beating time. Now, LBJ won't bow out that quickly; he'd take the two minutes in stride and still put up quite a fight, but LBJ's loss would be inevitable with a head start like that.
Winner:




































