Vote + wall-of-text
This fight is hard to predict because EVERYTHING that Les does is conditional. EVERYTHING. Even his blade is based on a probability of guessing the opponents weight correctly.
This kind of character is difficult to judge in non-interactive tournaments. I think the character is very fascinating, but /u/TheSpectatr, I hope your next character (for the next tournament) is more suited to theorycrafting. I really like your powers and design, so I really do hope you also join the next tournament.
ANYWAY. I haven't made up my mind yet.
I will assume that Les either guesses the weight right or that DWAT doesn't respond (thinking that if he answers, it is a trick).
SO, at the beginning, Les gets his 1 foot knife (I would NOT call that a sword, haha).
I will start by saying that Les has to fight somewhat defensively, given the nature of Dwat's tools.
MATH TIME:
Probability of X happening = P(X)
KEY PROBABILITIES:
P(a level 2-4 ability) = P(operation) * P(Level 2-4) = 0.5 * 0.75 = 0.375 = 37.5%.........(so 37.5% of getting a speed increase, 37.5% chance of getting a shield or better with subtraction)
P(2 level 1 rolls) if two abilities are activated = (1-P(a level 2-4 ability))2 = 40% (meaning that 60% of the time, Les will have at least )
P(subtracting shackles) = P(Sub) * P(Level 4) = 0.5 * 0.25 = 12.5%
DUE TO GROPING BLADE being Dwat's obvious best option, this match will CERTAINLY devolve into a knife-fight.
NOW IT"S TIME TO LOOK AT LES'S ABILITIES that can help or hinder in a knife-fight
therefore, Level 1 does nothing to help Les; and Levels 2-4 sort of help equally. The shorter cooldown helps for obvious reasons. Addition is NOT Les's best hope this match
MATH BREAK:
Level 2-4 of addition help only with speed. Level 1-4 of subtraction increasingly reduce Dwat's effectiveness at fighting. Les will PRAY for subtraction.
P(L4 Subtraction) = 0.25 * 0.25 = 0.0625 = 6.25%..........P(NOT GETTING L4 Sub with two active powers = (1-0.0625)2 = 87.9%...so Les CANNOT rely on getting the shackles.
Les will NOT get the shackles almost 9 times out of 10
SO. It is my opinion that Les will lose the knife fight. Meaning that Les will probably end up blinded. Meaning that Les loses this match.
The case is a nonfactor. Once Les is blind, Les loses.