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Statement 1:
"He would be willing to sign something assessing the liquidated damages of $100,000 to misfit boxing in the event he withdraws."
Statement 2:
"He will be willing to sign something assessing the liquidated damages of $100,000 to misfit boxing in the event he withdraws."
Yes, in this case "would" carries some connotation of uncertainty. Statement 2 makes a positive statement, indicating that something "will" happen, while statement 1 uses the modal verb "would", which is often used in the apodosis of an if-then sentence. Therefore, even though both statements include the same condition ("in the event he withdraws"), the first places more emphasis on the conditionality.
Note that "would" can also make a sentence more polite. Thus, if the boxer's agent were negotiating, he or she could use statement 1 as a slightly more polite version of statement 2.
While such a use of 'would" can indicate a degree of uncertainty, it may merely be used to indicate something that hasn't,use happened, and might not happen, but is quite probable. A statement such as:
He would be willing to sign {document X} if he were asked to
Implies no uncertainty, merely that the condition has not yet arisen. In the example statement, a similar condition, not yet fulfilled, may well be implied.
