One wonders whether American Airlines used an outside contractor to develop the scheduling software that is allowing too many pilots to take vacation over the holiday season. If so, then both that contractor and American are probably taking a careful look at the limitation-of-liability provision(s) in the contract and/or in the statement of work. See Oops: American Airlines Accidentally Let Too Many Pilots Take Off The Holidays, NPR.org, Nov. 29, 2017. (See also the risk-by-risk post linked below.)
UPDATE: CNN is reporting that the cost to American Airlines could be in the range of $10 million, according to a JPMorgan estimate.