In this paper it is shown that in order for the trimmed mean to be asymptotically normal, it is necessary and sufficient that the sample be trimmed at sample percentiles such that the corresponding population percentiles are uniquely defined. (The sufficiency of this condition is well known.) In addition, the (non-normal) limiting distribution of the trimmed mean when this condition is not satisfied is derived, and it is shown that in some situations the use of the trimmed mean may lead to severely biased inferences. Some possible remedies are briefly discussed, including the use of "smoothly" trimmed means.
"The Asymptotic Distribution of the Trimmed Mean." Ann. Statist. 1 (3) 472 - 477, May, 1973. https://doi.org/10.1214/aos/1176342412