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Dr. Winsmann is a Harvard Medical School affiliated, licensed psychologist in the Commonwealth of Massachusetts and in the State of New York. He maintains a private practice, and he has completed more than 300 forensic evaluations, having been retained by attorneys and appointed by Courts to conduct forensic evaluations. He has worked on cases in numerous jurisdictions including Massachusetts, New York, New Hampshire, Washington State, California, Florida, and in federal courts. Dr. Winsmann has testified as a retained and a Court-appointed expert witness in both state and federal courts. Dr. Winsmann is valued for his ability to apply psychological concepts to legal matters along with his speaking abilities. Dr. Winsmann is the President of the Association for Scientific Advancement in Psychological Injury and Law. Additionally, Dr. Winsmann has extensive experience in providing psychotherapy to individuals, couples, and families.

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Dr. Winsmann completed a fellowship in psychoanalytic psychotherapy at the Massachusetts General Hospital Center for Psychoanalytic Studies as a Harvard Medical School Clinical Fellow, where he subsequently served as a Faculty Member. Dr. Winsmann serves at the Moderator of PsyLaw, which is an international email list comprised of approximately 1000 members involved in forensic psychology.

Dr. Winsmann served as a Captain in the United States Air Force Reserve, where he completed and supervised the completion of character evaluations on those desirous to become officers in the military.