As everyone has indicated, under the Federal Rules of Evidence (Section 408), Settlement Discussions are not admissible in trial.
However, be careful, I do not think this is what you are talking about when you use the word "stipulate." A common practice in Tax Court is for the parties to submit a statement of stipulated facts to the Court. If you offered to concede certain items in exchange for a proposed deal, then it is protected under FRE 408. However, if at any time you admitted to these issues outside of settlement discussions, then that would qualify as an admission. Of course, you would still litigate that issue subject to a credibility analysis by the Judge. The Judge will potentially do more than leverage that concession, the Judge will likely tell you that while he/she does not have all the facts, it looks like the case is going to go in a certain direction. Listen carefully. If the Judge tips his/her hand in this fashion, you'd be wise to take heed.
No. Generally in any court in this country the parties cannot use statements from settlement negotiations as evidence at a trial.
This is not legal advice nor intended to create an attorney-client relationship. The information provided here is informational in nature only. This attorney may not be licensed in the jurisdiction which you have a question about so the answer could be only general in nature. Visit Steve Zelinger's website: http://www.stevenzelinger.com/
Evaluating any legal question requires a detailed knowledge of the specific facts involved. Since a short question will rarely contain all the relevant facts, the answer here should be considered a general comment for your consideration and not legal advice.
It sounds like you need a tax attorney. The Stipulation of Facts is not a basis for a hypothetical settlement. This is the items that you are saying are facts for the purposes of trial. If you say something is a fact, the court accepts it as such and deals with the remaining disputed issues. You cannot later say this is not a fact if things are not going well.
You need an attorney with Tax Court experience. You are playing a dangerous game on the eve of Tax Court.
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