You would think the answer to this would be as easy as falling off a log, but the law makes many "nuts and bolts" things more complicated than would be expected. I haven't recently looked at the Federal Rules of Civil Procedure on calcualtion of time periods, but there is a specific rule, I think it's Rule 6, that covers this.
If the Order to which you are referring specifically says that the documents must be produced within 14 days "of the ruling", then neither the submittal date nor the signing date of that Order is what controls. Instead, as the Order would indicate, the date of the ruling itself would be controlling. If you want to post the actual Order, or email it to me, I'll be glad to look at it.
Assuming the above is accurate, my recollection of Rule 6 is that "day one" would be the next day after the ruling (the day of the event or ruling itself is virtually always excluded), and you would then count forward, including weekends and holidays, to "day 14", which is what the Rule would refer to as being the "last day". However, that "last day" must not fall on a weekend or an officially recgnized holiday (and yes, there is another Rule defining what those holidays are) --- if it does, the "last day" is considered the next day that is not a weekend or recognized holiday.
If you want to get a real kick out of how complicated something like this can be, find Rule 6 and also read what I think are referred to as the "advisory notes" at the end --- those notes give the procedural history of the Rule back through the decades. Calculation of deadlines like this causes much stress to lawyers and legal assistants since, if you are even one day late, sanctions can be imposed, or, even worse, the entire case can be subject to dismissal. I have a great story I can tell you about a similar event that happened to me a few years ago, but PM me if you want to hear it as this post has already gotten longer than I intended.
Best wishes to you and all.
