“How many years of files is enough, and how many years is too many?”

[EDRM Editor’s Note: The opinions and positions are those of Michael Berman.]

“How many years of files is enough, and how many years is too many?”

That was one question in Flores v. Guevara, 2025 WL 790795 (N.D. Ill. Mar. 12, 2025).

Plaintiff filed a motion to compel in a Monell case involving the City of Chicago. This was one of a series of cases involving Reynaldo Guevara. 

Guevara was formerly a Chicago police detective.  Cruz v. Guevara, 2024 WL 4871369, at *1 (N.D. Ill. Nov. 22, 2024). The Chicago Tribune reported that:

The Cook County Board’s Finance Committee approved $24.1 million in settlements related to interrogations and subsequent prosecutions tied to disgraced Chicago police Detective Reynaldo Guevara yesterday, paving the way for approval by the full board today.

In all, the National Registry of Exonerations at the University of Michigan tallied more than 40 individuals who were wrongly convicted based on Guevara, partner Ernest Halvorsen, or other detectives’ misconduct — including coerced false confessions or witness identifications — through threats or violence.

That misconduct has been costly for city taxpayers already: cases that named Guevara cost $39.3 million in 2019, 2020 and 2021 alone, not including the cost to pay outside counsel to defend the city in court.

Daywatch: Cook County commissioners advance $24.1 million in settlements – Chicago Tribune (Oct. 24, 2024).

Cook County will pay $24.8M to victims of disgraced Chicago Police Department Detective Reynaldo Guevara – ABC7 Chicago (Oct. 23, 2024)(eight men, convicted of serious crimes and later exonerated will each receive $3.1 million: “The men still have lawsuits pending against the City of Chicago.”).

The Chicago Sun Times reports that 50th murder case connected to disgraced former Chicago police detective is overturned by judge – Chicago Sun-Times (Mar. 4, 2025).

THE MEET & CONFER HURDLE IN FLORES

Before reaching the question in the title – – how many years was enough – – there was a procedural hurdle.  The Local Rules required a pre-filing “meet and confer.”  The court wrote:

The plaintiff says only that “[t]he parties have conferred many times over the phone and in writing; have reached impasse ….” The court realizes that the plaintiff’s law firm is not particularly fond of the certification requirement, see e.g., Ezell v. City of Chicago, No. 18 C 1049, 2022 WL 3081829, at *1 n.2 (N.D. Ill. Aug. 3, 2022); Ezell v. City of Chicago, No. 18 C 1049, 2021 WL 2136395, at *2 (N.D. Ill. May 26, 2021), but attorneys should not be so dismissive of Local Rules. They may appear futile to some lawyers, and probably are in this case, but they are Rules, after all.

Flores v. Guevara, 2025 WL 790795 (N.D. Ill. Mar. 12, 2025).

The parties had exchanged emails; however, the court wrote that emails “don’t count under Local Rule 37.2….”  The court added:

Discovery tends to get confusing, sometimes irretrievably so, because attorneys often choose to make it that way as a strategy and refuse to take a reasonable view of what they actually need in discovery on one side and what they really should provide in discovery on the other side. That may or may not have been the case here.

But, when things get that bad, that’s the time to actually meet and confer, as Local Rule 37.2 mandates, and do so in good faith. [Emphasis in original].

Id.

The court inferred that there had been only one phone call and:

[F]rom an objective perspective, one has to question how important the discovery at issue is to the plaintiff’s case, as well as whether the defendant is merely stonewalling. From an objective perspective, it looks as though the attorneys went through the motions, drew lines in the sand, and just decided to file well over one thousand pages of briefs and exhibits …  over the course of about a month and let the court “unravel it all now.”  If a dispute is that extensive, it would seem to merit more than a single phone call five months ago…. But here we are. [citations omitted].

Id.

The Flores court wrote that it was a “shame” that given “all of these similar cases,” the parties had not arrived at “a single, agreed-upon protocol to resolve these recurring issues….”

The court then made a point that I have written on before.  A litigant may be “right” and still lose.  See There’s No Right or Wrong Answer – But There Are Mistakes (Apr. 19, 2024); Court Holds That an ESI Protocol Must be Specific in GenAI Copyright Class Action – EDRM (Mar. 27, 2025).

The Flores court wrote that given the broad discretion courts have over discovery disputes and the number of cases involving the same defendant that are assigned to different Judges, it “means two or three or four different judges could arrive at different resolutions of very similar disputes and none of them would be ‘wrong.’… Indeed, that substantial discretion almost ensures inconsistency.”

The Flores court proceeded to rule, apparently deeming the “meet and confer” requirement met.  The court addressed an issue of discovery of open homicide files that is not covered in this blog.  It then reached the “date range” question.

HOW MANY YEARS IS ENOUGH? TOO MANY?

The Flores court held that it was not worth fighting over and there was no definitive answer.

The Flores court wrote: “The other dispute is also another all-too-familiar one in these Guevara cases and, really in litigation in general: how many years of files is enough, and how many years is too many? These are the types of disputes that ought to be resolved through good faith negotiations as Local Rule 37.2 directs. But, plaintiff’s law firm and the City’s lawyers, as already suggested, don’t have the best history with Local Rule 37.2….”

The court noted that, in another case, the parties “haven’t done much in that vein, conferring for less than an hour over their two motions in the course of a year and, seemingly, refusing to budge.”

It cited another decision: “[T]he parties have succeeded in proving (1) that the dictates and aspirations of Local Rule 37.2 are no match for them … the parties figuratively have engaged in trench warfare, refusing to budge more often than not, lobbing shells at one another in the form of discovery motions and associated filings which span over 2,250 pages of discovery dispute filings.”

And, in another related case “the plaintiff’s offer of ‘dep-for-dep’ was an excellent, time-saving and judicial resource-saving compromise…. But, unfortunately, it was one the defendants rejected out-of-hand; ….”

In Flores, the instant case: “The plaintiff’s lawyers already have, or are getting, files for a three-year period: 1987-1989. They want two more years’ worth, from 1985-1986.” 

Extrapolating from defense data, the court wrote:

So, we are arguing over three years and 400 files versus five years and perhaps 666 files, assuming an average of 133 files per year. Neither side, however, provides any support for their steadfast positions. Why, for example, are 400 files not enough to prove a Monell claim? Plaintiff offers no examples of cases that were lost because a plaintiff had no more than 400 files. Why, for another example, is the defendant sure that 400 is adequate? The defendant provides no examples of cases the defendant lost in which there were 400 files or fewer. For that matter, why does the burden of production outweigh the probative value of the files at the 401 mark and not at the 667 mark? Again, the defendant provides no useful analysis. Neither side does.

Id.

The Flores court noted that no statistical evidence had been presented and also wrote:

One supposes that a statistical expert could study the matter and offer an opinion that 400 files was too small a sample size. Of course, one also supposes that a statistical expert could study the matter and offer an opinion that 400 files was a more than adequate sample size. What the expert said would, of course, depend on which side engaged the expert, so their opinions would provide little real guidance for the resolution of this dispute…. But, if we had mini-trials over these types of discovery disputes, litigation would simply never end and the only people who might be happy would be attorneys.

Id.

The court then wrote:

The fact of the matter is, as surely the parties’ teams of attorneys must realize, there is no definitive answer. Three years or five. Six-hundred-sixty-six files or four hundred files. This is where being reasonable and compromising in good faith comes in. It’s not worth fighting over and it’s not worth further expenditure of judicial resources, especially over several cases. As there is no definitive answer and neither side has argued convincingly for one, and they have been incapable of agreeing to one, the defendant shall produce four years’ worth of files, from 1986-1989. [Emphasis added].

Id.

I am reminded of a book by Joseph C. Goulden, “The Benchwarmers: The Private World of Powerful Federal Judges” (Weybright and Talley 1974).  Two attorneys met the trial judge in Chambers on the morning of trial.  The Judge asked if they had tried to settle.  The lawyers responded that they had.  The Judge asked how far apart they were.  In the 1970’s, they responded “$2,000.”  The Judge put on his hat and coat, walked past his secretary, said “mark this case settled,” and walked out. 

In a prior discovery decision, the Flores court wrote:

One more note. Some stridency from the plaintiff and a little indignation from the defendants are seeping through, at least a little, in their discovery submissions. Unfortunately, that is par for the course. One’s clients might be “good guys” and they might be “bad guys,” but there is no need for stridency in discovery briefs or Rule 37.2 conferences. If you want to pontificate a bit on the quality of your case, do it in a substantive motion before Judge Tharp or save it for trial, where it might count. It is ineffective and inappropriate here. Counsel might wish to turn the temperature down a bit. It is precisely that which is manifested by this case that has caused judges to be so critical of the discovery process.

Flores v. Guevara, 2024 WL 4203080, at *4 (N.D. Ill. Sept. 16, 2024).

I have written several blogs citing cases that suggest compromise and cooperation.  Courts have repeatedly said that a party may be “right,” but still lose.^[1]

Notes

[1] See There’s No Right or Wrong Answer – But There Are Mistakes (Apr. 19, 2024); Court Holds That an ESI Protocol Must be Specific in GenAI Copyright Class Action – EDRM (Mar. 27, 2025).

Assisted by GAI and LLM Technologies per EDRM GAI and LLM Policy.