UNITED STATES DISTRICT COURT

NORTHERN DISTRICT OF ILLINOIS

EASTERN DIVISION

SYLVESTER BONNER, JR., )

)

Plaintiff, ) Case. No. 12 C 981

v. )

 ) Judge John J. Tharp, Jr.

DANIEL O’TOOLE, et al., ) 

) Magistrate Judge Arlander Keys

 Defendants. )

MEMORANDUM OPINION AND ORDER

On February 12, 2010, City of Chicago Police Officers

entered the home of Sylvester Bonner, Jr., who lived at the time

at 4929 W. Adams, in the basement apartment designated unit BA.

The officers had a warrant, but – as it turned out – not for Mr.

Bonner’s unit; the warrant covered the “entire 1st floor of the

three flat building located at 4929 W. Adams.” According to Mr.

Bonner, the building at that address is not a three flat, but is

a larger residential apartment building with four floors and at

least 30 units. 

On February 12, 2012, Mr. Bonner sued the City and the

officers who entered his apartment, including Officer Daniel

O’Toole, alleging violation of his Fourth and Fourteenth

Amendment rights. He also raises a Monell claim, see Monell v.

Department of Social Services, 436 U.S. 658 (1978), alleging that

the City failed to train its officers in the use of informants

and maintains a code of silence that allows officers to obtain
warrants by using fraudulent information. He alleges that, as a

result of the defendants’ misconduct, he “sustained injuries,

humiliation, and indignities, and suffered great mental and

emotional pain and suffering all to his damage.” Complaint, ¶25. 

 According to Mr. Bonner, the warrant at issue in this case

had a number of irregularities: first, the address 4929 was

written in and initialed over the typed address, which was 4927;

second, the target of the warrant was a woman identified as “ShuShu” who, according to Mr. Bonner, lived at 4929 W. Adams but in

the 1st floor unit (designated 1B), not the basement unit. Mr.

Bonner alleges that the officers involved knew their information

was unreliable, but nonetheless sought and obtained a search

warrant, intentionally presenting false information to the judge

to obtain that warrant. Complaint, ¶¶18-20. He alleges that,

because of this, the entry and subsequent search of his home were

illegal, in violation of the Fourth Amendment. He alleges that

the defendant officers intentionally procured the search warrant

with false information and that they intentionally executed the

search warrant on the wrong apartment; he also alleges that,

during the course of their illegal search of his home, the

defendants illegally seized property belonging to him, including

a computer, a cellphone, a surround sound system and other items. 

He has also sued the City of Chicago for indemnification.

The case was initially assigned to Judge Holderman, who

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referred the case to this Court for discovery supervision;

thereafter, the case was reassigned to Judge Tharp, who left the

referral intact. Discovery proceeded, with both sides serving

written discovery and pursuing depositions of various witnesses. 

Most relevant to today’s decision, Mr. Bonner served requests

seeking information and documents relating to warrants issued in

the five years prior to the incident outlined in the complaint. 

And the City served contention interrogatories, documents

requests and requests to admit. Per the Court’s order, fact

discovery was set to close on October 31, 2012.1 

Two weeks before discovery closed, on October 17, 2012, Mr.

Bonner filed a motion to compel the defendants to respond to

certain outstanding discovery requests. Specifically, he asks

the Court to order the City to turn over all documents relating

to searches executed in the five years prior to the incident

covered in the complaint in which defendant Daniel O’Toole was,

in any way, involved. In that same motion, he also asks the

Court to strike the defendants’ requests to admit. 

Two days before the fact discovery cutoff, the defendants

followed suit with their own motions to compel. The City filed a

motion seeking an order compelling Mr. Bonner to respond to a set

of contention interrogatories and an accompanying document

1The Court has since extended the discovery cutoff to

January 31, 2013.

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request it served on Mr. Bonner on July 18, 2012. And Officer

O’Toole filed a motion seeking an order compelling Mr. Bonner to

respond to deposition questions relating to his mental health,

or, in the alternative, to bar Mr. Bonner from claiming any

damages related to his mental health status. The Court considers

each of these motions below.

Discussion

The federal discovery rules are liberal to further the

parties’ interest in preparing a case for trial or in settling

their disputes in advance of trial. See Bond v. Utreras, 585

F.3d 1061, 1075 (7th Cir. 2009); see also Kodish v. Oakbrook

Terrace Fire Prot. Dist., 235 F.R.D. 447, 450 (N.D. Ill. 2006)

(“the scope of discovery should be broad in order to aid in the

search for truth”). Pursuant to Federal Rule of Civil Procedure

26(b)(1), “[p]arties may obtain discovery regarding any

nonprivileged matter that is relevant to any party's claim or

defense . . . . Relevant information need not be admissible at

the trial if the discovery appears reasonably calculated to lead

to the discovery of admissible evidence.” Fed. R. Civ. P.

26(b)(1). “The burden rests upon the objecting party to show why

a particular discovery request is improper.” Kodish, 235 F.R.D.

at 450.

Mr. Bonner’s Motion to Compel

Mr. Bonner requested that the defendants produce documents

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relating to search warrants executed by Officer O’Toole from

January 1, 2005 through February 12, 2010. For each such

warrant, he requested the warrants themselves, plus complaints

for search warrants, search warrant data sheets, supplementary

reports, raid activity summary reports, vice case reports and

evidence recovery logs; in a subsequent request, Mr. Bonner added

to the list of requested categories of documents arrest reports,

photographs and all other reports. 

In response to Mr. Bonner’s discovery requests, the City and

Officer O’Toole identified 349 searches during the relevant time

period in which Officer O’Toole was somehow involved. Of those

349, Officer O’Toole was the affiant on just 45. The City has

offered to produce documents during this period for searches in

which Officer O’Toole was the affiant – 45 of the 349 searches. 

In fact, the City has produced more than 500 pages of documents

relating to just those 45 searches, and it claims that the time

and effort that have gone into producing documents for those 45

searches show just how burdensome responding to the full request

would be. Officer O’Toole has produced over 300 pages of

documents from his personal files, which are copies of documents

relating to the warrants in which he was involved. 

Mr. Bonner seeks to compel the City to produce documents and

information relating to all 349 searches identified – even those

on which Officer O’Toole served as security or backup; he argues

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that he is entitled to documents and information even where

Officer O’Toole clearly had no role in obtaining the actual

warrant. The City and Officer O’Toole both argue that producing

discovery on the remaining 304 searches would be burdensome and

unreasonable, given any possible relevance. 

In the context of motions to compel, the Seventh Circuit

instructs that a “district court may grant or deny the motion in

whole or in part, and similar to ruling on a request for a

protective order under Rule 26(c), the district court may fashion

a ruling appropriate for the circumstances of the case.” Gile v.

United Air Lines, Inc., 95 F.3d 492, 496 (7th Cir. 1996). As with

all discovery matters, district courts have broad discretion in

determining motions to compel. See Peals v. Terre Haute Police

Dept., 535 F.2d 621, 629 (7th Cir. 2008); Reynolds v. Jamison,

488 F.3d 756, 761 (7th Cir. 2007).

Mindful that discovery should be liberally permitted, the

Court nonetheless finds, based upon the allegations in the

Complaint, that the City should not be required to produce

discovery relating to search warrants where Officer O’Toole was

not the affiant, did not himself seek and obtain the warrant at

issue. The Court does not see – and Mr. Bonner has not explained

– how such discovery is relevant to the claims alleged in this

lawsuit. In response to the defendants’ relevance argument, Mr.

Bonner simply asserts that discovery should be broad and that the

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defendants should not be permitted unilaterally to determine what

is and what is not relevant. Both of those assertions are true. 

But they do nothing to establish the relevance of the documents

requested. 

Moreover, the affidavit of Commander James O’Grady

demonstrates that requiring the City to retrieve and produce the

requested information on the remaining 304 searches would be

unduly burdensome. Accordingly, Mr. Bonner’s motion to compel is

denied. Mr. Bonner is entitled to the information requested on

the 45 searches on which Officer O’Toole was the affiant,

however, and, to the extent the City has not already done so, it

will immediately provide to Mr. Bonner all of the requested

documents related to those warrants. 

Mr. Bonner’s Motion to Strike

Mr. Bonner also asks the Court to strike the City’s requests

to admit, arguing that the requests are both overly burdensome

(numbered at 246) and inappropriate. Federal Rule of Civil

Procedure 36, which governs requests for admission, provides that

“[a] party may serve on any other party a written request to

admit, for purposes of the pending action only, the truth of any

matters within the scope of Rule 26(b)(1) relating to: (A) facts,

the application of law to fact, or opinions about either; and (B)

the genuineness of any described documents.” The Rule further

provides that, such matters are admitted “unless, within 30 days

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after being served, the party to whom the request is directed

serves on the requesting party a written answer or objection

addressed to the matter and signed by the party or its attorney.” 

The City served its requests to admit on October 1, 2012; Mr.

Bonner still has not responded. Instead, he moved to strike the

requests.

“Requests to admit aid the court and the parties by limiting

and refining the claims that will be asserted at trial”; “[a]s

such, they are generally quite important in resolving issues.” 

BP Amoco Chemical Co. v. Flint Hills Resources, No. 05 C 5661,

2008 WL 4542738 at *1 (N.D. Ill. June 11, 2008)(citing Taborn v.

Unknown Officers, No. 00 C 652, 2001 WL 138908, at *1 (N.D. Ill.

Feb. 16, 2001)). “No presumptive limit has ever been set on the

number of requests a party can propound”; instead, “lines have

been drawn on a case-by-case basis, depending on the complexity

of the case and whether or not the propounding party is truly

seeking admissions or seeking to circumvent the Federal Rules

regarding discovery.” Id. (citations omitted). Having said that,

the Court “must limit the frequency or extent of discovery . . .

if it determines that (I) the discovery sought is unreasonably

cumulative or duplicative, or can be obtained from some other

source that is more convenient, less burdensome, or less

expensive; . . . or (iii) the burden or expense of the proposed

discovery outweighs its likely benefit, considering the needs Of

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the case, the amount in controversy, the parties’ resources, the

importance of the issues at stake in the action, and the

importance of the discovery in resolving the issues.” Fed. R.

Civ. P. 26(b)(2)(C). 

 Here, the requests to admit were served on October 1, 2012 –

30 days before fact discovery was set to close. They asked Mr.

Bonner to admit, as of that date, that he had disclosed no

documents or witnesses to support his various claims, that he had

no documents or witnesses to support his various claims and that

he had no other evidence to support his various claims or the

elements thereof. There is nothing inappropriate about such

requests. These are facts. Although that number seems high, Mr.

Bonner’s complaint contains several Monell claims, each

consisting of multiple allegations and sub-allegations, and the

requests to admit track those parts and sub-parts. Thus, the

number itself is not particularly shocking. 

Additionally, although Mr. Bonner argues that he was

precluded from disclosing such documents and witnesses because of

the defendants’ failure to provide them, he could have answered

in the affirmative and reserved the right to supplement based

upon what the defendants provided in discovery. By October 1,

2012, with the discovery cutoff fast approaching, the defendants

had the right to test the waters on the issue, to be sure that

they were aware of the universe of documents and witnesses upon

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which Mr. Bonner would rely to pursue his claims. And,

certainly, there was nothing onerous about the requests – they

required no additional research or investigation on Mr. Bonner’s

part. Accordingly, the Court declines to strike the City’s

requests for admission. 

The City of Chicago’s Motion to Compel

As explained above, the City seeks an order compelling Mr.

Bonner to respond to contention interrogatories it served on July

18, 2012. A contention interrogatory allows a party to learn the

factual bases of the opposing party’s claims and defenses. See

Pratt v. Tarr, 464 F.3d 730, 733 (7th Cir. 2006). Rule 33

provides that interrogatories “may relate to any matter than may

be inquired into under Rule 26(b)” and that an interrogatory “is

not objectionable merely because it asks for an opinion or

contention that relates to fact or the application of law to fact

. . . .” Fed. R. Civ. P. 33(a)(2). Rule 33 does not allow

interrogatories that ask for purely legal conclusions, however.

See Nautilus Ins. Co. v. Raatz, No. 08 C 6182, 2011 WL 98843, at

*5 (N.D. Ill. Jan.12, 2011); 8B Fed. Prac. & Proc. Civ. § 2167.

The City’s interrogatories relate to the allegations that

form the basis of Mr. Bonner’s Monell claims. They ask Mr.

Bonner to spell out, with specificity, the allegations concerning

the misconduct referenced in his complaint, as well as the

evidence he has to support those allegations. In response to the

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City’s motion, Mr. Bonner claims that the City is hoarding

information and evidence, and then faulting him for failing to

tell it what that evidence is. But that is simply not the case. 

First, it is clear that the City and Office O’Toole have produced

myriad documents relating to searches and warrants for which

Officer O’Toole was the affiant. Second, the Court does not see

– and Mr. Bonner has not explained – how the evidence he seeks

(which, as explained above, he’s not going to get) would further

his Monell claims. And, finally, even if that evidence did do

what Mr. Bonner claims it would, he should still have provided

some form of an answer within the limits established by the rules

and by agreement of the parties – even if that answer simply

outlined his objections to the contention interrogatories. By

doing nothing, he has waived his right to object. 

In his response to the motion, Mr. Bonner claims that, in

the documents produced to date, he has been able to detect

patterns that would, in fact, support his Monell claims. If that

is indeed the case, responding to the relevant interrogatories

should be a simple matter. Yet he has, to date, declined to

respond to the City’s discovery. He is ordered to do so now. 

Officer O’Toole’s Motion to Compel

At his deposition, Mr. Bonner refused, on the advice of his

attorney, to answer certain questions. Officer O’Toole filed a

motion to compel, asking the Court to order Mr. Bonner: to sit

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for deposition again; to provide answers to the questions posed

relating to the state of his mental health; and to reimburse him

for the costs of the second deposition. Rather than file a

direct response to Officer O’Toole’s motion, counsel for Mr.

Bonner filed a motion to terminate or limit Mr. Bonner’s

deposition pursuant to Rule 30(d)(3), which Officer O’Toole has

moved to strike. 

During his deposition, counsel for Officer O’Toole asked Mr.

Bonner about his mental health issues. Mr. Bonner testified that

he saw both a therapist and a psychiatrist; additionally, he

testified, as part of a larger line of questioning, that he

discussed relationship issues with those professionals (Dr.

Williams and Dr. Jennings) both before and after the incident

covered in the Complaint, and that part of his care with those

doctors was related to his relationship issues. Bonner Dep.,

pp. 182-183. He testified that, at the time of his deposition,

he was not in a relationship, Bonner Dep., p. 180. But, when

counsel for Mr. O’Toole asked Mr. Bonner “[w]hen was the last

time you were in a relationship?” his attorney instructed him not

to answer. Bonner Dep., p. 180. Counsel for Mr. O’Toole asked

“[have] you been in any relationships after February of 2010?”;

again, his attorney instructed him not to answer. Bonner Dep.,

p. 182. Mr. Bonner testified that he was not in a relationship

at the time of the incident, Bonner Dep., pp. 185-186. When

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asked whether, in the last five years, he has ever been in a

relationship, he answered “yes.” Id., p. 188. When asked

whether, in the last five years he had ever discussed

relationship issues with Dr. Williams, counsel instructed him not

to answer. Id. Counsel indicated that she was unwilling to

allow him to answer anything prior to February 12, 2010. Id., p.

190. 

Rule 33 provides that “[a] person may instruct a deponent

not to answer only when necessary to preserve a privilege, to

enforce a limitation ordered by the court, or to present a motion

under Rule 30(d)(3).” There is no claim of privilege here; nor

has there been any relevant limitation ordered by the court. 

And, although counsel did file a motion under Rule 30(d)(3), she

clearly had no intention of filing it when she instructed Mr.

Bonner not to answer; indeed, the deposition occurred on October

11, 2012, and she didn’t file her motion until December 5, 2012,

(the very day her response to Officer O’Toole’s motion to compel

was due). Under the circumstances, counsel’s instruction was

inappropriate. 

Moreover, the position she took at the deposition was

untenable. Her client has alleged that the incident of February

12, 2010 exacerbated pre-existing issues (see, e.g., Plaintiff’s

answer to Defendant O’Toole’s interrogatory No. 10). And, as a

result, as the definition of exacerbates makes clear, the

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defendants are entitled to explore the state of affairs before

the incident, so that they can compare that to the state of

affairs after the incident. Given the damages claims, counsel

was wrong to preclude this line of questioning. The Court might

be inclined to limit this line of questioning if, as counsel

suggests, the questions were truly invasive or designed to harass

Mr. Bonner because of his sexual preference. But the record

makes clear that that was not the case. The questions asked only

about “relationships,” without ever even hinting at the gender of

the person involved, and they asked nothing about the specifics

discussed with the doctors. There was simply no basis for

counsel to limit the questions as she did. 

In his complaint, Mr. Bonner has alleged that the incident

he describes caused damages to his physical and mental health. 

By claiming damages relating to his mental health, Mr. Bonner has

put the matter at issue. And, having opened the door, he cannot

refuse to provide discovery on the topic; the defendants are

entitled to explore the issue. Accordingly, the Court finds that

he must answer the questions posed. Additionally, because

counsel for Mr. Bonner inappropriately limited discovery, she is

ordered to reimburse counsel for Officer O’Toole for the costs of

reconvening Mr. Bonner’s deposition, should he choose to do so. 

Conclusion

For the reasons set forth above, the Court denies Mr.

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Bonner’s Motion to Compel [#48]; grants the City’s motion to

compel [#57]; grants Officer O’Toole’s motion to compel [#62];

and grants Officer O’Toole’s motion to strike [#92]. Mr.

Bonner’s motion to terminate or limit his deposition [#88] is

denied. Mr. Bonner is ordered to provide substantive responses

to the City’s interrogatories by January 10, 2013; any objections

to those interrogatories are waived. Additionally, to the extent

counsel for Officer O’Toole still wishes to pursue answers to the

questions counsel barred (relating to relationship issues that

played a role in his mental health treatment during the last five

years), Mr. Bonner is directed to provide such answers; his

attorney is ordered to reimburse counsel for the costs of

deposing him a second time. 

Dated: December 18, 2012

E N T E R:

______________________________

ARLANDER KEYS

United States Magistrate Judge

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