UNITED STATES DISTRICT COURT

FOR THE NORTHERN DISTRICT OF ILLINOIS

EASTERN DIVISION

SYLVESTER BONNER, JR.,

Plaintiff, 

v. 

DANIEL O’TOOLE, 

Defendant. 

No. 12 CV 981 

Judge Manish S. Shah 

ORDER

Defendant O’Toole’s motion for summary judgment on the conspiracy claim, 

[251] (briefed at [311], [322]), is granted. Plaintiff Bonner’s cross-motion, [276] 

(briefed at [315]), is denied. Bonner’s motion for reconsideration of the court’s ruling 

on O’Toole’s liability for the electronic equipment, [318], is granted in part. Bonner 

has waived the argument that the police officers stole the equipment, and may not 

seek damages for the theft under a due-process theory of liability, but may present at 

trial evidence that the theft was proximately caused by O’Toole’s unlawful entry into 

Bonner’s apartment. 

STATEMENT

Sylvester Bonner sued Officer Daniel O’Toole and other “unknown officers” of 

the Chicago Police Department, as well as the City of Chicago, after a team of officers 

broke down the door to Bonner’s apartment and left his belongings damaged and in 

disarray while executing a search warrant. Bonner claimed that the warrant was 

ambiguous as to the place to be searched (the police were looking for an apartment 

inhabited by a woman named “Shu-Shu”), and so the officers violated Bonner’s 

Fourth Amendment rights by searching his apartment. Bonner also alleged that 

several items in his apartment—a cellphone, computer, and surround-sound 

system—were unlawfully seized. In addition to the Fourth Amendment claim 

(brought under 42 U.S.C. § 1983), Bonner also brought against the officers a 

civil-conspiracy claim (also under § 1983). Bonner sued the City under Monell v. Dep’t 

of Soc. Servs. of City of N.Y., 436 U.S. 658 (1978). 

The City and O’Toole each filed a motion for summary judgment on the claims 

against them; Bonner cross-moved for summary judgment (on liability only) on all of 

his claims. Bonner’s motion was granted, and O’Toole’s denied, as to the unlawful 
2 

entry of Bonner’s apartment. The warrant did not satisfy the particularity 

requirement of the Fourth Amendment, and Officer O’Toole should have known of 

the ambiguity based on recent searches at the same apartment complex. As for the 

disappearance of the electronic equipment, I determined that Bonner was no longer 

asserting the police had stolen those items, and awarded summary judgment to 

O’Toole. 

Neither Bonner nor O’Toole was granted summary judgment on the 

civil-conspiracy claim. Although both parties had moved for judgment on that claim, 

neither had argued it. The City of Chicago, however, did argue against liability on 

the civil-conspiracy claim. Bonner neglected to respond to that argument, and the 

City’s motion was granted on the conspiracy issue. The motion was also granted to as 

to the City’s liability under Monell for O’Toole’s Fourth Amendment violation. The 

unknown-officer defendants, whose identities were still unknown at summary 

judgment, were dismissed from the case. 

I requested supplemental briefing from O’Toole and Bonner on the conspiracy 

claim, limited to the facts set out in the parties’ existing Local Rule 56.1 statements. 

Bonner’s motion for reconsideration of this request, [315], was denied. [317].1 Bonner 

filed a second motion for reconsideration under Federal Rule of Civil Procedure 54(b), 

seeking revision of the court’s ruling that Bonner could not recover under Section 

1983 for the theft of his electronic equipment (or, in the alternative, seeking leave to 

amend his complaint). [318]. 

The Conspiracy Claim 

A conspiracy is a combination of two or more individuals, acting in concert to 

commit an unlawful act. Beaman v. Freesmeyer, 776 F.3d 500, 510 (7th Cir. 2015) 

(citing Scherer v. Balkema, 840 F.2d 437, 441 (7th Cir. 1988)). To establish 

conspiracy liability under Section 1983, the plaintiff must show: (1) that the 

individuals reached an agreement to deprive him of his constitutional rights; and 

(2) overt acts in furtherance of that agreement that actually deprived him of those 

rights. Id. (citing Scherer, 840 F.2d at 442). Circumstantial evidence may be used to 

demonstrate a conspiracy, “but such evidence cannot be speculative.” Id. at 511 

(citing Williams v. Seniff, 342 F.3d 774, 785 (7th Cir. 2003)). 

O’Toole argues in his supplemental summary-judgment brief that the 

conspiracy claim must fail because, at this point in the litigation, he is the only 

 

1 Citations to the record are designated by the document number as reflected on the district 

court’s docket, enclosed in brackets; referenced page numbers are from the CM/ECF header 

placed at the top of filings. 
3 

defendant left in the case. O’Toole cannot have conspired with himself. See Gagan v. 

American Cablevision, Inc., 77 F.3d 951, 966 (7th Cir. 1996) (“[T]here can be no 

conspiracy of one.”) But that is not what Bonner is claiming. Bonner claims that 

O’Toole conspired with the other officers who searched Bonner’s apartment. That 

those other officers are no longer parties to the suit is immaterial. To prevail on a 

conspiracy claim against O’Toole, Bonner must show only that O’Toole reached an 

agreement with one or more persons to violate Bonner’s rights, and overt acts in 

furtherance of that agreement. If O’Toole entered into a conspiracy, he is responsible 

for others’ acts within the scope of the agreement. See Bank of America, N.A. v. 

Knight, 725 F.3d 815, 818 (7th Cir. 2013). 

O’Toole argues next that there cannot have been an agreement to violate 

Bonner’s constitutional rights, because the officers did not know that the apartment 

they were about to search was his. The officers thought the apartment belonged to a 

woman named “Shu-Shu,” since it was she, and not Bonner, who was the target of the 

warrant. This argument, too, is unavailing. As explained in the earlier order on the 

motions for summary judgment, warrants cannot be executed by persons who know 

them to be ambiguous. See [295] at 23–24. To the extent O’Toole agreed with another 

officer to execute an ambiguous search warrant, he agreed to violate the rights of 

whoever lived in the location searched. This person was Bonner. 

O’Toole is correct, however, that Bonner has not presented evidence from 

which it may be inferred that O’Toole reached an agreement with another officer to 

execute an ambiguous warrant. Bonner says that such an agreement was reached at 

the “pre-raid meeting” on February 12, 2010. It was at this meeting that O’Toole and 

another officer, Sergeant Stec, briefed the search-team members about the warrant 

to search “[t]he entire 1st floor apartment” at 4929 W. Adams, and conveyed to the 

officers information obtained from a police informant (i.e., that “Shu-Shu’s” 

apartment was the first door on the right after entering the building). See [283] at 14 

¶¶ 40, 44; [297-8]. At least some members of the search team, along with O’Toole and 

Sergeant Stec, had already searched another apartment at the same complex a few 

weeks before. See [283] at 14 ¶ 43; [291] at 6–7 ¶ 21. According to the warrant for that 

apartment, it was also a “first-floor” unit. See [279-6]. But the officers had climbed a 

flight of stairs in order to reach it. See [291] at 7 ¶ 22. 

These facts fall short of demonstrating the kind of agreement necessary to 

suggest collusion by Officer O’Toole. Perhaps some of the officers at the pre-raid 

meeting recalled having searched, in the same complex, an above-ground “first-floor” 

apartment several weeks prior. It is at least possible, then, that those same officers 

wondered if the “first-floor” descriptor in the February 12 warrant was accurate, 

given that the February 12 warrant, if based on the informant’s description, was in 

theory targeting a ground-floor unit. But there is no evidence of an understanding 
4 

with O’Toole about the warrant’s flaws—and thus no evidence of an agreement to 

knowingly execute a defective warrant. See Sow v. Fortville Police Dep’t, 636 F.3d 

293, 305 (7th Cir. 2011) (requiring, for proof of a civil conspiracy, “evidence that 

would permit a reasonable jury to conclude that a meeting of the minds had 

occurred”) (emphasis added) (citation omitted). Bonner’s evidence of an unlawful 

agreement at the pre-raid meeting is purely speculative, and that is not enough to 

defeat summary judgment on the conspiracy claim. 

If no agreement was reached at the pre-raid meeting, says Bonner, then one 

was formed after the search team arrived at the apartment complex—at which point, 

he argues, the officers would have realized that the warrant was too vague. Bonner 

claims that the letters “BA” were affixed to his front door, indicating a 

basement-level (not first-level) apartment, and notes that there was a second 

apartment door across from his own—suggesting that the warrant’s reference to 

“[t]he entire 1st floor apartment” was overbroad. See [291] at 5–6 ¶ 19. Also, says 

Bonner, there were too many doorbells on the outside of the building, and too many 

mailboxes in the entryway, for there to have been just one unit per floor. See id. at 5 

¶¶ 17–18. O’Toole contends that none of the officers saw the doorbells and mailboxes 

or the second apartment door, and disputes that the letters on Bonner’s own door 

were actually present on February 12, 2010. See id. at 5–6 ¶¶ 17–19. Even assuming 

that the letters were there, and that someone on the search team spotted them (or 

saw other indicia of the warrant’s possible vagueness), that is not enough to show a 

conspiracy with Officer O’Toole. For a reasonable juror to conclude that O’Toole 

agreed with another officer to execute an imprecise warrant, there must be evidence 

of a meeting of the minds about the ambiguity. Here there is none. We are left 

instead with conjecture, an inadequate substitute. 

The conspiracy claim is superfluous in any event. In the typical case, 

conspiracy claims matter only with respect to private-actor defendants, because state 

actors, like O’Toole, may be sued directly under Section 1983. See Logan v. Wilkins, 

644 F.3d 577, 583 n. 1 (7th Cir. 2011); Hoskins v. Poelstra, 320 F.3d 761, 764 (7th Cir. 

2003); cf. Fairley v. Andrews, 578 F.3d 518, 526 (7th Cir. 2009) (discussing conspiracy 

claims under 42 U.S.C. § 1985(3)); Scott v. City of Chicago, — F. App’x —, No. 

15-1281, 2015 WL 6688043, at *1 (7th Cir. Nov. 2, 2015) (“All of the defendants in 

this suit . . . are public employees . . . , which means that a conspiracy claim has no 

role to play.” (citing Fairley, 578 F.3d at 526)). O’Toole’s liability under Section 1983 

has already been determined, and, as stated in the court’s earlier order, he is liable to 

Bonner for any damages caused by the execution of the February 12, 2010 warrant. 

See [295] at 24. To the extent Bonner seeks to establish the same liability through a 

conspiracy claim, that claim is duplicative. Bonner may have but one recovery for his 

injuries. See Swanigan v. City of Chicago, 775 F.3d 953, 963 (7th Cir. 2015). 
5 

For the reasons discussed above, O’Toole’s motion for summary judgment on 

the civil-conspiracy claim (Count VI) is granted. Bonner’s cross-motion on that claim 

is denied. 

Bonner’s Motion for Reconsideration 

Bonner has also filed a motion under Federal Rule of Civil Procedure 54(b), 

seeking reconsideration of the April 3, 2015 ruling that Bonner cannot recover for the 

theft of his electronic equipment. I determined that Bonner could not recover from 

O’Toole any damages for the theft of these items because: (1) Bonner was no longer 

contending that the police officers removed the electronics items from his apartment 

(and seizures by private individuals generally are not covered by the Fourth 

Amendment); and (2) the theft of the items by a third party was not a foreseeable 

consequence of the unlawful entry. See [295] at 26–27. 

O’Toole argues that the motion must be denied as untimely because it is 

governed by Rule 59(e), which imposes a 28-day filing window—a window that 

Bonner missed. Rule 59(e) applies to motions to “alter or amend a judgment.” Fed. R. 

Civ. P. 59(e). But partial summary judgment (and that is what the court’s earlier 

ruling was, as only liability was decided) is not a final entry of “judgment” within the 

meaning of Rule 59. See Deimer v. Cincinnati Sub-Zero Prods., Inc., 990 F.2d 342, 

346 (7th Cir. 1993) (citing 10A Charles A. Wright, et al., Federal Practice and 

Procedure § 2737, at 455–56 (2d ed. 1983); Minority Police Officers Ass’n of South 

Bend v. City of South Bend, Ind., 721 F.2d 197, 200 (7th cir. 1983)). Bonner’s motion 

may properly be considered under Rule 54(b). See Fed. R. Civ. P. 54(b) (“[A]ny order 

or other decision . . . that adjudicates fewer than all the claims or the rights and 

liabilities of fewer than all the parties . . . may be revised at any time before the entry 

of a judgment adjudicating all the claims and all the parties’ rights and liabilities.”). 

Bonner argues first that the court erred in concluding he had abandoned his 

Fourth Amendment claim that the police officers took his electronics. Bonner says 

that what he alleged in Count V of his complaint, and the facts he included in his 

Local Rule 56.1 statement at summary judgment, implied either that the police took 

the equipment or that someone else did as a result of the officers’ failure to properly 

secure Bonner’s door after their search. See [318] at 2–4. What Bonner alleged in his 

complaint is of little consequence at this stage of the case, as it is now the evidence 

that counts. See Whitman v. Nesic, 368 F.3d 931, 933–34 (7th Cir. 2004) (explaining 

that a plaintiff may not rest on his pleadings at the summary-judgment stage); 

Goodman v. Nat’l Sec. Agency, Inc., 621 F.3d 651, 654 (7th Cir. 2010) (observing that 

summary judgment is “the ‘put up or shut up’ moment in litigation, [when] the 

non-moving party is required to marshal and present the court with the evidence [he] 

contends will prove [his] case”) (citations omitted). Bonner says he presented 
6 

evidence that could have been interpreted to support either theory of liability.2 But 

in response to O’Toole’s motion for summary judgment, Bonner made clear which 

theory he was relying on—and it wasn’t that the police had stolen the equipment 

themselves. 

O’Toole had argued, “As to property taken from BONNER’s apartment, there 

is no evidence of O’TOOLE, or any officer for that matter, removing items from 

BONNER’s residence. [266] at 14. Bonner in turn argued: 

In performing a “thorough” search [of Bonner’s apartment], O’Toole 

strew plaintiff’s personal belongings, clothes, and food all over the 

apartment. Furthermore, O’Toole left the apartment unsecured and, as a 

result, plaintiff’s computer, cell phone, and sound system were stolen. 

O’Toole cannot blame others who may have taken plaintiff’s computer, 

cell phone, and sound system, in that it was his illegal conduct that 

caused the loss. 

[277] at 16 (emphasis added). Nowhere in Bonner’s brief did he respond to the 

argument that there is no evidence of the police taking the equipment. See also

Plaintiff’s Response to Defendant Daniel O’Toole’s Statement of Undisputed 

Material Facts, Local Rule 56.1, [283] at 30 ¶ 96 (O’Toole wrote, “Nothing was taken 

out of the apartment by any officers and nobody tore open any clothing. [Citation to 

exhibits.].” Bonner responded, “a) After the police left, Michael Dudley, the 

maintenance man, took measurements of the door to Mr. Bonner’s apartment and 

then left to go to his shop across the alley to cut the boards to board up the door. 

[Citations.] b) With the door unlocked, it would only take a couple of minutes for 

someone to steal things from the apartment. [Citations.] c) When Sylvester Bonner 

came home, he found the front door broken and boarded up, his personal belongings 

in disarray, the lining of his fur coats cut as if the police were looking for drugs, and 

his computer, sound system, and cell phone missing. [Citations.]”) (emphases added). 

Bonner has waived the issue. See Goodpaster v. City of Indianapolis, 736 F.3d 1060, 

1075 (7th Cir. 2013); Bonte v. U.S. Bank, N.A., 624 F.3d 461, 466 (7th Cir. 2010). 

 

2 Bonner highlights certain statements of fact from his Rule 56.1 submission. See [318] at 3 

(asserting that the apartment was left without a lockable front floor, there were no 

photographs taken of the search, the maintenance man left the apartment unlocked for some 

time after the police left, and O’Toole later admitted that the police searched the wrong 

apartment but denied that anything was missing; O’Toole also said the police had pictures to 

prove that nothing was missing) (citing [278] at 13–14 ¶¶ 75–81). These facts do not support 

an inference that the police took the electronics. 
7 

However, Bonner’s second argument for reconsideration—that I should not 

have granted judgment to O’Toole on the basis of causation—is well-taken. I 

determined in the earlier ruling that Bonner could not recover damages for the stolen 

electronics because their theft was not a foreseeable consequence of O’Toole’s 

unlawful entry into Bonner’s apartment. But O’Toole never addressed whether the 

theft was proximately caused by his unconstitutional conduct, and though Bonner 

did address this, his analysis was a cursory one. See [277] at 17. Thus, while it was 

proper to deny Bonner’s motion as to O’Toole’s liability for the stolen items, O’Toole 

was not entitled to judgment. Bonner should be afforded another opportunity to 

marshal evidence on this point. See Hotel 71 Mezz Lender LLC v. Nat’l Retirement 

Fund, 778 F.3d 593, 602–05 (7th Cir. 2015).3 Bonner’s motion for reconsideration is 

therefore granted in part: Bonner may present to the jury evidence concerning who 

proximately caused the theft of the electronic equipment. 

Bonner may not, however, seek damages for the stolen equipment based on a 

due-process theory of liability. He cites Whitaker v. Milwaukee Cnty., Wis., 772 F.3d 

802, 809 (7th Cir. 2014), for the proposition that he may, but his reliance on Whitaker 

is misplaced. In that case, the plaintiff had presented in opposition to summary 

judgment a new theory of legal liability, but was precluded by the district court from 

relying on it. See 772 F.3d at 807. The Seventh Circuit determined that the plaintiff 

should have been allowed to argue her new theory at the summary-judgment stage, 

because it was based on the same fundamental facts as those alleged in her 

complaint. See id. at 808–09. Whitaker is inapposite here: even if Bonner’s 

due-process theory ultimately stems from facts set forth in his original pleading, he 

did not present that new theory at summary judgment. He instead waited to raise 

the issue until after the summary-judgment motions had been resolved. This was too 

 

3 Bonner argues that the court should not have addressed causation at all, because causation 

is a damages issue, and Bonner moved for summary judgment only on liability. See [318] at 

10. Bonner is not quite correct. Causation may sometimes be addressed at the damages stage 

of the litigation. See, e.g., Guzman v. City of Chicago, 689 F.3d 740, 745 (7th Cir. 2012); 

Wehrs v. Wells, 688 F.3d 886, 892 (7th Cir. 2012) (“Because a plaintiff must ordinarily prove 

damages, [a] defaulting party may raise the issue of causation as it relates to the calculation 

of damages.”) (citation omitted). But causation may also inform a determination of liability. 

See Whitlock v. Brueggemann, 682 F.3d 567, 582 (7th Cir. 2012) (explaining, in addressing 

qualified immunity for an alleged due-process violation, that “[c]ausation is a standard 

element of tort liability”); see also Belbachir v. County of McHenry, 726 F.3d 975, 982 (7th 

Cir. 2013) (stating that causation is “an elementary requirement of liability”); United States 

v. King-Vassel, 728 F.3d 707, 714 (7th Cir. 2013) (“[A]n action that breaks the chain of 

causation would relieve a defendant of liability.”). That Bonner himself understood causation 

to be a part of the liability inquiry is demonstrated by his having raised the proximate-cause 

issue in his motion for summary judgment—which, as Bonner emphasizes here, did not 

address damages. 
8 

late. While Bonner was not required to plead specific legal theories in his complaint, 

see id. at 808, “[t]here must be a point at which a plaintiff makes a commitment to 

the theory of [his] case,” Thompson v. Boggs, 33 F.3d 847, 853 (7th Cir. 1994) (citation 

omitted). Bonner made such a commitment at summary judgment; he may not now, 

on the eve of trial, inject into the proceedings a claim that he could have asserted all 

along but did not. Cf. Bethany Pharmacal Co., Inc. v. QVC, Inc., 241 F.3d 854, 861 

(7th Cir. 2001) (observing that the district court does not abuse its discretion in 

denying a motion to amend where the plaintiff, “if it had prepared for th[e] litigation 

with the appropriate foresight,” could have included the additional claim in its 

original complaint). Accordingly, Bonner’s alternative request for leave to amend his 

complaint to include a due-process claim, see [318] at 13, is denied. 

ENTER: 

Date: 11/17/15 

 Manish S. Shah 

 U.S. District Judge