UNITED STATES DISTRICT COURT

FOR THE NORTHERN DISTRICT OF ILLINOIS

EASTERN DIVISION

PROTECTIVE INSURANCE )

COMPANY, )

) Case No. 20-cv-03611

Plaintiff/Counter-Defendant, )

) Judge Sharon Johnson Coleman

v. )

)

DARRELL BOLDEN, )

)

Defendant/Counter-Plaintiff )

MEMORANDUM OPINION AND ORDER

Plaintiff Protective Insurance Company (“Protective”) brought this action for declaratory 

judgment against Darrell Bolden (“Bolden”). Bolden filed counterclaims for declaratory judgment 

and breach of contract. Bolden now moves for leave to amend his counterclaim to add another 

claim under 215 ILCS 5/155. For the reasons stated below, the Court denies Bolden’s motion [34].

Background

The Court presumes familiarity with its recent ruling denying Protective’s motion for 

summary judgment [46] and granting Bolden’s motion for summary judgment [39]. On August 20, 

2018, Bolden was in a car accident (the “Accident”) while driving a 2007 Freightliner commercial 

delivery truck for his employer Team Strategic, Inc. (“Team Strategic”). Team Strategic maintained 

an insurance policy with Protective for its vehicles (the “Policy”). At the time of the Accident, the 

2007 Freightliner was not listed as a scheduled auto in the Policy. Instead, the Policy listed a 1998 

Freightliner that had been totaled in a car accident in September 2017. Bolden contended, and the 

Court later held, that the 2007 Freightliner served as a temporary substitute for the totaled truck, 

affording him coverage under the Policy. Protective denied coverage because one of Team 

Strategic’s owners, Carmelo Soto (“Soto”), retroactively terminated coverage for the 1998 

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Freightliner the day after the Accident. Therefore, Protective argued, the 2007 Freightliner could 

not serve as a temporary substitute for a vehicle that did not have coverage for the Accident.

Discussion

Under Federal Rule of Civil Procedure 15(a)(2), “[t]he court should freely give leave to 

amend when justice so requires.” But if the new pleading would not survive a motion to dismiss, 

the Court may refuse to entertain an amendment on grounds of futility. Gandhi v. Sitara Cap. Mgmt., 

LLC, 721 F.3d 865, 869 (7th Cir. 2013) (citing Brunt v. SEIU, 284 F.3d 715, 720–721 (7th Cir. 

2002)). To state a claim under 215 ILCS 5/155, the insured must show that the insurance company 

acted vexatiously and unreasonably in its delay to settle the insured’s claim. If successful on such a 

claim, the insured is entitled to reasonable attorney fees and other costs. But where there is a bona 

fide dispute regarding coverage, statutory sanctions under Section 155 are inappropriate. Consolidated 

Chassis Mgmt. LLC v. Northland Ins. Co., No. 19-cv-5287, 2020 WL 6262377, at *5 (N.D. Ill. October 

23, 2020) (Durkin, J.) (citing Golden Rule Ins. Co. v. Schwartz, 786 N.E.2d 1010, 1018 (Ill. 2013)). 

Bolden argues that Protective disclosed new evidence that the insurance company failed to 

properly investigate his claim and ignored facts establishing that Team Strategic used the 2007 

Freightliner as a temporary substitute. However, this same evidence shows that Protective 

consistently denied coverage on the basis that Soto’s retroactive termination of coverage precluded 

Bolden’s claim. (Dkt. 38-1.) Though the Court ruled in Bolden’s favor on his motion for summary 

judgment, a bona fide dispute clearly existed as to whether coverage had been effectively terminated

retroactively. Therefore, Bolden’s proposed new counterclaim would not survive a motion to 

dismiss and the Court denies his motion to amend.

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Conclusion

For the foregoing reasons, the Court denies Defendant’s motion for leave to amend his 

counterclaims [34].

IT IS SO ORDERED. 

Date: 3/21/2022

Entered: _____________________________

 SHARON JOHNSON COLEMAN

 United States District Judge

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