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IN THE UNITED STATES DISTRICT COURT

FOR THE SOUTHERN DISTRICT OF FLORIDA (Key West)

BIANCA N. DIGENNARO, as the Civil Action No.: 4:20-cv-10094

legal guardian of HMM, a minor,

JURY TRIAL DEMANDED

Plaintiff, CIVIL ACTION – LAW

v. Chief Judge: K. Michael Moore

MICHAEL L. MALGRAT,

KENNETH JW WAITE,

FRED C. SIMS,

ASHLEY N. HENRIQUEZ,

KYLE SHEER,

FRAN HERIN, and

CITY OF KEY WEST, FLORIDA,

Defendants.

AMENDED COMPLAINT

AND NOW comes the Plaintiff, BIANCA N. DIGENNARO, as the legal 

guardian of HMM, a minor, by and through her counsel, DEVON M. JACOB, 

ESQUIRE, of the law firm of JACOB LITIGATION, INC.; and BENJAMIN L. 

CRUMP, ESQUIRE, of BEN CRUMP LAW, PLLC; to aver the following:

JURISDICTION AND VENUE

1. This action is brought pursuant to 42 U.S.C. § 1983. 

2. Jurisdiction is founded upon 28 U.S.C. §§ 1331, 1343, and 1367. 

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3. Venue is proper in this Court, as all parties are located within the 

Southern District of Florida, and the cause of action arose in the Southern District of 

Florida.

PARTIES

4. Plaintiff, BIANCA N. DIGENNARO (“DIGENNARO”), is an adult 

individual, who lives in the Southern District of Florida. DIGENNARO is the 

biological mother and legal guardian of HMM, a minor. 

5. Defendant, MICHAEL L. MALGRAT (“MALGRAT”), is an adult 

individual, who during all relevant times, was employed by the Key West Police 

Department, as a police officer. All of Defendant MALGRAT’S actions or inactions 

were taken under color of state law. He is sued in his individual capacity.

6. Defendant, KENNETH JW WAITE (“WAITE”), is an adult individual, 

who during all relevant times, was employed by the Key West Police Department, 

as a police officer. All of Defendant WAITE’S actions or inactions were taken under 

color of state law. He is sued in his individual capacity.

7. Defendant, FRED C. SIMS (“SIMS”), is an adult individual, who 

during all relevant times, was employed by the Key West Police Department, as a 

police officer. All of Defendant SIMS’ actions or inactions were taken under color 

of state law. He is sued in his individual capacity.

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8. Defendant, ASHLEY N. HENRIQUEZ (“HENRIQUEZ”), is an adult 

individual, who during all relevant times, was employed by the Monroe County 

School District and/or Gerald Adams Elementary, as a teacher. All of Defendant 

HENRIQUEZ’S actions or inactions were taken under color of state law. She is sued 

in her individual capacity.

9. Defendant, KYLE SHEER (“SHEER”), is an adult individual, who 

during all relevant times, was employed by the Monroe County School District 

and/or Gerald Adams Elementary, as an Assistant Principal. All of Defendant 

SHEER’S actions or inactions were taken under color of state law. He is sued in his 

individual capacity.

10. Defendant, FRAN HERIN (“HERIN”), is an adult individual, who 

during all relevant times, was employed by the Monroe County School District 

and/or Gerald Adams Elementary, as a Principal. All of Defendant HERIN’S actions 

or inactions were taken under color of state law. She is sued in her individual 

capacity.

11. Defendant, CITY OF KEY WEST, FLORIDA (“CITY”), owns and 

operates the Key West Police Department.

MATERIAL FACTS

12. The Monroe County School District (“School District”) operates 

Gerald Adams Elementary, 5855 College Avenue, Key West, Florida 33040.

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13. During all relevant times, ASHLEY N. HENRIQUEZ 

(“HENRIQUEZ”) was employed by the School District and/or Gerald Adams 

Elementary, as a teacher.

14. During all relevant times, KYLE SHEER (“SHEER”) was employed 

by the School District and/or Gerald Adams Elementary, as an Assistant Principal.

15. During all relevant times, FRAN HERIN (“HERIN”) was employed by 

the School District and/or Gerald Adams Elementary, as a Principal.

16. During all relevant times, HMM was an elementary school student in 

the School District.

17. The School District knew that HMM had a diagnosis of Oppositional 

Defiance Disorder and Adjustment Disorder with Mixed Disturbance of Emotional 

Conduct.

18. During all relevant times, HERIN, SHEER, and HENRIQUEZ, knew 

that HMM had a Positive Behavioral Intervention Plan (PBIP) and an Individual 

Educational Plan (“IEP”).

19. The IEP noted the primary exceptionality as emotional or behavioral 

disability.

20. The IEP noted the aforementioned diagnoses, in addition to a diagnosis 

of Attention Deficit Hyperactivity Disorder (“ADHD”).

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21. The School District and Gerald Adams Elementary classified HMM as 

having an “Emotional or Behavioral Disability.”

22. The CITY OF KEY WEST, FLORIDA (“CITY”) owns and operates 

the Key West Police Department.

23. On December 14, 2018, KENNETH JW WAITE (“WAITE”), FRED 

C. SIMS (“SIMS”), and MICHAEL L. MALGRAT (“MALGRAT”), were 

employed by the Key West Police Department, as police officers.

24. Police officers employed by the Key West Police Department are 

assigned to certain schools in Monroe County, including Gerald Adams Elementary.

25. The police officers are responsible for the protection and safety of 

school personnel, property, and students within the school district. 

26. The police officers perform general law enforcement duties, present 

law-related education programs, identify students displaying early signs of 

delinquency, and serve as a referral resource for students, faculty, and parents.

27. On December 14, 2018, MALGRAT was working at Gerald Adams 

Elementary as a School Resource Officer (“SRO”).

28. School employees are permitted to use “reasonable physical force” 

against students “to maintain a safe learning environment.”

29. The IEP and BIP, however, did not permit the use of any force against 

HMM.

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30. Rather, to the exclusion of physical force, the BIP listed non-physical 

responses to be utilized with HMM to maintain a safe learning environment.

31. Furthermore, neither the IEP nor the BIP provided for the use of police 

officers, handcuffs, or verbal intimidation, i.e., scared straight tactics, for purposes 

of teaching a child a disciplinary lesson or for behavioral modification.

32. As such, in response to a minor disciplinary matter, no force would be 

objectively reasonable.

33. On or about December 14, 2018, HENRIQUEZ, who was not HMM’s 

regular teacher and who was not well known to HENRIQUEZ, was assigned to 

supervise HMM.

34. At the time, HMM was 8 years old, only approximately 3 feet 6 inches

tall, and 64 pounds.

35. On the same date, HENRIQUEZ reported to HERIN, SHEER, and/or 

MALGRAT that HMM had refused to sit on a bench properly despite requests that 

he do so.

36. HENRIQUEZ further reported that when HMM refused to comply, she 

requested that HMM come sit next to her.

37. HENRIQUEZ further reported that when HMM again refused to 

comply, she got up, and walked over to him.

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38. HENRIQUEZ further reported that she went hands-on in an attempt to 

physically move HMM, and as she did so, HMM told her not to put her hands on 

him.

39. HENRIQUEZ further reported that when she did not let go of HMM, 

HMM “punched” her once in the chest with his right hand.

40. HENRIQUEZ was not injured and did not report being injured.

41. Moreover, HENRIQUEZ understood that HMM had not “punched” her 

as the word “punch” is commonly used.

42. Rather, HENRIQUEZ understood that while HMM was attempting to 

pull his arm away from her grasp, his arm apparently inadvertently made contact 

with her body.

43. As such, HENRIQUEZ knew that no credible threat to the school or its 

occupants ever existed, and that police intervention was neither necessary nor 

appropriate.

44. Similarly, based on HENRIQUEZ’S report, HERIN, SHEER, and 

MALGRAT, also knew that no credible threat to the school or its occupants ever 

existed, and that police intervention was neither necessary nor appropriate.

45. HERIN, SHEER, and MALGRAT did not interview HMM to find out 

his version of the events.

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46. Had HERIN, SHEER, and/or MALGRAT interviewed HMM and other 

available witnesses, and reviewed security video that is believed to have existed, 

they would have confirmed that no credible threat to the school or its occupants ever 

existed, no crime had been committed, and that police intervention was neither 

necessary nor appropriate.

47. Had MALGRAT interviewed HMM and other available witnesses, and 

reviewed security video that is believed to have existed, he would have confirmed

that probable cause did not exist to criminally charge HMM with any crime; let alone 

with felony battery.

48. Pursuant to FED.R.CIV.P. 11(b)(3), the following factual contentions 

will likely have evidentiary support after a reasonable opportunity for further 

investigation or discovery:

a. Due to HMM’S disability and the mishandling of same by school 

officials, HMM had an extensive “disciplinary” history in the school.

b. HERIN, SHEER, HENRIQUEZ, and/or MALGRAT, summoned 

WAITE and SIMS to the school for an unlawful purpose, i.e., for the purpose of 

teaching HMM a lesson and trying to scare HMM into “behaving” in the future.

c. In doing so, HERIN, SHEER, HENRIQUEZ, and/or MALGRAT

knowingly acted outside of their respective policies and training.

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d. HERIN, SHEER, HENRIQUEZ, and/or MALGRAT’s actions set in 

motion a series of events that resulted in HMM being taken into custody by WAITE 

and SIMS.

49. HERIN, SHEER, HENRIQUEZ, and MALGRAT, had a duty not to 

turn physical custody of HMM over to WAITE and SIMS, for an unlawful purpose.

50. When WAITE and SIMS arrived, HMM was sitting on a bench, in the 

hallway just outside of the school office, in clear view of HERIN and SHEER.

51. The incident for which WAITE and SIMS had been summoned had 

ended.

52. HMM was sitting quietly and calmly, and was visibly upset and scared.

53. In an attempt to teach HMM a lesson and try to scare him into 

“behaving” in the future, despite knowing that HMM was not “going to jail” (in the 

common understanding of that statement), WAITE, SIMS, and MALGRAT, 

intentionally led HMM to believe that he was going to jail.

54. Specifically, WAITE, SIMS, and/or MALGRAT, stated to HMM, “So 

you know where you are going? You are going to jail. So you need to stand up and 

put your hands behind your back.”

55. In a further attempt to teach HMM a lesson and try to scare him into 

“behaving” in the future, despite the fact that HMM was not a physical threat to 

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himself or others, WAITE, SIMS, and MALGRAT, handcuffed and/or permitted 

HMM to be handcuffed.

56. Referencing the handcuffs, WAITE, SIMS, and MALGRAT, stated, 

“You can justify it,” and “You can try it.”

57. HMM was so young and physically small, however, that after the 

handcuffs were applied, it was determined that they were too big and could not be 

properly used on HMM.

58. As such, the handcuffs were removed and HMM was told to simply 

walk with his hands in front of him.

59. Visibly upset and scared, HMM asked for his dad.

60. Despite his dad still being in the building, WAITE, SIMS, and/or 

MALGRAT, told HMM that his dad had left the school.

61. Before exiting the building, WAITE, SIMS, and MALGRAT stated, 

“You understand this is very serious, ok? And, I hate that you put me in this position 

that I have to do this. Ok? Alright? The thing about it is, you made a mistake now it 

is time to learn from it and grow from it. Right? Not repeat the same mistake again. 

Ok? Alright.”

62. HMM was then escorted out of the building and to a marked patrol 

vehicle.

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63. HMM was then permitted to enter the rear seat of the patrol vehicle, 

without handcuffs, without being searched, and was permitted to put on his own 

seatbelt.

64. WAITE, SIMS, and/or MALGRAT then locked HMM in the back of 

the patrol vehicle.

65. WAITE and/or SIMS then transported HMM to the adult jail for 

processing.

66. A true and correct copy of a video recording of the incident was 

attached at Exhibit 1 to the Complaint (Doc. 1) and is incorporated herein by 

reference.

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67. Pursuant to FED.R.CIV.P. 11(b)(3), the following factual contentions 

will likely have evidentiary support after a reasonable opportunity for further 

investigation or discovery:

a. CITY adopted and implemented policies and procedures that permitted 

the aforementioned conduct;

b. In the alternative, CITY failed to enforce their policies and procedures 

that would have prevented the aforementioned conduct;

c. CITY did not adopt and implement, or did not enforce, policies, 

procedures and/or training that complied with industry standards regarding criminal 

 

1 The video is redacted to remove HMM’s name and to pixelate HMM’s face.

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investigation, use of force, arrest, policing within an elementary school, policing 

disabled persons, transportation of juveniles, and/or the processing of juveniles;

d. CITY did not adopt and implement, or did not enforce, policies, 

procedures and/or training that complied with the Americans with Disabilities Act 

(“ADA”), regarding the criminal investigation, use of force, arrest, policing within 

an elementary school, policing disabled persons, transportation of juveniles, and/or 

the processing of juveniles;

e. CITY discovered the above conduct from school records, written 

reports, court documents, WAITE, SIMS, MALGRAT, and/or MALGRAT’S body 

camera video;

f. CITY did not conduct an internal investigation of the incident;

g. CITY did not discipline WAITE, SIMS, and/or MALGRAT; and

h. CITY did not retrain WAITE, SIMS, and/or MALGRAT.

68. As a direct result of the Defendants’ conduct, HMM suffered a 

psychological injury that manifested itself physically, i.e., loss of breath, hives, 

stomach aches, headaches, insomnia, nightmares, and refusal to sleep alone.

COUNT I

Plaintiff v. Defendants Herin, Sheer, Henriquez, and Malgrat

Fourteenth Amendment (State Created Danger)

Pursuant to 42 U.S.C. § 1983

69. Paragraphs 1-68 are incorporated herein by reference.

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70. HERIN and SHEER were school officials who observed the 

aforementioned events and failed to intervene to stop any of them.

71. HERIN and SHEER, as school officials, HENRIQUEZ, as a teacher, 

and MALGRAT, as a school resource officer, had a special relationship with HMM 

who was a special needs student in the school.

72. Specifically, during the school day, they served in loco parentis to 

HMM.

73. As a result of this special relationship, HERIN, SHEER, HENRIQUEZ 

and MALGRAT had a duty to protect HMM from injury.

74. Despite this duty, HERIN, SHEER, HENRIQUEZ and MALGRAT 

increased the risk that HMM would suffer injury when they caused WAITE and 

SIMS to be summoned to the school for the unlawful purpose of teaching HMM a 

lesson and trying to scare HMM into “behaving” in the future.

75. As a direct and proximate result of the Defendants’ conduct, HMM 

suffered and will continue to suffer embarrassment, humiliation, and psychological 

injury that manifested itself physically, some or all of which may be permanent.

76. As a direct and proximate result of the Defendants’ conduct and the 

prosecution of this civil litigation, Plaintiff has incurred and will incur attorneys’ 

fees and litigation costs.

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COUNT II

Plaintiff v. Defendants Waite, Sims, and Malgrat

Fourth Amendment (Excessive Force)

Pursuant to 42 U.S.C. § 1983

77. Paragraphs 1-68 are incorporated herein by reference.

78. The Fourth Amendment protects citizens from unreasonable searches 

and seizures, which “encompasses the right to be free from excessive force during 

the course of a criminal apprehension.” Oliver v. Fiorino, 586 F.3d 898, 905 (11th 

Cir. 2009). 

79. Courts analyze claims that officers have violated that right using the 

Fourth Amendment’s “objective-reasonableness standard.” Patel v. City of Madison, 

Ala., 959 F.3d 1330, 1338 (11th Cir. 2020). 

80. That standard requires courts to consider whether the officers' conduct 

was “objectively reasonable in light of the facts confronting” them. Id. (quotation 

omitted).

81. Whether an officer used a reasonable amount of force depends on “(1) 

the severity of the crime; (2) whether the individual posed an immediate threat to the 

safety of the officers or others; and (3) whether the individual actively resisted arrest 

or attempted to evade arrest by flight.” Patel, 959 F.3d at 1339 (alteration and 

quotation marks omitted) (quoting Graham v. Connor, 490 U.S. 386, 396 (1989)).

82. The Eleventh Circuit has also considered “(4) the need for force to be 

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applied; (5) the amount of force applied in light of the nature of the need; and (6) the 

severity of the injury.” Id.

83. An objectively reasonable police officer, i.e., a police officer acting in 

accordance with state and federal law, local and national training standards, and the 

Key West Police Department’s policies and procedures, would have known that (a) 

seizing HMM, (b) using force against HMM, (c) restricting HMM’S movement, and 

(d) causing HMM’S continued detention, would violate clearly established law.

84. Specifically, an objectively reasonable police officer would know that 

handcuffing an 8 year old boy, who was only approximately 3 feet 6 inches tall, 64

pounds, who posed no threat to himself or others, and who did not present as a flight 

risk, for the purpose of teaching him a lesson, violated clearly established law and 

violated the Fourth Amendment as a matter of law. See Gray ex rel Alexander v. 

Bostic, 458 F.3d 1295 (11th Cir. 2006).

85. As a direct and proximate result of the Defendants’ conduct, HMM 

suffered and will continue to suffer embarrassment, humiliation, and psychological 

injury that manifested itself physically, some or all of which may be permanent.

86. As a direct and proximate result of the Defendants’ conduct and the 

prosecution of this civil litigation, Plaintiff has incurred and will incur attorneys’ 

fees and litigation costs.

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COUNT III

Plaintiff v. Defendants Herin, Sheer, Henriquez, Waite, Sims, and Malgrat

Fourth Amendment (Duty to Intervene)

Pursuant to 42 U.S.C. § 1983

87. Paragraphs 1-68 are incorporated herein by reference.

88. A government official may be liable for the excessive force or other 

unlawful conduct of another if s/he fails to intervene to stop or prevent the 

constitutional violation. See, e.g., Priester v. City of Riviera Beach, Fla., 208 F.3d 

919 (11th Cir. 2000).

89. HERIN, SHEER, HENRIQUEZ, WAITE, SIMS, and MALGRAT each 

had a duty to intervene to prevent some or all of their co-defendants from engaging 

in unlawful conduct.

90. HERIN, SHEER, HENRIQUEZ, WAITE, SIMS, and MALGRAT each 

had a duty to intervene to prevent some or all of their co-defendants from causing 

HMM to unlawfully suffer injury.

91. HERIN, SHEER, HENRIQUEZ, WAITE, SIMS, and MALGRAT each 

had a meaningful and appreciable opportunity to intervene to prevent some or all of 

their co-defendants from engaging in some or all of the aforementioned conduct but 

failed or refused to do so.

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92. As a direct and proximate result of the Defendants’ conduct, HMM 

suffered and will continue to suffer embarrassment, humiliation, and psychological 

injury that manifested itself physically, some or all of which may be permanent.

93. As a direct and proximate result of the Defendants’ conduct and the 

prosecution of this civil litigation, Plaintiff has incurred and will incur attorneys’ 

fees and litigation costs.

COUNT IV

Plaintiff v. Defendant City

Americans with Disabilities Act

94. Paragraphs 1-68 are incorporated herein by reference.

95. Title II of the Americans with Disabilities Act (“ADA”) applies to state 

and local government entities, and, in subtitle A, protects qualified individuals with 

disabilities from discrimination on the basis of disability in services, programs, and 

activities provided by state and local government entities. 

96. Title II extends the prohibition on discrimination established by section 

504 of the Rehabilitation Act of 1973, as amended, 29 U.S.C. 794, to all activities 

of state and local governments regardless of whether these entities receive Federal 

financial assistance.

97. The CITY, through its agents and employees, knew that HMM suffered 

from a qualifying disability.

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98. The CITY, through its agents and employees, assumed a duty of care 

over HMM.

99. The CITY failed to provide proper policy or training to its agents and 

employees who they assigned the duty of providing care, custody, and control, over 

minor disabled students like HMM.

100. The CITY assigned or otherwise permitted its agents and employees, 

who were not properly trained or supervised regarding HMM’s disabilities, to 

provide care, custody, and control, over HMM.

101. The CITY, through its agents and employees, failed to accommodate 

HMM’s disability.

102. The CITY, through its agents and employees, denied HMM equal 

access to education for a part of the school day because of his disability.

103. As a direct and proximate result of the Defendants’ conduct, HMM 

suffered and will continue to suffer embarrassment, humiliation, and psychological 

injury that manifested itself physically, some or all of which may be permanent.

104. As a direct and proximate result of the Defendants’ conduct and the 

prosecution of this civil litigation, Plaintiff has incurred and will incur attorneys’ 

fees and litigation costs.

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COUNT V

Plaintiff v. Defendant City

Fourth and Fourteenth Amendments—Municipal Liability

Pursuant to 42 U.S.C. § 1983

105. Paragraphs 1-68 are incorporated herein by reference.

106. “Local governing bodies . . . can be sued directly under § 1983 for 

monetary, declaratory, or injunctive relief where . . . the action that is alleged to be 

unconstitutional implements or executes a policy statement, ordinance, regulation, 

or decision officially adopted and promulgated by that body’s officers.” Monell v. 

Dep’t of Soc. Servs., 436 U.S. 658, 690 (1978).

107. In addition, a failure to train may give rise to municipal liability if the 

failure to train amounts to “deliberate indifference to the rights of persons with 

whom the [untrained employees] come into contact.” Canton v. Harris, 489 U.S. 

378, 388 (1989).

108. CITY knowingly failed to maintain policies, practices, and training that 

met the minimum standards in the industry.

109. Merely sending a police officer to the academy does not satisfy training 

obligations.

110. Rather, the CITY remained responsible for ensuring that its police 

officers were properly trained, remained properly trained, and acted in accordance 

with said training.

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111. As discussed herein, CITY maintained policies, practices, and customs, 

which were the moving force that resulted in HMM’S constitutional rights being 

violated.

112. In the alternative, CITY failed to implement proper policies and 

training, as discussed herein, which was the moving force that resulted in HMM’S

constitutional rights being violated.

113. As a direct and proximate result of the Defendants’ conduct, HMM 

suffered and will continue to suffer embarrassment, humiliation, and psychological 

injury that manifested itself physically, some or all of which may be permanent.

114. As a direct and proximate result of the Defendants’ conduct and the 

prosecution of this civil litigation, Plaintiff has incurred and will incur attorneys’ 

fees and litigation costs.

WHEREFORE, Plaintiff respectfully requests that judgment be entered in 

her favor as follows: 

A. Declaratory Judgment: Providing that the Defendants’ individual and 

collective conduct violated HMM’S Federal Constitutional rights;

B. Compensatory Damages: Including, but not limited to, the monetary 

value associated with the following: violations of legal rights, emotional distress, 

emotional injury, loss of liberty, embarrassment, and loss of reputation;

C. Punitive damages as permitted by law;

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D. Equitable Relief: A written admission of the allegations stated in the 

Complaint, an in-person oral apology, and a written admission and apology on the 

CITY’S official letterhead;

E. Attorney’s Fees and Costs; and

F. Discretionary Damages and Relief: Such other financial or equitable 

relief that the Court deems reasonable and just.

Jury Trial Demand

Plaintiff respectfully requests a trial by jury on all claims/issues in this matter 

that may be tried to a jury.

Respectfully Submitted,

s/ Devon M. Jacob

DEVON M. JACOB, ESQUIRE Date: December 4, 2020

PA Bar ID: 89182

Email: djacob@jacoblitigation.com

JACOB LITIGATION, INC.

P.O. Box 837, Mechanicsburg, Pa. 17055-0837

Telephone: (717) 796-7733

Counsel for Plaintiff (Pro Hac Vice)

s/ Benjamin L. Crump Date: December 4, 2020

BENJAMIN L. CRUMP, ESQUIRE

Bar ID: 0072583

Email: ben@bencrump.com

BEN CRUMP LAW, PLLC

122 S. Calhoun, Street, Tallahassee, FL 32301

Telephone: (844) 638-1822

Counsel for Plaintiff

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IN THE UNITED STATES DISTRICT COURT

FOR THE SOUTHERN DISTRICT OF FLORIDA (Key West)

BIANCA N. DIGENNARO, as the Civil Action No.: 4:20-cv-10094

legal guardian of HMM, a minor,

JURY TRIAL DEMANDED

Plaintiff, CIVIL ACTION – LAW

v. Chief Judge: K. Michael Moore

MICHAEL L. MALGRAT, et al.,

Defendants.

CERTIFICATE OF SERVICE

I, Devon M. Jacob, Esquire, hereby certify that on the below referenced date, 

I caused a true and correct copy of this document to be served, via ECF, on all 

counsel of record.

Respectfully Submitted,

s/ Devon M. Jacob Date: December 4, 2020

DEVON M. JACOB, ESQUIRE

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