Gregory Session v. H.D. Gator DeLoach, in his official capacity as Sheriff, Putnam County, Florida

CourtDistrict Court, M.D. Florida
DecidedDecember 30, 2025
Docket3:23-cv-00170
StatusUnknown

This text of Gregory Session v. H.D. Gator DeLoach, in his official capacity as Sheriff, Putnam County, Florida (Gregory Session v. H.D. Gator DeLoach, in his official capacity as Sheriff, Putnam County, Florida) is published on Counsel Stack Legal Research, covering District Court, M.D. Florida primary law. Counsel Stack provides free access to over 12 million legal documents including statutes, case law, regulations, and constitutions.

Bluebook
Gregory Session v. H.D. Gator DeLoach, in his official capacity as Sheriff, Putnam County, Florida, (M.D. Fla. 2025).

Opinion

UNITED STATES DISTRICT COURT MIDDLE DISTRICT OF FLORIDA JACKSONVILLE DIVISION

GREGORY SESSION,

Plaintiff, Case No. 3:23-cv-170-TJC-PDB v.

H.D. GATOR DELOACH, in his official capacity as Sheriff, Putnam County, Florida,

Defendant.

ORDER THIS CASE is before the Court on Defendant’s Dispositive Motion for Summary Judgment, which has been fully briefed. Docs. 76, 85, and 90. Plaintiff Gregory Session has sued his former employer, Sheriff “Gator” DeLoach, alleging his termination was improper and violated various statutes prohibiting race discrimination, disability discrimination, and his rights to leave.1

1 The operative complaint has seven remaining claims. Doc. 7. Counts I, III, and V allege race discrimination under Title VII, 42 U.S.C. § 1981, and the Florida Civil Rights Act, respectively. Count VII is for disability discrimination (failure to accommodate) under the Americans with Disabilities Act and is limited to Session’s heart condition. Doc. 37. Count VIII is for ADA retaliation. Count IX is for Family and Medical Leave Act interference. Count X is for FMLA retaliation. Counts II, IV, and VI, for retaliation, have been dismissed. Doc. 37. Count XI, alleging workers compensation retaliation, was severed and remanded. Doc. 19. Session’s opposition to summary judgment claims he was not paid from October 12, 2021, through November 8, 2021 (involving pay for time worked and administrative leave), but he has not made a separate claim I. BACKGROUND2 A. Employment Overview

Session, who is Black, worked in corrections for the Sheriff from 1986, until his retirement in 2011.3 Doc. 75-1 at 17–18, 31. His last position was lieutenant. Id. at 17. The Sheriff rehired Session in March 2013, and terminated Session in November 2021. Doc. 75-1 at 64. In his second employment term,

Session was always a corrections deputy. See Doc. 75-1 at 17. B. Prior Discipline and Probation (May-June 2021) In May 2021, a kitchen employee complained Session engaged in bullying and threatening behavior. See Doc. 75-1 at 262–69. Session claimed the incident

was made up and that he was confused with another Black officer who admitted to bullying. Doc. 75-1 at 82–84. Even so, Session testified that someone in the kitchen was “badgering” him and his response included cussing. Doc. 75-1 at

for the unpaid time nor argued how this supports any remaining claim. Compare Doc. 85 at 15–16 with Doc. 7. 2 To oppose summary judgment, Session submitted l76 exhibits, totaling almost 5,000 pages. The Sheriff has challenged much of the evidence and the parties have agreed to exclude some items, but the Sheriff continues to dispute others. See Doc. 93. These disputed items include all remaining exhibits that are part of Docs. 82 and 83, except Docs. 83-32 and 83-33, the jail audit report and related documentation. However, for purposes of the motion for summary judgment, the Court has considered all of Plaintiff’s evidence. 3 The Court generally refers to the Defendant as Sheriff, because he has been sued in his official capacity. DeLoach became sheriff in 2017, but he was not sheriff when Session was rehired. 93–94. John Zagar investigated, including interviews with six witnesses and Session. Doc. 75-1 at 262–68. The investigation sustained the alleged violations.

Doc. 75-1 at 269. Session was disciplined in June 2021, including twelve months of probation. Id. Session appealed the discipline but there was no change. Docs. 80-29, 80-33. C. Miscount Incident, Investigation, and Termination (September- November 2021)

The jail regularly conducts inmate counts, including counts every six hours. If the initial count is incorrect (“does not clear”), there is a recount. See Doc. 75-1 at 107–08, 131. If the recount is incorrect, then a master count is done. See id. at 98, 110. A master count involves full lockdown, and a physical count of inmates comparing armbands to a roster list. Id. at 98. If the master count is

incorrect the jail will report a missing inmate. Id. at 112–13. On September 14, 2021, Session, Terrance Haynes, and Isaiah Decent were on duty together. Session and Haynes are Black, while Decent is mixed race and light skinned. Id. at 48, 103; Doc. 82-29 at 67. On this day, Decent did

both the count and recount incorrectly. Doc. 75-1 at 36, 102, 107–09. Session did the master count and it cleared. Id. at 110. Lieutenant Steven Breckenridge, white, was also on duty that day. See Doc. 75-1 at 78. Because of recurring problems with inmate counts,

Breckenridge decided to review video. His review identified problems with the count and recount and multiple other policy violations by all three officers. Id. The same day, Breckenridge requested all three officers be investigated.4 Id.

On October 15, 2021, Session made a written complaint about a “total hostile working environment” and “being scrutinized.” Doc. 80-37. The complaint does not mention race and does not provide any examples of a hostile work environment or how he was scrutinized.5 Later that day, Session was

notified of the investigation into the miscount and other issues.6 Doc. 81-2 ¶¶ 42, 44; Doc. 75-1 at 272. Zagar did three investigations, one for each officer. Docs. 80-7, 82-2; see Doc. 80-71. For Session, the investigation addressed twelve alleged violations

that Session, Decent, and Haynes “knowingly neglected their duties regarding searching inmates, allowing inmates to travel within the jail without supervision and failing to accurately perform mandatory head counts.” Doc. 80- 7. Zagar reviewed video and interviewed Haynes and Decent. Id. Zagar tried to

interview Session twice, but Session was out of work both days due to an injury.

4 Breckenridge’s request was addressed to Captain Clayton Silva and approved by Colonel Joseph Wells. See Doc. 75-1 at 115, 270, 273. 5 Per Session, Breckenridge assigned himself to cover staff shortages on Session’s shift to target Session. Doc. 75-1 at 37. 6 A memo to Session on October 20, 2021, stated his complaint was “received immediately following” the notice that he was the subject of an administrative investigation, and the complaint would therefore be part of the investigation file. Doc. 80-38. Doc. 75-1 at 138–39. Zagar also interviewed Lieutenant Kathy Yoder “who explained proper jail policy and procedures and identified violations in the []

videos.” Doc. 80-7 at 4. Zagar’s investigation report was issued October 27, 2021, and sustained all the alleged violations. Id. The Sheriff has final authority for discipline, but discipline recommendations are reviewed by multiple levels and are separate from the

investigation. See Doc. 75-16 at 41; Doc. 80-37. For Session, termination was recommended and approved by all supervisory levels on October 27, 2021, with the Sheriff’s approval on October 28, 2021. Doc. 80-39. The Sheriff notified Session his employment was terminated and of his right to a name clearing

hearing the same day he approved the termination.7 Doc. 80-8; see Doc. 75-15 at 22. The next to last approval was from Colonel Joseph Wells, who recommended termination because Session was already on probation.8 Doc. 75- 15 at 62–63; Doc. 80-39.

7 Alleged violations were also sustained for Decent and Haynes. Doc. 82- 3; see Doc. 80-71. Decent had no disciplinary history and Haynes had not been disciplined since being reemployed in 2018. For Decent, the Sheriff decreased the recommended discipline to a written reprimand, 12-hour suspension (down from 24 hours), and one year of probation. Doc. 80-71. For Haynes, the Sheriff increased the recommended discipline to termination (instead of written reprimand, 36-hour suspension, and one year probation). Doc. 82-10. Haynes has also sued alleging his termination was discriminatory.

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Gregory Session v. H.D. Gator DeLoach, in his official capacity as Sheriff, Putnam County, Florida, Counsel Stack Legal Research, https://law.counselstack.com/opinion/gregory-session-v-hd-gator-deloach-in-his-official-capacity-as-sheriff-flmd-2025.