UNITED STATES DISTRICT COURT 

SOUTHERN DISTRICT OF FLORIDA 

MIAMI DIVISION

CASE NO. 1:20-cv-21707-MARTINEZ/BECERRA

RAYMOND JAMES FINANCIAL, INC.,

Plaintiff,

vs.

FEDERAL INSURANCE COMPANY; 

TRAVELERS CASUALTY AND 

SURETY COMPANY OF AMERICA;

GREAT AMERICAN INSURANCE COMPANY; 

BEAZLEY INSURANCE COMPANY, INC.; and 

ST. PAUL MERCURY INSURANCE COMPANY,

Defendants.

/

PLAINTIFF’S MOTION TO COMPEL DOCUMENTS AND ASSOCIATED 

TESTIMONY FROM DEFENDANTS AND SUPPORTING MEMORANDUM OF LAW

Plaintiff, Raymond James Financial, Inc. (“Raymond James”), by and through undersigned 

counsel and pursuant to Rule 37 of the Federal Rules of Civil Procedure and this Court’s Orders 

at ECF Nos. 71, 76, 79, and 144, moves for the entry of an Order compelling Defendants Federal 

Insurance Company (“Federal”), Travelers Casualty and Surety Company of America 

(“Travelers”), Great American Insurance Company (“Great American”), Beazley Insurance 

Company, Inc. (“Beazley”), and St. Paul Mercury Insurance Company (“St. Paul”) (collectively, 

“Defendants” or “Insurers”) to produce documents that pre-date the Insurers’ denial of coverage

and which were improperly withheld on the basis of the attorney-client privilege and/or the workproduct doctrine and supply associated deposition testimony. In support thereof, Raymond James

submits the following memorandum of law.

I. INTRODUCTION

Nearly all of the Defendants agree that they have certain non-delegable obligations pertinent 

to handling insurance claims submitted by their policyholders like Raymond James. These 

obligations include the following:

1. An insurance company must adopt and implement standards for the proper 

investigation of claims;

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2. An insurance company must disclose to its insured all benefits, coverages and time 

limits that apply to a specific claim;

3. An insurance company must treat its policyholder’s interests with equal regard as 

its own; in fact, a company must give its policyholder the benefit of the doubt when 

considering the facts in a claim investigation;

4. An insurance company may not misrepresent pertinent facts or policy provisions 

relating to coverages;

5. An insurance company must conduct a full, fair and prompt investigation of the 

claim at its own expense;

6. An insurance company must fully, fairly and promptly evaluate and adjust the 

claim; and

7. An insurance company may not deny a claim or any part of a claim based upon 

insufficient information, speculation or biased information, and must have 

conducted a reasonable investigation based on available information.

Travelers, Beazley, and Great American agreed to the above-referenced industry 

standards.0 F

1 When asked about these non-delegable duties, only Federal’s corporate representative 

refused to answer on the advice of its legal counsel, Scott Schmookler, Esq., that the information 

was “privileged” (Deposition of Ken West [ECF No. 126-2] (“West Dep.”) at 31:6-33:7, 33:10-

14, 33:19-20, 34:2-9, 34:16-17). Mr. West did testify that state guidelines would generally apply,

though he could not articulate those guidelines for Florida, despite the subject policy being a 

Florida issued insurance policy. (Id. at pp. 36:11-19, 37:11-14, 37:2-4, 37:11-14, 37:16-19, 37:25-

38:1, 40:8-12, 40:19-22, 44:3-5, 44:11-19, 44:22-45:1, 45:5). Moreover, Mr. West refused to 

answer questions about the type of information that Mr. Schmookler sought in connection with the 

claim. (Id. at pp. 149:7-17, 149:19-21, 149:23-150:19). The Insurers, with the exception of 

 1 Deposition of Matthew Kalin [ECF No. 126-3] (“Kalin Dep.”) at pp. 35:6-8, 35:16-18, 36:6-11, 

36:13-18, 36:21-22, 36:24-37:2, 37:4-8, 37:10-14, 37:16-19, 37:21-38:2, 38:4-16, 39:2-6, 39:8-15, 

39:17-20, 39:22-40:5, 40:7-13, 40:15-19, 40:21-22, 40:24-41:1, 41:3-8, 41:13-15, 41:23-42:1, 

42:3-4, 42:11-16, 42:18-43:2, 43:6-10, 43:12-17, 45:3-6, 45:8-10, 45:12-15, 45:18-22, 45:24-25, 

46:2-4, 46:6-11, 46:14-21, 46:23-47:2, 47:4-8; Deposition of Antonio Trotta [ECF No. 126-4] 

(“Trotta Dep.”), at pp. 38:11-17, 38:24:-39:4, 39:16-20, 40:7, 40:9-11, 40:15-17, 40:19, 40:21-24, 

41:1, 41:19-23, 42:142:11-14, 42:16-17, 42:19-23, 42:25-43:4, 43:6-9, 43:12-13, 43:15-18, 43:12-

13, 46:13-15, 46:17; Deposition of Tracey Archbold [ECF No. 126-3] (“Archbold Dep.”) at pp. 

26:6-14, 27:10-21, 27:23-24; 28:11-19, 28:25-29:13, 29:23-30:3, 30:7-10, 30:22-32:3, 32:5-

33:17, 33:19-34:17).

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Federal’s representative who refused to answer on the advice of counsel, also agreed that the duty 

to undertake a good faith claim investigation continues even after litigation with the policyholder 

incepts (West Dep. at 49:15-18, 49:24-25; Kalin Dep. at 41:17-22; Trotta Dep. at 41:3-4, 41:6-7, 

41:9-11, 41:15-17; Archbold Dep. at 30:7-10). 

The evidence shows, however, that none of the insurance carriers investigated or evaluated

Raymond James’ claim. Instead, Defendants relied upon lead counsel for Federal (Scott 

Schmookler, Esq.) to conduct the claim investigation. But, when asked at deposition about 

information relating to the claim investigation, including the substance of any relevant factual 

information, Defendants all asserted the attorney-client privilege and refused to disclose routine 

claim communications long preceding the denial of Raymond James’ claim on April 20, 2020.

Under Florida law, the attorney-client privilege does not shield from disclosure 

communications with attorneys performing claims-handling functions or investigating insurance 

claims. See, e.g., Seacoast 5151 Condo. Ass’n v. Great Am. Ins. Co. of New York, No. 17-23820-

CIV, 2018 WL 6653342, at *3-4 (S.D. Fla. Sept. 15, 2018), report and recommendation adopted, 

No. 17-23820-CIV, 2018 WL 6653071 (determining that documents reflecting communications 

with counsel prior to decision to deny coverage were not protected by the attorney-client privilege); 

The Atriums of Palm Beach Condo. Ass’n, Inc. v. QBE Ins. Co., 2009 WL 10667478 (S.D. Fla 

June 17, 2009).

Accordingly, Raymond James is entitled to the production of all documents and 

communications on the Defendants’ Privilege Logs1 F

2 reflecting the Insurers’ statutorily required 

claim investigation which were created or received prior to denying coverage on April 20, 2020, 

answers to questions relating to those communications that the Insurers’ corporate representatives 

refused to answer on the basis of attorney client and/or work product privilege, and the “market” 

communications between the Insurers for the period from December 19, 2019 to April 20, 2020.2F

3

II. BACKGROUND

This action arises from Defendants’ failure to indemnify Raymond James for covered 

 2 The Privilege Logs are attached hereto as Composite Exhibit A. Raymond James seeks only the 

highlighted communications dated prior to April 20, 2020 relating to the investigation of the claim 

and the “market” communications from December 19, 2020 to April 20, 2020.

3 As set forth below, the Insurers’ agreed to produce these “market” communications prior to 

December 19, 2019. The Insurers assert that the “market” communications between December 19, 

2019 and April 20, 2020 are protected by the attorney-client and/or work product privilege. 

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losses under a series of Financial Institution Bonds (the “Bonds”) that Raymond James purchased 

from the Defendants providing a total of $60 million in “single loss” employee fidelity coverage. 

Raymond James suffered a covered loss under the Bonds arising directly from dishonest and 

fraudulent acts committed by a Raymond James employee, Joel Burstein, in connection with the 

purchase, improvement and expansion of the Jay Peak Resort in Jay Peak, Vermont, and the Burke 

Mountain Resort in East Burke, Vermont, by Burstein’s former father-in-law Ariel Quiros. As part 

of their scheme, Burstein and Quiros, with the intent to financially benefit themselves and entities 

operated and controlled by Quiros and others, converted and misappropriated many millions of 

dollars in EB-5 investor funds from limited partnership accounts held by Raymond James. 

Upon discovery of the scheme, the SEC initiated litigation against Quiros which resulted 

in the appointment of a Receiver for the Jay Peak limited partnerships and related entitles (the 

“SEC Receiver”). Soon thereafter, numerous lawsuits were filed against Raymond James and 

Burstein, including an action by the SEC Receiver and a consolidated class action lawsuit by 

individual investors who were seeking to recover, among other damages, the funds held by 

Raymond James that had been misappropriated by Burstein and Quiros. After months of 

confidential negotiations, Raymond James agreed to settle with the SEC Receiver for the payment 

of $150 million, at least $78 million of which was for the limited partnerships in order to repay 

investors whose investment principal was both held at Raymond James and for which Raymond 

James is legally liable as result of Burstein and Quiros’ misconduct.

As a result of the lawsuits, Raymond James first “discovered” a loss under the Bonds and 

timely reported a claim under the Bonds to the Defendants in May of 2016. It then, as requested 

by Defendants, timely submitted a proof of loss on February 27, 2018. Thereafter, Raymond James 

voluntarily provided voluminous documentation (in excess of 150,000 pages) to Defendants to 

support Raymond James’ covered loss. After a lengthy two-plus year “investigation,” apparently 

conducted entirely through outside counsel, on April 20, 2020, Federal, through this same counsel,

and as the primary insurer in a follow form tower, sent Raymond James a 28-page letter detailing 

the results of Federal’s investigation and denying coverage. Soon thereafter, the other Insurers sent 

similar denial letters, all incorporating Federal’s denial letter. 

Raymond James then brought this action, asserting claims for breach of contract and 

declaratory relief, and seeking to recover the $60 million in insurance coverage Raymond James 

purchased from Defendants to cover for the very type of employee fraud and dishonesty committed 

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by Burstein. The Primary Bond grants coverage for “Loss resulting directly from dishonest or 

fraudulent acts committed by an Employee, acting alone or in collusion with others, with the intent: 

(a) To cause the Insured to sustain such loss, or (b) To obtain financial benefit for the Employee, 

or another person or entity.” The Primary Bond applies to “loss of Property (1) owned by the 

Insured, (2) held by the Insured in any capacity, or (3) for which the Insured is legally liable,” 

including money. Each of the excess bonds provides coverage on a follow-form basis 

incorporating the terms of the Primary Bond. Defendants bear the burden of proving any 

exclusions to coverage. See, e.g., U.S. Concrete Pipe Co. v. Bould, 437 So. 2d 1061, 1065 (Fla. 

1983) (insurer bears the burden of proving the applicability of any exclusions to coverage).

Raymond James served Federal with a First Request for Production on June 28, 2020. On 

September 10, 2020, Federal served its objections and responses thereto. 3F

4 Federal subsequently 

produced four privilege logs between September 16 and 18, 2020, and documents responsive to 

the First Request for Production on September 22, 2020. In response to Request No. 2, seeking the 

contents of Federal’s claim file, Federal produced very limited documents and otherwise withheld 

from production numerous documents on the basis of the attorney-client privilege and/or work 

product doctrine – many of which pre-date Federal’s denial of coverage. The other Defendants 

similarly withheld from production numerous claim file documents which pre-date the denial of 

coverage. After reviewing the portions of the claim file Federal produced, along with Federal’s 

privilege logs, Raymond James conferred with counsel for Federal (and the other Insurers) on 

numerous occasions via telephone, email and correspondence to address, among other issues, the 

fact that Raymond James believed Federal and the other Insurers were improperly withholding 

from production documents that are not privileged. 

Following telephonic conferences on October 14 and October 19, and as part of the agreed 

upon conferral process, Raymond James sent a detailed letter to Federal on October 20, 2020, 

providing Federal with Raymond James’ analysis of the applicable law on privilege and its reasons 

for disputing Federal’s claims of privilege. In that letter, Raymond James made clear that, while it 

was not disputing the attorney-client privilege with respect to certain documents and 

communications where counsel was providing legal advice concerning the parties’ tolling 

agreement or confidentiality agreements, Raymond James was seeking the production of 

 4 A copy of Federal Insurance Company’s Objections and Responses to Raymond James Financial, 

Inc.’s First Request for Production is attached hereto as Exhibit “B.”

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documents and communications between Federal and its counsel relating to the claim 

investigation, which were created or received prior to Federal’s April 20, 2020 denial of coverage.

In response to that letter, on October 22, 2020, Federal sent Raymond James two revised 

privilege logs: one privilege log covered communications between Federal and its counsel and the 

other covered “market” communications between the various insurance carriers. After further 

discussions, the parties agreed that Federal and the other carriers would produce to Raymond 

James all “market” communications prior to January 1, 2020, without prejudice to Raymond 

James’ right to challenge the carriers’ privilege assertions on the remaining documents – namely, 

the market communications after December 31, 2019 (i.e., for the approximately 3.5 months before 

the denial of coverage) and all documents and communications reflecting the carriers’ statutorily 

required claim investigation which were created or received prior to denying coverage on April 

20, 2020. 

Consistent with then Magistrate Judge O’Sullivan’s discovery procedures, on January 28, 

2021, the parties held a discovery hearing on Raymond James’ challenges to Federal’s and 

Travelers’ assertions of the attorney-client and/or work product privileges with respect to certain 

documents on their respective privilege logs. Following the hearing, on January 29, 2021, 

Magistrate Judge O’Sullivan entered an Order setting a briefing schedule on the attorney-client 

and work product privilege disputes and ordering the parties to confer in an attempt to narrow the 

issues. [ECF No. 71]. Following further conferrals, and in an effort to try to resolve the dispute 

without requiring briefing and a potential in camera review of documents, the parties reached an 

agreement to defer any potential briefing until after Raymond James had taken certain of the 

Defendants’ Rule 30(b)(6) depositions. [ECF No. 76]. In accordance with the parties’ agreement, 

on March 4, 2021, Magistrate Judge O’Sullivan entered an Order deferring briefing on the 

attorney-client and work product privileges until after Raymond James took the 30(b)(6) 

depositions of Federal and Travelers. [ECF No. 79].4F

5

 

Raymond James has now taken the Rule 30(b)(6) depositions of each of the Defendants.

Those depositions confirmed that Defendants relied on outside counsel to investigate Raymond 

 5 Each of the other Defendants, Great American and Beazley, have also improperly withheld 

documents on the basis of the attorney-client privilege and/or the work-product doctrine. Via email 

dated July 2, 2021, counsel for Beazley indicated that Beazley and Great American were agreeable 

to proceeding in the manner contemplated by this Order. 

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James’ claim, and that Defendants improperly withheld from production communications where 

counsel performed solely claims-handling functions. Counsel for the deponents instructed the 

witnesses, however, not to answer certain questions concerning the investigation and evaluation 

of Raymond James’ claim based on the attorney-client privilege, even though each Defendant 

admitted that outside legal counsel conducted the claim investigation on its behalf. On August 12, 

2021, the successor Magistrate Judge Becerra entered an order establishing a briefing schedule on 

this matter. [ECF No. 144].

FEDERAL

Ken West was the Federal claim adjuster assigned to Raymond James’ claim. He admitted 

at deposition that he only spoke to Raymond James one time regarding the claim (West Dep. [ECF 

No. 126-2] at 127:16-18:9). Federal retained Scott Schmookler, Esq., counsel of record in this 

litigation, on March 19, 2018 – less than one month after Raymond James submitted its proof of 

loss and more than two years before Federal denied coverage (Id. at 134:15-135:13). Mr. West’s 

testimony makes it abundantly clear that Federal delegated its entire claim investigation to Mr. 

Schmookler as of March 19, 2018.5F

6 

Q What, if anything did you do, Mr. West, to investigate Raymond James’ claim after 

March 19, 2019 [sic]?

A The date we retained counsel:

Q Correct

A I didn’t - - we didn’t - - I didn’t - - once that – I’m sorry, once we retained counsel, 

all communications would go - - were going through counsel.

(Id. at p. 139:12-20).

Mr. West admitted that he never reached out to anybody at Raymond James after March 

19, 2018, and that all communications after this date were through Mr. Schmookler, though he 

refused to testify as to what he asked Mr. Schmookler to do and what information he requested 

Mr. Schmookler seek from Raymond James as part of the claim investigation.

Q Well, is it fair to say, Mr. West, in the investigation of the claim done by you on 

behalf of Chubb following March 19 of 2018, you did not reach out directly to 

anybody at Raymond James, correct.

A I don’t recall reaching out to anybody after March 19th of 2018, to anybody at 

 6 Despite the testimony by Mr. West that Federal “must conduct a full, fair, and prompt 

investigation of its policyholder’s claim at its own expense” (West Dep. [ECF 126-2] at 46:13-17; 

46:23-25; 47:10-13; 47:19-23; 48:14-17; 48:19-23), Mr. West somehow could not articulate, 

after 28 years of experience in claims handling, any specifics. (Id. at pp. 52:12-16; 52:22-25, 53:3-

5, 53:11-12).

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Raymond James.

(Id. at p. 140:1-7).

Q Do you see anything in the claim file that’s sitting in front of you that shows you 

[or] anybody else at Chubb directly requesting any information from Raymond 

James after March 19 of 2018? If you need to, you can look through the whole 

thing.

A It appears after reviewing the claim file after the date we retained Scott Schmookler 

all requests for information appear to have been made, unless I missed something 

between Scott Schmookler and your firm.

(Id. at 143:14-18; 143:22-144:2).

Mr. West also refused to answer direct questions about the scope of the claim investigation 

it authorized outside counsel to conduct: 

Q My question is prior to litigation and throughout the pendency of the claim 

investigation, after you hired Mr. Schmookler’s firm on March 19, 2018, what did 

you ask them to do?

MR. SCHMOOKLER: Object to the form. That calls for attorney-client 

communication. Do not answer, Ken.

A I am not answering the question because it seeks disclosure of attorney-client 

privileged information.

(Id. at pp. 152:18-153:6)

Despite having no communication with Raymond James for over two years, Mr. West 

authorized Mr. Schmookler to deny the claim (Id. at p. 174:17-20). Federal, through Mr. 

Schmookler, issued its claim denial letter to Raymond James’ on April 20, 2020. (Id. at p. 174:5-

8). Mr. West did not draft any part of the claim denial letter (Id. at p. 175:2-6). Although he may 

have made changes to the draft denial letter, he did not keep those changes in the claim file. (Id. at 

p. 175:7-18).

Mr. West’s inability at his deposition to correct a fundamental misunderstanding of a key

fact in his case further demonstrates that any claim investigation was conducted by outside counsel.

Specifically, in its Verified Interrogatories (ECF No. 122-1), Federal misstates that a margin loan 

was used to purchase the Jay Peak Resort. This statement is inaccurate. Direct EB-5 investor funds 

were improperly used to purchase the resort. Had Federal conducted a good faith claim 

investigation, as opposed to paying outside counsel with ethical obligations to zealously represent 

the carrier to conduct it, Mr. West undoubtedly would have been aware of this key fact at the time 

of his deposition. Worse, Mr. West admitted that he did not review any of the deposition testimony 

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taken in this lawsuit prior to testifying. (West Dep. at 181:15-23). Mr. West further refused to say 

whether interrogatory answers seeking the factual basis for certain contentions raised by Federal 

were still correct because it would require the disclosure of attorney-client privileged information. 

(Id. at p. 184:5-10). He also refused to answer questions regarding communications with Federal’s 

counsel during the pendency of the claim. See, e.g., (Id. at pp. 137:12-138:14; 149:23-150:6-18; 

151:9-18; 152:18-153:6; 165:2-165:20).

GREAT AMERICAN

Great American’s corporate representative did not know if anyone outside of Mr. 

Schmookler’s law firm investigated the claim on behalf of Federal (Archbold Dep. [DE-126-2] at 

101:25-102:4). Yet, Great American incorporated Federal’s denial of coverage letter (prepared by 

counsel following counsel’s investigation) as its own and issued a denial letter to Raymond James 

on April 29, 2020 (Id. at pp. 88:5-15; 89:4-11). Great American’s claim “investigation” consisted 

of coordinating with the “primary” (Federal) to address questions and the review of documents 

with “counsel’s assistance.” (Id. at 92:2-11; 92:13-14; 92:16-93:15). Great American never 

reached out to Raymond James for any additional information. (Id. at 92:16-93:17). Like Federal, 

Great American relied on counsel to investigate Raymond James’ claim, but refused to answer any 

questions with respect to communications it had with outside counsel prior to denying the claim. 

Q During the course of Great American’s claim investigation and to Raymond 

James’ claim [sic], were there communications between Great American and Mr. 

Dratch’s law firm concerning that investigation, evaluation and adjustment of 

Raymond James’claim?

MR. DRATCH: And I am going to stand on attorney-client privilege and instruct the 

witness not to answer.

Q Are you following that instruction, ma’am?

A Counsel, I will not answer that question.

(Id. at 87:5-15; see also 106:4-108:15). Like Federal, Great American also had factual inaccuracies 

in its sworn Interrogatories (Archbold Dep. at pp. 116:6-117:18). Great American’s representative 

could also not accurately testify as to how the Jay Peak resort was bought, a key fact in this case. 

Had she conducted the required investigation and not relied on counsel, she could have responded 

to questions about the claim (Id. at pp. 99:9-100:15).

BEAZLEY

Beazley also does not know who investigated the claim on behalf of Federal. (Trotta Dep.

at 120:16-17; 120:24-25; 121:5-6; 121:8, 121:10-11, 121:13-14). Beazley did not reach out to or 

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speak with anyone at Raymond James at any time during the claim investigation (Id. at pp. 75:14-

20; 98:12-99:8). Instead, Beazley relied on its outside counsel to provide advice and guidance as 

to what documents it should review during the claim investigation.(Id. at pp. 91:16-18; 91: 21-23). 

But Beazley’s corporate representative refused to answer any questions relating to 

communications with its outside counsel regarding the documents prior to the denial of the claim 

by Beazley (Id. at pp. 106:9-107:3). Incredibly, Beazley even refused to disclose what documents 

it had its counsel request from Raymond James as part of the claim investigation:

Q Do you recall – do you recall seeing communications between Beazley and its 

counsel with respect to additional records that Beazley would request as part of its 

claim investigation?

MR. KEELY I am going to object on the basis of the attorney/client privilege, and Mr.

Trotta, instruct you not to answer.

A I think I will take my counsel’s advice on that.

(Id. at pp. 84:22-85:5).

Like the other Defendants, Beazley adopted Federal’s denial letter, though it did not 

participate in the preparation of Federal’s denial letter (Id. at pp. 108:3-14; 111:8-14; 116:2-5). 

Beazley also misstated pertinent facts in its answers to Raymond James’ Interrogatories (Trotta 

Dep at 124:23-125:2, 125:14-15, 126:2-6, 126:17-20), further suggesting that this insurer did not 

conduct its own investigation.

TRAVELERS AND ST. PAUL

Travelers and St. Paul (collectively, “Travelers”) had limited communications with 

Raymond James concerning the claim, consisting of perhaps two phone calls, one conference call, 

and a few emails very early on (Kalin Dep. [DE 126-5] at pp. 81:19-82:16; 83:19-84:12). Travelers 

did not request to speak to anyone at Raymond James between the time Raymond James submitted 

its proof of loss on February 29, 2018 and the issuance of Travelers’ denial letter on April 22, 2020 

(Id. at pp. 85:19-23, 85:25-86:13). Even though Travelers’ claim representative testified that he 

reviewed documents, he did not participate in the drafting of the Federal denial letter, which 

Travelers adopted (Id. at 74:6-25). Travelers’ representative similarly refused to answer questions 

regarding the contents of Travelers’ privilege log dated prior to April 20, 2020 (Id. at 110:25-

111:6-12; 113:6-115:16). 

Based on the above, coupled with the fact that counsel authored Federal’s detailed April 

20, 2020 denial of coverage letter, it is clear that the Insurers conducted their claim investigation 

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entirely through counsel, with counsel acting as a claims investigator for the carriers.6 F

7 Indeed, 

many of the entries on Defendants’ privilege logs relate to documents and communications years 

and months before Federal denied coverage on April 20, 2020. These documents could not 

possibly have been prepared in anticipation of litigation, as opposed to the Insurers’ non-delegable 

duty to investigate, evaluate and adjust Raymond James’ claim. These documents and 

communications are relevant and presumed discoverable, regardless of whether they include 

counsel, and the Insurers cannot meet their burden to demonstrate otherwise. This Court should

accordingly overrule the Insurers’ assertions of privilege and order each Defendant to produce all 

the documents listed on its revised privilege logs that pre-date Federal’s denial of coverage on 

April 20, 2020 and the “market” communications, and order that each Insurer re-produce its 

corporate representatives to answer questions regarding the claim.7F

8

III. ARGUMENT

A. The Standards for Invoking the Attorney-Client Privilege and Work Product 

Doctrines in the Insurance Context

Where, as here, the party asserting the attorney-client privilege is a corporation, its claims 

of privilege are subject to heightened level of scrutiny “to minimize the threat of corporations

cloaking information with the attorney-client privilege in order to avoid discovery.” S. Bell Tel. 

& Tel. Co. v. Deason, 632 So. 2d 1377, 1383 (Fla. 1994). The burden of establishing the attorneyclient privilege rests on the party claiming it – here, Defendants. Id. Among other things, 

Defendants must establish that the communication would not have been made but for the 

contemplation of legal services, and that the content of the communication relates to the legal 

services being rendered. Id. “Just because a communication is between an attorney and a client 

does not mean the privilege automatically arises; the relevant question is whether an attorney was 

retained to render legal services.” St. Joe Co. v. Liberty Mut. Ins. Co., 3:05-CV-1266J- 25MCR, 

2006 WL 3391208 at *5 (M.D. Fla. Nov. 22, 2006).

Under Florida law, the attorney-client privilege does not extend to communications with 

 7 Mr. West would not answer what Federal asked Mr. Schmookler’s firm to do after it was hired 

on March 19, 2018, on the basis of the attorney-client privilege (West Dep. [126-2] at 152:18-

153:-6).

8 Or, at a minimum, Defendants should be ordered to produce these documents to the Court for an 

in camera review.

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attorneys performing claims-handling functions or investigating insurance claims. “In the 

insurance context, ‘no privilege attaches when an attorney performs investigative work in the 

capacity of an insurance claims adjuster, rather than as a lawyer, [but] simply because [the 

attorney’s] assigned duties were investigative in nature’ does not preclude an assertion of the 

attorney-client privilege.” Arlen House E. Condo. Ass’n, Inc. v. QBE Ins. (Europe) Ltd., No. 07-

23199-CIV, 2008 WL 11333859, at *5 (S.D. Fla. Aug. 27, 2008) (compelling production of 

documents listed on privilege log because counsel did not always act as legal advisor and 

documents do not concern legal advice, but rather were part of the insurer’s standard investigation 

of the claim) (quoting Cutrale Citrus Juices USA, Inc. v. Zurich Am. Ins. Group, No. 5:03-cv-420-

Oc-10GRJ, 2004 WL 5215191, at *3 (M.D. Fla. Sept. 10, 2004)). In other words, “to the extent 

that an attorney acted as a claims adjuster, claims process supervisor, or claim investigations 

monitor, and not as a legal advisor . . . the attorney-client privilege would not apply. . . .” Cutrale 

Citrus Juices, 2004 WL 5215191, at *3. 

Moreover, “communications involving those steps that an insurance company undertakes 

in its ordinary investigation of a claim do not develop privileged status merely because they 

involve an attorney.” 1550 Brickell Ass’n. v. QBE Ins. Corp., 597 F. Supp. 2d 1334, 1337 (S.D. 

Fla. 2009). “In an insurance context, the attorney-client privilege only attaches when an attorney

performs acts for an insurer in his professional capacity and in anticipation of litigation.” 

Milinazzo v. State Farm Ins. Co., 247 F.R.D. 691, 697 (S.D. Fla. 2007).

Similarly, the work-product doctrine only shields discovery of documents or information 

“prepared in anticipation of litigation or for trial.” Fed. R. Civ. P. 26(b)(3). The work product 

doctrine does not apply unless the party asserting work-product demonstrates that it anticipated 

litigation “at the time the materials were created or drafted.” Schulte v. NCL (Bahamas) Ltd., 10-

23265-CIV, 2011 WL 256542, at *2 (S.D. Fla. Jan. 25, 2011) (citing CSX Transp. Inc. v. Admiral 

Ins. Co., 93-132-CIV- J-10, 1995 WL 855421 (M.D. Fla. July 20, 1995)). “[D]ocuments 

constituting any part of a factual inquiry into or evaluation of a claim, undertaken in order to arrive 

at a claim decision, are produced in the ordinary course of an insurer’s business and, therefore, are 

not work product.” Cutrale Citrus Juices, 2004 WL 5215191, at *2.

In the insurance context, moreover, courts in this District utilize a rebuttable presumption 

that “documents or things prepared before the final decision on an insured’s claim are not workproduct, and documents produced after claims denial are work-product.” Milinazzo, 247 F.R.D. at 

Case 1:20-cv-21707-JEM Document 158 Entered on FLSD Docket 08/25/2021 Page 12 of 20
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701; Royal Bahamian Ass’n, Inc. v. QBE Ins. Corp., 268 F.R.D. 695, 698 (S.D. Fla. 2010). “This 

presumption may be rebutted only ‘by specific evidentiary proof of objective facts, that a 

reasonable anticipation of litigation existed when the document was produced.’” Royal Bahamian

Ass’n, Inc., 268 F.R.D. at 698 (quoting Harper v. Auto Owners Ins. Co., 138 F.R.D. 655, 663-64 

(S.D. Ind. 1991) (“To overcome these presumptions, the insurer must demonstrate, by specific 

evidentiary proof of objective facts, that a reasonable anticipation of litigation existed when the 

document was produced, and that the document was prepared and used solely to prepare for that 

litigation, and not to arrive at a (or buttress a tentative) claim decision”). The Insurers cannot 

sustain their burden.

B. The Insurers Have Improperly Withheld from Production Numerous Relevant 

Documents that Pre-Date Any Denial of Coverage

Raymond James requested that each insurer produce the contents of its claim file. While 

the Insurers have produced limited responsive documents, they have withheld as purportedly 

privileged, numerous documents and communications that pre-date their decision to deny coverage

and which clearly relate to the claim investigation. These documents are discoverable because they

“related to [the Insurers’] ‘investigation, processing, analysis’ and ultimate denial of [Raymond 

James’] claim.” Milinazzo, 247 F.R.D. at 696. 

Seacoast 5151 Condo. Ass’n, 2018 WL 6653342, is instructive in this regard. In that case, 

as here, the carrier (Great American) withheld from production, on the basis of the attorney-client 

privilege, numerous communications with its coverage counsel that occurred prior to the decision 

to deny coverage. Id. at *2. The policyholder challenged Great American’s assertion of the 

attorney-client privilege. Id. As Magistrate Judge Bandstra observed, “when the corporation 

asserting attorney-client privilege is an insurance company, the requirements and burden on the 

carrier become even more stringent.” Id. at *3. Generally, the ‘“insurer must demonstrate the 

connection to possible litigation concretely enough to assure the court that it is not simply trying 

to immunize from discovery its routine claims processing material.’” Id. at *3 (quoting Royal

Bahamian Ass’n, Inc., 268 F.R.D. at 698). Consistent with these pronouncements, Magistrate 

Judge Bandstra determined – and the District Court agreed – that Great American must produce 

all documents (with the exception of two preliminary coverage opinions prepared by counsel) 

created prior to its decision to deny coverage for the claim. Id. at *4. As Magistrate Judge Bandstra 

correctly explained:

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Reviewing the documents withheld here or redacted on the basis of the attorneyclient privilege, the undersigned finds that almost all of these documents reflect 

only preliminary communications with counsel well in advance of Great 

American’s decision to deny the HVAC claim so that they are not protected by the 

attorney-client privilege. Coverage counsel William Wilson was first retained on 

or about January 11, 2016—only weeks after the claims were filed by Seacoast and 

almost a full year before Great American denied the HVAC claim on December 27, 

2016. Following his retention, Great American had frequent telephone and email 

contacts with Mr. Wilson to provide him information on the three claims and the 

progress of Great American’s investigation of those claims. Mr. Wilson provided 

input into that investigation and assisted Great American in aspects of that 

investigation relating to information he would need to prepare a coverage opinion 

later that year. No documents listed on Great American's Amended Privilege Log 

contain “specific proof of objective facts” that Great American anticipated 

litigation with Seacoast on any of the three claims prior to the denial of the HVAC 

claim with the possible exception of the written coverage opinion provided by Mr. 

Wilson dated November 22, 2016. Even then, Great American did not deny the 

HVAC claim until December 27—the date certain that Great American could 

reasonably anticipate a lawsuit with Seacoast.

Id. at *4.

Raymond James anticipates that the Insurers may attempt to argue that Magistrate Judge 

Matthewman’s decision in Ranger Constr. Indus., Inc. v. Allied World Nat. Assurance Co., No. 

17-81226-CIV, 2019 WL 436555 (S.D. Fla. Feb. 5, 2019), somehow changes this analysis. It does 

not. At most, Ranger suggests a divergence of opinions in this District only as to whether 

documents must be prepared in anticipation of litigation for the attorney-client privilege to apply. 

Ranger still makes clear, however, that the attorney-client privilege does not apply when counsel 

performs a claim investigation. “Clearly, the privilege should not attach when the attorney is 

working for the corporate insurer solely as a conduit, claims adjustor or a mere claim investigator 

rather than as an attorney rendering legal advice or legal services.” Id. at *6. 

The Insurers, however, are attempting to assert the privilege under those very 

circumstances. Raymond James timely reported a claim of loss in May of 2016, and timely 

provided a proof of loss in February of 2018. Federal did not deny coverage until April 20, 2020. 

The other Defendants similarly denied coverage shortly thereafter. From a review of their privilege 

logs and the portions of the claim files each produced, coupled with the Rule 30(b)(6) deposition 

testimony from each Defendant, it is clear that Defendants conducted their claim investigation 

through counsel, with counsel acting as a claims investigator. Counsel for Defendants, much like 

Case 1:20-cv-21707-JEM Document 158 Entered on FLSD Docket 08/25/2021 Page 14 of 20
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the lawyer in Seacoast, certainly, at the very least, “provided input into the investigation and 

assisted [Defendants] in aspects of that investigation relating to information he would need to 

prepare a coverage opinion later that year.” 2018 WL 6653342, at *4. Tellingly, none of the 

corporate representatives could articulate either what was done to investigate Raymond James’ 

claim for Employee dishonesty or why certain relevant actions either were, or were not,

undertaken.

While many of the entries on the logs are generally described, for example, as 

communications regarding “documentation necessary to provide legal advice,” many of these

withheld documents almost certainly include requests for documentation necessary for counsel to 

investigate the claim and ultimately prepare a coverage letter. And while Federal, for example, has 

indicated that certain documents and communication on its privilege log relate to counsel’s 

analysis of certain case law, given counsel’s role in investigating the claim, it is impossible to tell 

from the description of the documents on the privilege logs whether the entirety of those 

documents contain legal advice or whether the documents contain legal advice mixed with factual 

information learned by counsel as part of the claim investigation. Certainly, the Insurers’ decision 

to have counsel conduct the claim investigation has blurred the line between what arguably 

qualifies as legal advice and what constitutes ordinary claim handling functions. To the extent 

Defendants claim documents contain legal advice, they should therefore, at the very least, be

subject to an in camera review by the Court to determine whether those communications also 

contain discoverable information concerning counsel’s claim investigation on behalf of the 

carriers. Indeed, it was this same counsel that prepared the 28-page letter to Raymond James 

denying coverage.

Based on the law in this District, Raymond James is entitled to those documents evidencing 

what was being done by the Insurers to arrive at their claim decision, regardless of whether the 

investigation was being done by counsel. This would include, for example, any facts 

communicated between the Insurers and counsel and any communications describing what counsel 

was being asked to investigate, or was investigating, as part of the claim process. 

“[C]ommunications involving those steps that an insurance company undertakes in its ordinary 

investigation of a claim do not develop privileged status merely because they involve an attorney.” 

1550 Brickell Ass’n, 597 F. Supp. 2d at 1337. 

Moreover, many of the entries on the privilege logs relate to documents created long before 

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Federal denied coverage on April 20, 2020. Plainly, all of these documents could not possibly have 

been prepared in anticipation of litigation as opposed to the Insurers’ non-delegable duty to 

investigate, evaluate and adjust the claim. Any documents created prior to the denial of coverage 

are presumed discoverable, and the Insurers cannot meet their burden of demonstrating otherwise. 

There is nothing in the privilege log descriptions to suggest a reasonable anticipation of litigation 

existed when the documents were created – particularly as to those documents generated or 

received prior to even denying coverage for the claim.

Lastly, the common interest privilege asserted by the carriers is not a sufficient basis to 

withhold otherwise discoverable documents. The joint defense or common interests doctrine “is 

an extension of the work product doctrine and allows parties facing a common litigation opponent 

to exchange privileged communications and attorney work product in order to prepare a common 

defense without waiving either privilege.” Fojtasek v. NCL (Bahamas) Ltd., 262 F.R.D. 650, 654 

(S.D. Fla. 2009). In other words, it is a necessary condition of the common interest doctrine that 

the documents otherwise be privileged in the first instance. Because the documents at issue are not 

protected from disclosure under the attorney-client privilege and/or the work-product doctrine, the 

common interest privilege is unavailing.

In short, the Insurers have improperly withheld from production, as purportedly privileged, 

numerous documents and communications that pre-date Federal’s April 20, 2020 decision to deny

coverage and which clearly relate to their claim investigation. Their privilege assertions should be 

overruled and they should be ordered to produce to Raymond James all such documents and 

communications that were created or received prior to April 20, 2020, as well as the “market” 

communications prior to April 20, 2020. Having retained counsel to handle the claim investigation 

each Defendant was required to conduct, Defendants should not now be heard to argue that those 

documents and communications are protected by the attorney-client privilege and/or work product 

doctrine. Florida law clearly says they are not.

At the very least, the Insurers should be ordered to submit the documents to the Court for 

an in camera review, because there is nothing included in Defendants’ general descriptions of the 

documents in the privilege logs that would allow this Court to determine that these documents are

otherwise protected, in whole or in part. See, e.g., AIG Centennial Ins. Co. v. O'Neill, No. 09-

60551-CIV-ZLOCH, 2010 WL 4116555, at *9 (S.D. Fla. Oct. 18, 2010) (directing insurer to file 

in camera the documents for which it claimed privilege). However, “it is wise for the Court to 

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not consider an in camera review until the party asserting privilege has done all that it reasonably 

could to establish privilege. In camera review ‘is not to be used as a substitute for a party's 

obligation to justify its withholding of documents.’” Campero USA Corp. v. ADS Foodservice, 

LLC, 916 F. Supp. 2d 1284, 1289, n.4 (S.D. Fla. 2012).

CONCLUSION

Based on the foregoing, Raymond James respectfully requests that this Court enter an 

Order overruling the Insurers’ privilege objections as to documents that pre-date April 20, 2020

and compelling their production, compelling the Insurers to produce the “market” communications 

dated between December 19, 2019 and April 20, 2020, and directing the Insurers to each produce 

a corporate representative to testify as to the substance of those communications prior to the trial 

in this matter.

Date: August 25, 2021 Respectfully submitted,

/s/ Jason S. Mazer

Jason S. Mazer, Esq. 

Florida Bar No. 0149871 

Joshua R. Alhalel, Esq. 

Florida Bar No. 0016320

CIMO MAZER MARK PLLC

100 Southeast Second Street, Suite 3650

Miami, Florida 33131

Telephone: (305) 374-6481

Fax: (305) 374-6488

jmazer@cmmlawgroup.com

jalhalel@cmmlawgroup.com

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LOCAL RULE 7.1 CERTIFICATION

Pursuant to Local Rule 7.1(a)(3)(A), I hereby certify that the undersigned has conferred 

numerous times with counsel for Defendants by electronic mail on August 24, 2021, and was 

unable to resolve this discovery dispute. 

CERTIFICATE OF SERVICE

I hereby certify that on August 25, 2021, I electronically filed this Motion to Compel and 

Memorandum of Law with the Clerk of Court using CM/ECF. I also certify that the foregoing 

document is being served this day on parties listed in the below Service List via transmission of 

Notices of Electronic Filing generated by CM/ECF. 

/s/ Jason S. Mazer

Case 1:20-cv-21707-JEM Document 158 Entered on FLSD Docket 08/25/2021 Page 18 of 20
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SERVICE LIST

Kristina L. Marsh, Esq. 

Florida Bar No. 0311080

GORDON REES SCULLY 

MANSUKHANI

601 S. Harbor Island Blvd., Suite 109

Tampa, FL 33602

Telephone (Main): 813-444-9700

Telephone (Direct) 813-523-4937

Facsimile: 813-377-3505

kmarsh@grsm.com

afiorito@grsm.com

cflores@grsm.com

fgude@grsm.com

kwatson@grsm.com

Tampapleadings@grsm.com

and

Scott L. Schmookler, Esq.

Sarah Riedl Clark, Esq.

Chantal Christine Wonder, Esq.

Angel Lewosz, Esq.

GORDON REES SCULLY 

MANSUKHANI

One North Franklin, Suite 800

Chicago, IL 60606

Telephone: 312-980-6779

sschmookler@grsm.com

srclark@grsm.com

cwonder@grsm.com

aruff@grsm.com

alewosz@grsm.com

Counsel for Federal Insurance Company

James M. Kaplan, Esq. 

Florida Bar No. 921040

KAPLAN ZEENA LLP

2 South Biscayne Boulevard, Suite 3050

Miami, Florida 33131

Telephone: (305) 530-0800

Facsimile: (305) 530-0801

James.kaplan@kaplanzeena.com

Elizabeth.salom@kaplanzeena.com

service@kaplanzeena.com

and

Michael Keeley, Esq.

John R. Riddle, Esq.

Clark Hill Strasburger

901 Main Street, Suite 6000

Dallas, Texas 75202-3794

Telelphone: (214) 651-4718

Facsimile: (214) 659-4121

mkeeley@clarkhill.com

jriddle@clarkhill.com

Counsel for Beazley Insurance Company, Inc.

Case 1:20-cv-21707-JEM Document 158 Entered on FLSD Docket 08/25/2021 Page 19 of 20
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E.A. “Seth” Mills, Jr., Esq. 

Florida Bar No. 339652 

Ryan J. Weeks, Esq.

Florida Bar No. 57897

MILLS PASKERT DIVERS

100 N. Tampa Street, Suite 3700

Telephone: (813) 229-3500

Facsimile: (813) 229-3502

smills@mpdlegal.com

rweeks@mpdlegal.com

csoltis@mpdlegal.com

Counsel for Travelers Casualty and Surety 

Company of America

Dustin C. Blumenthal

Florida Bar No. 0149871 

Goldberg Segalla

222 Lakeview Avenue, Suite 800

West Palm Beach, FL 33401

Telephone: (561) 618-4485

Facsimile: (561) 618-4549

dblumenthal@goldbergsegalla.com

lparker@goldbergsegalla.com

and

Stephen N. Dratch, Esq.

Julian Wilsey, Esq.

Franzblau Dratch, P.C.

354 Eisenhower Parkway

Livingston, New Jersey 07039

Telephone: (973) 992-3700

sdratch@njcounsel.com

jwilsey@njcounsel.com

Counsel for Great American Insurance 

Company

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