NOT FINAL UNTIL TIME EXPIRES TO FILE REHEARING

MOTION AND, IF FILED, DETERMINED

IN THE DISTRICT COURT OF APPEAL

OF FLORIDA

SECOND DISTRICT

DANIEL T. HESTER, an individual, )

)

Appellant, )

)

v. ) Case No. 2D15-1167

)

FLORIDA CAPITAL GROUP, INC., a )

Florida corporation; CHARLES E. )

HUGHES, an individual; and J. MALCOLM )

JONES, JR., an individual, )

)

Appellees. )

)

Opinion filed March 30, 2016.

Appeal from the Circuit Court for Pinellas 

County; Walter L. Schafer, Jr., Judge.

John E. Johnson and Christopher L. 

DeCort of Johnson & Cassidy, P.A., 

Tampa, for Appellant.

Christopher L. Griffin of Foley & Lardner

LLP, Tampa; and John S. Lord, Jr. and 

Christina M. Kennedy of Foley & Lardner

LLP, Orlando, for Appellees.

MORRIS, Judge.

Daniel T. Hester appeals an order dismissing with prejudice his complaint 

against Florida Capital Group, Inc.; Charles E. Hughes; and J. Malcom Jones, Jr.
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(collectively referred to as the appellees), for breach of Hester's employment 

agreement, fraud, negligent misrepresentation, and declaratory and injunctive relief. In 

a pretrial effort to resolve the disputes, the parties entered into a settlement agreement, 

but the parties later disputed the enforceability of certain terms of that agreement. The 

trial court granted the appellees' motion to enforce the settlement agreement and 

entered an order dismissing Hester's complaint. On appeal, Hester challenges the trial 

court's interpretation of the terms of the settlement agreement. We reverse for the 

reasons explained below. 

I. Facts and procedural background

Florida Capital Group, Inc. (the Bank), operates a national banking 

association with an office in Pinellas County. Hughes and Jones were officers of the 

Bank, and Hester was employed by the Bank as an executive. After Hester's 

employment was terminated, he initiated the underlying litigation in 2010. In 2011, the 

parties participated in mediation and reached an initial settlement that was contingent 

upon regulatory approval from governmental agencies. The approval was not obtained, 

and the parties recommenced settlement discussions in 2012. On July 18, 2012, the 

parties executed the settlement agreement at issue in this appeal. 

The agreement provides that Hester will dismiss his complaint against the 

appellees in exchange for the payment of certain sums by the appellees. The 

agreement also provides that the sums are subject to approval by the necessary 

regulatory agencies. More specifically, the agreement provides as follows:

2. The parties shall submit to the necessary federal 

regulatory entities, including as necessary the Federal 

Reserve, the Federal Deposit Insurance Corporation 

[(FDIC)], and/or the Office of Comptroller of the Currency, 
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within 10 days of the execution of this Agreement (the 

"Submission Date"), for approval of the payment of the sums 

set forth in Section 3 within six months from the Submission 

Date. The parties agree to stay all active litigation, including 

but not limited to all discovery, until after the expiration of 

this six[-]month period.

3. In consideration for Hester's promises and 

covenants contained in this Agreement, Florida Capital, 

Hughes and Jones agree to pay Hester the total settlement 

amount of $500,000.00 (the "Settlement Amount"), broken 

down as follows: Florida Capital will pay to Hester the gross 

amount of $160,000.00 for claimed severance pay; Florida 

Capital will pay to Hester the gross amount of $40,000.00 for 

claimed attorneys' fees and costs; and Florida Capital's, 

Hughes' and Jones' insurance carrier, The Travelers 

Companies, Inc., will pay to Hester the gross amount of 

$300,000.00 for claimed compensatory damages for the 

negligence claims; provided however the parties agree that 

any and all payments agreed to in this Agreement are 

subject to advance approval by the necessary regulatory 

entities. Said amounts will be delivered within 15 days after 

Hester, Florida Capital, Hughes and Jones receive the 

necessary regulatory approvals for any respective payment. 

. . . After regulatory approval is received for the Settlement 

Amount, the payments will be made as follows: a check in 

the amount of $160,000.00, payable to Hester, representing 

payment for claimed severance pay . . . ; a check in the 

amount of $300,000.00, payable to Hester, representing 

payment for claimed compensatory damages for the 

negligence claims . . . ; and a check in the amount of 

$40,000.00, payable to Hester's lawyer's firm, representing 

payment for attorney's fees and costs alleged in the Lawsuit 

. . . . In the event that regulatory approval is received for a 

total amount equal to or greater than $350,000.00, but not 

for the Settlement Amount--or for an amount less than 

$350,000.00 and Hester provides Florida Capital, Hughes 

and Jones with the written confirmation of acceptance of 

said amount as detailed in Section 6--the payments will be 

made proportionally in accordance with the breakdown 

provided in this Section.

4. If regulatory approval is received for the 

Settlement Amount, Hester will dismiss with prejudice the 

Lawsuit no later than five days after receipt of payment of 

those sums, by filing a notice of dismissal with prejudice with 

the court.
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5. If regulatory approval is received for a total amount 

of $350,000.00 or greater, Hester will dismiss with prejudice 

the Lawsuit no later than five days after receipt of payment 

of those sums, by filing a notice of dismissal with prejudice 

with the court. 

6. If regulatory approval is received for a total amount 

less than $350,000.00, Hester will have the sole option to 

accept or reject payment of the approved amount that is less 

than $350,000.00, by sending written confirmation of said 

acceptance or rejection to Florida Capital, Hughes and 

Jones within 15 days of receiving regulatory approval. If 

Hester accepts the approved amount that is less than 

$350,000.00, Hester will dismiss with prejudice the Lawsuit 

no later than five days after receipt of payment of those 

sums, by filing a notice of dismissal with prejudice with the 

court. If Hester does not accept the approved amount that is 

less than $350,000.00, the active litigation shall continue 

under the pre-determined schedule set forth in Section 7.

7. In the event that the necessary federal regulatory 

entities fail to respond to the submission for approval as set 

forth in Section 2 within six months of the Submission Date, 

upon expiration of the six[-]month period referenced in 

Section 2 the active litigation shall continue under the 

following pre-determined schedule, which shall be agreed to 

by the parties and submitted to the court with jurisdiction 

over the Lawsuit as a condition of this Agreement . . . .

(Emphasis added.) Section 7 of the agreement further provides that depositions and 

discovery would be concluded in March 2013, that all dispositive motions would be 

heard in April 2013, and that a jury trial in Pinellas County would commence no later 

than June 1, 2013. Section 8 of the agreement provides that Hester will accept "regular 

early termination benefits available to him pursuant to the [Supplemental Executive 

Retirement Plan (SERP)]" and that he will not seek any enhanced early termination 

benefits under the SERP. Further, the Bank is required to begin paying Hester the 

SERP payments within forty-five days, including a lump sum payment for the SERP 

payments that had accrued since his termination. 
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Pursuant to Section 2 of the agreement, in July 2012, Hester and the 

appellees submitted to the regulatory agencies an application for approval of the 

agreed-upon payments in Section 3, but the regulators failed to respond to the 

application within six months. On February 8, 2013, Hester filed an unopposed motion 

to set the matter for trial, and on November 1, 2013, the parties filed a joint stipulation to 

set the cause for trial in February 2014. 

Approximately a year and a half after the parties submitted the application 

to the regulatory agencies, the Bank sent Hester a letter advising him that the Bank had 

"received confirmation from the FDIC that Mr. Hester may be paid $300,000 as part of 

the settlement." The FDIC letter, dated December 18, 2013, stated that the $300,000 

payment by the Bank's insurer did not require regulatory approval. The FDIC letter 

further stated, however, that the $160,000 and $40,000 proposed payments constituted 

"golden parachute payments" that required regulatory approval. The FDIC determined 

that "[a]ny amount in excess of twelve months' salary, including the $40,000 for 

attorney's fees, would constitute an impermissible golden parachute payment." As to 

that portion of the settlement, the FDIC indicated that it was prepared to deny the 

application but that it would consider a revised application if submitted within thirty days. 

The Bank stated in its letter to Hester that it was submitting a revised application to the 

FDIC requesting that it be allowed to pay him a golden parachute payment of $160,000.

On December 23, 2013, Hester sent the Bank a letter rejecting the offer of 

$300,000. Hester noted that the settlement agreement had "expired by its own terms 

and is of no further force or effect." Hester objected to any "stay relief that is premised 

upon the [B]ank's unilateral submission to the FDIC" of a new application. Hester 
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counteroffered to settle his claims for a total of $760,000. In April 2014, Hester made 

another offer to settle his claims for a total of $720,000. In May 2014 and again in 

August 2014, the appellees offered to have their insurance company pay Hester 

$350,000 and then submit a new application to their regulators for an additional 

payment of $160,000, for a total settlement of $510,000. Upon receiving no response 

from Hester, the appellees filed a motion to enforce the settlement agreement, arguing 

that the appellees had offered to pay $350,000 and an additional $160,000 if regulatory 

approval was obtained.

Following two hearings on the appellees' motion to enforce, the trial court 

entered an order approving and enforcing the settlement agreement in September 

2014. The trial court found that the agreement is clear and unambiguous and that the 

six-month period in the agreement referred to a period of non-litigation rather than an 

expiration date for the agreement. The court further found that the appellees' total offer 

to Hester of $510,000 met the terms of the settlement agreement. The trial court 

directed the Bank to pay $350,000 to Hester and to submit the necessary paperwork for 

regulatory approval to pay him an additional $160,000, with payment to be made within 

ten days of receipt of such approval. The court also found that under the agreement, 

the appellees are prevailing parties for purposes of attorneys' fees and costs. Hester 

attempted to appeal the September 2014 order, but this court dismissed the appeal as 

being from a nonfinal, nonappealable order. Hester entered into a stipulation with the 

appellees whereby the trial court entered a final order dismissing the case with 

prejudice, so that Hester could appeal the trial court's ruling enforcing the payment 

terms of the settlement agreement.
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II. Analysis

On appeal, Hester argues that the trial court erred in enforcing certain 

payment provisions of the agreement that he claims had expired. He contends that the 

terms of the agreement clearly and unambiguously provide that the payment provisions 

in Sections 3 through 6 were contingent upon regulatory approval being received within 

six months. Hester claims that because regulatory approval was not received within six 

months, he was not required to accept those payments. He argues that other 

provisions of the agreement did not expire after any specific period of time, e.g., the 

provisions regarding the SERP payments in Section 8, and that those provisions 

became binding at execution of the agreement and are enforceable. The appellees, on 

the other hand, argue that the trial court correctly ruled that the agreement does not 

contain an expiration date for regulatory approval; the agreement only stayed the active 

litigation during a six-month period. The appellees contend that the agreement did not 

require the regulatory approval to be obtained within six months in order for the 

payment provisions to be valid.1

The interpretation of settlement agreements is governed by contract law. 

Gira v. Wolfe, 115 So. 3d 414, 417 (Fla. 2d DCA 2013). We review de novo the trial 

court's interpretation of the agreement in this case as a matter of law, and in doing so, 

we "may reach a construction or interpretation of the contract contrary to that of the trial 

court." Bethany Trace Owners' Ass'n v. Whispering Lakes I, LLC, 155 So. 3d 1188, 

1191 (Fla. 2d DCA 2014). "The cardinal rule of contractual construction is that when the 

language of a contract is clear and unambiguous, the contract must be interpreted and 

 

1We note that neither Hester nor the appellees argue that the terms of the 

agreement are ambiguous. 
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enforced in accordance with its plain meaning." CitiMortgage, Inc. v. Turner, 172 So. 3d 

502, 504 (Fla. 1st DCA 2015) (quoting Columbia Bank v. Columbia Developers, LLC, 

127 So. 3d 670, 673 (Fla. 1st DCA 2013)). "When interpreting contractual provisions, 

courts 'will not interpret a contract in such a way as to render provisions meaningless 

when there is a reasonable interpretation that does not do so.' " Bethany Trace Owners' 

Ass'n, 155 So. 3d at 1191 (quoting Moore v. State Farm Mut. Auto. Ins. Co., 916 So. 2d 

871, 877 (Fla. 2d DCA 2005)).

We agree with Hester that the language of the agreement is clear and 

unambiguous in that it requires regulatory approval of the payment terms in Sections 3 

through 6 within six months.2 Specifically, Section 2 states that "[t]he parties shall 

submit to the necessary federal regulatory entities . . . for approval of the payment of 

sums set forth in Section 3 within six months from the Submission Date." (Emphasis 

added.) This language clearly expresses an intent that the regulatory approval be 

received within six months. Section 2 goes on to provide that all active litigation would 

be stayed "until after the expiration of this six[-]month period." Had the underlined 

language above not been included in the agreement, the trial court's interpretation (and 

the appellees' interpretation) of the agreement would be reasonable. If the underlined 

language requiring approval within six months had been omitted, the six-month time 

period would have simply been a stay of litigation and nothing more. But Section 2 

clearly requires regulatory approval of the agreed-upon payments within six months. To 

 

2The breakdown of the agreed-upon settlement amount is set forth in 

Section 3, and Sections 4 through 6 in turn address if regulatory approval is received in 

the settlement amount, in an amount of $350,000 or greater, or in an amount less than 

$350,000. 
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read Section 2 otherwise—as simply being a stay of litigation—would render 

meaningless the language referring to approval within six months. 

The language of Section 7 of the agreement further demonstrates that the 

parties intended for the regulatory approval to be received within six months in order for 

the payment terms of Sections 3 through 6 to take effect. Section 7 provides for a 

litigation schedule "[i]n the event that the necessary federal regulatory entities fail to 

respond to the submission for approval as set forth in [s]ection 2 within six months of 

the Submission Date" and "upon expiration of the six[-]month period referenced in 

Section 2." (Emphasis added.) This language reflects the parties' intent that regulatory 

approval be received within six months in order to trigger the payment provisions in 

Sections 3 through 6. This language also reflects the parties' intent that if such timely 

approval was not received, the litigation would continue on Hester's claims mentioned in 

Section 3 in accordance with the schedule provided in Section 7. If the parties had 

contemplated that regulatory approval could be received after the six-month period had 

expired and that litigation would again be stalled in the future, the litigation schedule 

outlined in section 7 would be meaningless. We note that there is no language in the 

agreement regarding what would happen to the litigation if regulatory approval were to 

be received after six months, further supporting the conclusion that the parties did not 

intend for approval to be received after six months for purposes of the payment 

provisions in Sections 3 through 6.

The appellees argue that the agreement does not contain an expiration 

date, but Hester does not argue that the entire agreement contains an expiration date. 

Rather, he argues, and we agree, that the payment provisions in Sections 3 through 6 
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took effect only if the regulatory approval was received within six months of the date the 

application was submitted. 

Because the only reasonable interpretation of the agreement requires 

regulatory approval of the payment terms in Sections 3 through 6 within six months and 

because regulatory approval was not received within six months, the trial court erred in 

concluding that the payment terms in Sections 3 through 6 are enforceable against 

Hester.3 In light of our determination on this issue, we need not address Hester's 

remaining arguments on appeal. We reverse the final order dismissing Hester's 

complaint with prejudice and remand for further proceedings consistent with this 

opinion.

Reversed and remanded.

KELLY and CRENSHAW, JJ., Concur.

 

3Even though the trial court concluded that the agreement is 

unambiguous, it noted an expiration provision that had been included in an earlier draft 

of the agreement but was stricken from the final agreement. Only if the terms are 

latently ambiguous should a trial court consider extrinsic evidence in determining the 

intent of the parties. See Emergency Assocs. of Tampa, P.A. v. Sassano, 664 So. 2d 

1000, 1002-03 (Fla. 2d DCA 1995) (discussing the difference between a patent and 

latent ambiguity and holding that a trial court is authorized to consider parol evidence 

when a latent ambiguity exists, i.e., when a contract is clear and unambiguous on its 

face but fails to specify the rights and duties of the parties in certain situations). 

Because the agreement in this case is clear and unambiguous regarding the factual 

situation presented in this case, resort to extrinsic evidence is not necessary.