13‐1050‐cv

StreetEasy, Inc. v. Chertok

UNITED STATES COURT OF APPEALS

FOR THE SECOND CIRCUIT

                               

August Term, 2013

(Submitted: February 10, 2014    Decided: June 5, 2014)

Docket No. 13‐1050‐cv

                                  

STREETEASY, INC.,

Plaintiff‐Appellee,

— v. —

DOUGLAS CHERTOK,

Defendant‐Appellant.

*

__________________

B e f o r e:

JACOBS, LIVINGSTON, and LYNCH, Circuit Judges.

__________________

*

After the notice of appeal was filed in this case, Plaintiff‐Appellee NMD

Interactive, Inc. changed its name to StreetEasy, Inc.  The Clerk of Court is

directed to amend the official caption to conform with the caption above.  

1
Douglas Chertok, pro se, New York, New York, for Defendant‐

Appellant.

Emily S. Reisbaum, Isaac  Zaur, Clarick Gueron Reisbaum LLP, New

York, New York, for Plaintiff‐Appellee.

__________________

Plaintiff‐appellee StreetEasy,Inc. sueddefendant‐appellantDouglas Chertok

under (inter alia) the Anticybersquatting Consumer Protection Act, 15 U.S.C.

§ 1125(d).  The parties entered into a settlement agreement on the record before the

magistrate judge, and stipulated to a dismissal of the suit with prejudice.  When

Chertok subsequently moved to vacate the order of dismissal and to rescind the

settlement agreement, the United States District Court for the Southern District of

New York (Richard J. Sullivan, Judge) granted plaintiff’s cross‐motion to enforce the

settlement agreement, imposed sanctions on Chertok for propounding unfounded

factual contentions, and ultimately held the defendant in contempt for

noncompliance with the court’s enforcement order.  Because thedistrict courtlacked

jurisdiction to enforce the parties’ settlement agreement, we vacate the orders

enforcing the settlement agreement and holding Chertok in contempt; we vacate the

2
district court’s award of sanctions, and remand the case for reconsideration of the

proper amount of the sanctions in light of this opinion.         

__________________

GERARD E. LYNCH, Circuit Judge:

This appeal arises out of the attempted resolution of a dispute between a

real estate listing website and one of its co‐founders over the propriety of actions

taken by the co‐founder when he separated from the company in 2007, and the

validity of corporate actions that occurred before his departure.  It requires us to

decide whether the district court had jurisdiction to enforce a settlement

agreement that resulted in the dismissal of the underlying case.  We must also

decide whether the district court properly exercised its authority under Federal

Rule of Civil Procedure 11 to sanction the defendant for proffering unfounded

factual contentions in his filings with and oral representations to the court.

Because the order of dismissal failed to retain jurisdiction over enforcement of

the parties’ settlement agreement, or to incorporate the terms of that agreement,

the district court lacked jurisdiction to enforce the agreement.  Accordingly, we

vacate the district court’s orders enforcing the settlement agreement and holding

the defendant in contempt for noncompliance.  In addition, because the

3
defendant was properly sanctioned for only one of the three factual contentions

identified by the district court as the basis for its sanctions award, we vacate that

award and remand the matter for reconsideration of the appropriate amount of

monetary sanctions in light of this decision.    

BACKGROUND

Appellee StreetEasy, Inc. (“StreetEasy”) operates a website that provides

real estate listings and related information to brokers and the public.1

  Appellant

Douglas Chertok (“Chertok”) co‐founded StreetEasy in or around 2005 with

nonparties Michael Smith (“Smith”), Anthony Schmitz, and Nataly Kogan.2

  In

the process of establishing StreetEasy, Chertok registered the domain name

“streeteasy.com.”  In August 2006, StreetEasy sought and obtained $2.5 million in

venture capital financing by issuing preferred stock (the “Series A Stock Sale”).

Consummation of this transaction required certain actions to be taken by the

1

  Appellee formerly operated under the name NMD Interactive, Inc. but has

since changed its name to StreetEasy, Inc.

2

  Chertok contends that he alone founded StreetEasy.  This contention directly

contradicts his representation in the parties’ settlement agreement.  Nonetheless,

because it is irrelevant to this appeal whether Chertok founded or co‐founded

StreetEasy, we will not address the matter further.

4
company’s board and shareholders.3

  The parties strongly dispute whether these

corporate actions were validly effected.  While StreetEasy claims that approval

was obtained through telephonic board and shareholder meetings in which

Chertok participated on August 29, 2006, Chertok contends that approval was

fabricated as part of a scheme by Smith — StreetEasy’s Chief Executive Officer —

to usurp control of the company.  

Around the same time that StreetEasy was negotiating the venture capital

investment, Chertok’s relationship with the company began to sour.  StreetEasy

alleges that in the summer of 2006 the company discovered that Chertok had

embezzled $55,000.  Upon making this discovery, the company severed all

relations with Chertok, removing him as a co‐signer on the company’s bank

account and later electing a new board of directors that excluded Chertok.  After

Chertok and StreetEasy parted ways, Chertok allegedly refused to provide the

company with possession and control of its domain names, including

3 These actions included approval of a reserve stock split and related adjustments

to the company’s certificate of incorporation, a change to the number of shares

held by each of the company’s founders, authorization and issuance of Series A

preferred stock, an increase in the size of the board of directors, and approval of

documents memorializing the financing.

5
“streeteasy.com.”4

  StreetEasy also claims that in 2011 Chertok attempted to gain

access to the company’s bank records by falsely representing to bank staff that he

was still associated with StreetEasy.  

Following these actions by Chertok, StreetEasy initiated suit in the

Southern District of New York, asserting claims under the Anticybersquatting

Consumer Protection Act, 15 U.S.C. § 1125(d), as well as claims for breach of a

fiduciary duty and conversion, and requesting a declaratory judgment that

Chertok has no continuing relationship with StreetEasy.  After commencement of

the action, Chertok took the position that the 2006‐2007 corporate actions –

including the election of a new board of directors – were invalid, because he was

allegedly the sole board member at the time of those actions, and he allegedly

had not approved them.  Chertok agreed, however, to transfer control of the

domain names to StreetEasy.  StreetEasy then amended its complaint,

maintaining its previously asserted claims, and adding claims for a declaratory

judgment that the corporate actions taken in August 2006 and StreetEasy’s

election of a new board of directors in 2007 were valid.

4 In 2011, Chertok also allegedly registered two additional domain names –

streeteasy.org and streeteasy.info.

6
On January 24, 2012, after limited discovery, the parties reached a

settlement agreement during a settlement conference with Magistrate Judge

Andrew J. Peck.  Judge Peck stated the terms of the parties’ agreement, and the

parties confirmed their consent to the agreement, on the record.  Pursuant to the

settlement, Chertok agreed, among other things, to (1) transfer to StreetEasy any

and all StreetEasy Internet domain names that he had not already transferred,

and not to register any similar domain names; (2) acknowledge that his

involvement with StreetEasy, other than as a shareholder, ended in October 2007,

and that he would not hold himself out as a representative of StreetEasy; (3)

“ratif[y] and consent[] to the actions taken at the August 29, 2006 board and

shareholder meetings and . . . sign any and all documents required by that,

including the action by written consent dated as of August 30, 2006”; (4)

acknowledge that the revised certificate of incorporation and bylaws are valid;

and (5) sign the Series A Stock Sale documents.  In return, StreetEasy agreed,

among other things, to create an “About Us” page on its website recognizing

Chertok’s contribution to the company, and to provide Chertok with certain

financial documents each calendar quarter.  Both parties also agreed “to execute

mutual general releases so that the company releases Mr. Chertok and his

7
company, and Mr. Chertok releases StreetEasy and its management, employees,

directors, and shareholders, in the immortal words of the Blumberg form, from

any and all causes of action from the beginning of the world to the date of this

settlement agreement and release,” and that the case would be dismissed with

prejudice.

At the conclusion of the conference, Judge Peck informed the parties that

they now had “a binding settlement agreement,” and that “[n]o settlement

agreement documents [were] necessary.”  While “the releases and series A

transaction documents, . . . [and other] paperwork need[ed] to be completed,”

there was “not going to be drafted a more formal settlement agreement,” because

“[t]he transcript constitute[d] the agreement.” By order dated January 25, 2012,

Judge Peck dismissed the action with prejudice.  That order states:

Based on the settlement agreement reached by all

parties and transcribed by the court reporter on January

24, 2012, and on the stipulation of the parties pursuant

to 28 U.S.C. § 636(c), IT IS HEREBY ORDERED THAT

this action is dismissed with prejudice and without

costs.  Any pending motions are to be terminated as

moot.

Unfortunately, the repose anticipated by the parties’ settlement agreement

did not last long.  Within days of entering the settlement agreement, StreetEasy

8
sought Chertok’s signature on a number of documents associated with the Series

A Stock Sale, including an August 30, 2006 Action by Written Consent in Lieu of

a Meeting of Stockholders and an August 30, 2006 Written Consent in Lieu of

Special Meeting of Board of Directors.  Chertok’s counsel then sought and

received from StreetEasy the closing binder for the 2006 Series A Stock Sale that

had been prepared by StreetEasy’s former legal counsel Proskauer Rose LLP

(“Proskauer”).  The closing binder contained a number of documents that, in

Chertok’s view, substantiated his earlier contention that the 2006‐2007 corporate

actions were unauthorized.  In particular, the binder included Proskauer’s

written opinion that the 2006 Series A Stock Sale was properly approved by the

stockholders by a written consent dated August 30, 2006 (“Proskauer Opinion”).5

It also contained partially executed copies of Backup and Compliance Certificates

related to the Series A Stock Sale.

On May 9, 2012, after relieving counsel who had represented him during

the settlement, Chertok moved, pro se, to vacate the order of dismissal and

rescind the settlement agreement pursuant to Federal Rule of Civil Procedure

5 Because Chertok had not signed the written stockholder consent, he contends

that the Proskauer Opinion “fraudulent[ly]” stated that the transaction was

properly approved.  

9
60(b).  Chertok argued that the settlement should be rescinded because

StreetEasy had fraudulently concealed the Proskauer Opinion and the Backup

and Compliance Certificates from him prior to the settlement, and that these

documents constituted newly discovered evidence of which Chertok was

justifiably ignorant that would have altered the outcome of the case.  StreetEasy

responded with a motion to compel compliance with the parties’ settlement

agreement, and soon thereafter moved for sanctions against Chertok, seeking the

fees and costs associated with litigating Chertok’s Rule 60(b) motion and the

motion for sanctions itself.  StreetEasy argued that sanctions were justified

because Chertok’s motion contained deliberate falsehoods and lacked a

reasonable basis in law.  On March 18, 2013, the district court denied Chertok’s

Rule 60(b) motion, granted StreetEasy’s motion to enforce the settlement

agreement, and granted StreetEasy’s motion for sanctions.  

Thereafter, the parties continued to disagree about the scope of Chertok’s

obligations under the settlement agreement.  On April 2, Chertok was ordered to

show cause why he should not be held in contempt for refusing to comply with

the Court’s March 18 Order directing his compliance with the settlement

agreement, and on April 25 he was held in contempt, fined $5,000 a day for his

10
noncompliance, and ordered to pay fees and costs incurred by the plaintiff as a

result of Chertok’s noncompliance.  That evening, Chertok signed and delivered

a mutual release contemplated by the settlement agreement.  The following day,

the district court issued an order relieving Chertok from the contempt order and

instructing him to pay $5,000 for his one day in contempt.  Finally, on September

25, the district court ordered Chertok to pay $69,773.75 in attorneys’ fees and

costs to the plaintiff, representing the Rule 11 sanctions imposed by the court and

the attorneys’ fees incurred by and awarded to the plaintiff after the Order to

Show Cause hearing.  Chertok now appeals the district court’s orders enforcing

the parties’ settlement agreement, imposing sanctions, holding him in contempt,

and setting the amount of attorneys’ fees and costs to be paid to plaintiff‐

appellee.6

              

6 On appeal, Chertok does not challenge the district court’s decision to deny his

Rule 60(b) motion.  In his opening brief, Chertok raised for the first time an

argument that the order of dismissal should be vacated and the settlement

rescinded because the plaintiff‐appellee allegedly defrauded the district court,

but he has since withdrawn that argument.   

11
DISCUSSION

I. Enforcement of Settlement and Contempt7    

“A federal court does not automatically retain jurisdiction to hear a motion

to enforce or otherwise apply a settlement in a case that it has previously

dismissed.”  In re Am. Express Fin. Advisors Sec. Litig., 672 F.3d 113, 134 (2d Cir.

2011) (citing Kokkonen v. Guardian Life Ins. Co. of Am., 511 U.S. 375, 380‐82

(1994)).  “Such motions are essentially state‐law contract claims.”  Id.  Where,

however, the federal court makes “the parties’ obligation to comply with the

terms of the settlement agreement . . . part of the order of dismissal — either by

separate provision (such as a provision ‘retaining jurisdiction’ over the settlement

agreement) or by incorporating the terms of the settlement agreement in the

order” — that court is a proper forum for litigating a breach of the settlement

agreement.  Id. (quoting Kokkonen, 511 U.S. at 381) (ellipsis in original); accord

Perez v. Westchester County Dep’t of Corr., 587 F.3d 143, 151‐53 (2d Cir. 2009).

In such cases the district court “necessarily ma[kes] compliance with the terms of

the [settlement] agreement a part of its order so that ‘a breach of the agreement

7 In reviewing a district court’s decision whether to enforce a settlement

agreement, we review its findings of fact with respect to the agreement for clear

error and its legal conclusions de novo.  See Omega Eng’g, Inc. v. Omega, S.A.,

432 F.3d 437, 443 (2d Cir. 2005).

12
would be a violation of the order,’”  Roberson v. Giuliani, 346 F.3d 75, 82 (2d Cir.

2003) (quoting Kokkonen, 511 U.S. at 381), and the district court may therefore

enforce the settlement as an exercise of its ancillary jurisdiction to “manage its

proceedings, vindicate its authority, and effectuate its decrees,” Kokkonen, 511

U.S. at 380.    

Here, the district court concluded that it had jurisdiction to enforce the

terms of the parties’ settlement agreement because the dismissal order

“[p]lainly . . . incorporated the Settlement.”  We disagree.  The order dismissing

the underlying case provided that “[b]ased on the settlement agreement reached

by all parties and transcribed by the court reporter on January 24, 2012, . . . IT IS

HEREBY ORDERED THAT this action is dismissed with prejudice and without

costs.”  The order does not expressly retain jurisdiction over enforcement of the

agreement, nor does it incorporate any of the terms of that agreement.  Instead, it

merely acknowledges the existence of the settlement that precipitated the

dismissal.8

  The parties’ settlement agreement, in turn, says nothing about the

8

  Although Kokkonen “does not state how a district court may incorporate a

settlement agreement in a dismissal order, the case does suggest the agreement

must be ‘embodied’ in the dismissal order.”  Schaefer Fan Co. v. J & D Mfg., 265

F.3d 1282, 1286 (Fed. Cir. 2001) (quoting Miener v. Mo. Dep’t of Mental Health, 62

F.3d 1126, 1128 (8th Cir. 1995)).  At least one court has suggested that the full text

of the settlement agreement should be included in the order of dismissal to

13
district court retaining jurisdiction to adjudicate disputes arising out of the

agreement.9

  These circumstances are insufficient to confer ancillary jurisdiction

on the district court to adjudicate what remains a state law contract claim.  See,

e.g., Scelsa v. City Univ. of New York, 76 F.3d 37, 41 (2d Cir. 1996); see also In re

Phar‐Mor, Inc. Sec. Litig., 172 F.3d 270, 274 (3d Cir. 1999) (“The phrase ‘pursuant

to the terms of the Settlement’ [in dismissal order] fails to incorporate the terms

of the Settlement Agreement into the order because a dismissal order’s mere

reference to the fact of settlement does not incorporate the settlement agreement

in the dismissal order.”(internal quotation marks and alteration omitted)).  

In opposition, StreetEasy argues that the actions of Chertok and the district

court confirm that the settlement was incorporated into the dismissal order.  In

particular, StreetEasy points out that Chertok himself repeatedly asked the

constitute incorporation, Bd. of Trs. v. Madison Hotel, Inc., 97 F.3d 1479, 1484 n.8

(D.C. Cir. 1996), and another has indicated that physical attachment of a

settlement agreement to a dismissal order would not be enough, Hospitality

House, Inc. v. Gilbert, 298 F.3d 424, 431 (5th Cir. 2002).  We need not define the

full range of circumstances that would constitute “incorporation” of a

settlement’s terms for purposes of conferring ancillary jurisdiction on a district

court.  

9

  Appellee cites cases in which dismissal was entered “pursuant to” settlement

agreements expressly providing that federal courts would retain jurisdiction over

settlement‐related disputes.  No such provisions are implicated here.  See, e.g.,

Schaefer Fan Co., 265 F.3d at 1286‐87; Interspiro USA, Inc. v. Figgie Int’l Inc., 18

F.3d 927, 930 (Fed. Cir. 1994).  

14
district court to enforce the settlement agreement, that the magistrate judge

indicated that he would retain a copy of the settlement transcript in his

chambers’ file, and that the district court plainly thought it had jurisdiction to

enforce the agreement because it entered the enforcement order.  These

arguments are unpersuasive.  The order of dismissal unambiguously omits to

retain jurisdiction or to incorporate the terms of the settlement.  After‐the‐fact

statements and actions of the parties, and even of the district court, cannot create

ancillary jurisdiction where such jurisdiction was not retained upon dismissal.10

Cf. Williams v. United States, 947 F.2d 37, 39 (2d Cir. 1991) (“[S]ubject matter

jurisdiction may not be created by estoppel or consent of the parties.”); see also In

re Phar‐Mor, Inc. Sec. Litig., 172 F.3d at 275 (“[U]nder Kokkonen, unexpressed

intent is insufficient to confer subject matter jurisdiction.”).  

In sum, as in Kokkonen, “the only order here was that the suit be

dismissed, a disposition that is no way flouted or imperiled by the alleged breach

of the settlement agreement.” See Kokkonen, 511 U.S. at 380.  Because the district

court lacked ancillary jurisdiction or any other basis for jurisdiction over

10  Nor does the magistrate judge’s indication that he would keep a copy of the

settlement in his chambers’ file manifest the judge’s intent to retain jurisdiction

over the enforcement of the settlement.  In context, the statement simply assured

the parties that the settlement would be kept confidential.  

15
appellee’s motion to enforce the settlement agreement, we vacate the district

court’s orders enforcing the settlement agreement and holding Chertok in

contempt for noncompliance.11  See Willy v. Coastal Corp., 503 U.S. 131, 139

(1992) (“Given that civil contempt is designed to coerce compliance with the

court’s decree, it is logical that the order itself should fall with a showing that the

court was without authority to enter the decree.”); Tekkno Labs., Inc. v. Perales,

933 F.2d 1093, 1099 (2d Cir. 1991) (“Where a federal court lacks subject matter

jurisdiction to grant a particular type of injunction, it also lacks the power to issue

a civil contempt order for noncompliance with that injunction.”).                 

II. Rule 11 Sanctions

We review a district court’s imposition of sanctions under Federal Rule of

Civil Procedure 11 for abuse of discretion, “mindful that a material error of law

or a clearly erroneous assessment of evidence is an abuse of discretion.”

11  After the district court ordered enforcement of the settlement agreement,

Chertok took steps to comply.  For instance, he delivered signed copies of certain

transaction documents to StreetEasy and — after the district court held him in

contempt — executed a mutual release.  Chertok asks us to declare these actions

void.  We will not do so.  Chertok points to no legal authority that obliges us to

adjudicate the legal effect that the district court’s unauthorized orders have on

actions taken by Chertok consistent with the settlement agreement.  If Chertok

wishes to further litigate the legal effect of actions taken in furtherance of the

settlement agreement, the proper forum, as he has correctly insisted, is the state

court.

16
Derechin v. State Univ. of New York, 963 F.2d 513, 516 (2d Cir. 1992) (internal

quotation marks omitted).  Under Rule 11(b), an unrepresented party who

presents a written motion to the court certifies that:

(1) [the motion] is not being presented for any improper

purpose, such as to harass, cause unnecessary delay, or

needlessly increase the cost of litigation;

(2) the claims, defenses, and other legal contentions are

warranted by existing law or by a nonfrivolous

argument for extending, modifying, or reversing

existing law or for establishing new law;

(3) the factual contentions have evidentiary support or,

if specifically so identified, will likely have evidentiary

support after a reasonable opportunity for further

investigation or discovery; and

(4) the denials of factual contentions are warranted on

the evidence or, if specifically so identified, are

reasonably based on belief or a lack of information.

Fed. R. Civ. P. 11(b).  A false certification violates Rule 11(b), and the district

court has discretion to impose sanctions to “deter repetition of the conduct or

comparable conduct by others similarly situated.”  Id. 11(c)(4).  When sanctions

are imposed on motion of an adversary, “[t]he standard for triggering the award

of fees under Rule 11 is objective unreasonableness and is not based on the

subjective beliefs of the person making the statement.”  Star Mark Mgmt., Inc. v.

Koon Chun Hing Kee Soy & Sauce Factory, Ltd., 682 F.3d 170, 177 (2d Cir. 2012)

(internal quotation marks omitted).  With respect to factual contentions,

17
“sanctions may not be imposed unless a particular allegation is utterly lacking in

support.”  Storey v. Cello Holdings, L.L.C, 347 F.3d 370, 388 (2d Cir. 2003)

(internal quotation marks omitted).     

On StreetEasy’s motion, the district court sanctioned Chertok pursuant to

Rule 11 for propounding unsupported factual contentions in his submissions and

oral representations to the court.  In particular, the district court identified three

sanctionable instances: (1) Chertok “claimed to have had no notice of the Backup

and Compliance Certificates, despite admitting to having received copies of those

certificates as email attachments”; (2) Chertok willfully ignored plain language in

the Settlement requiring him to sign “the action by written consent dated as of

August 30, 2006 in order to argue that he was not obligated to sign such a form”;

and (3) Chertok misrepresented that the parties’ settlement was non‐binding

even though Magistrate Judge Peck stated unequivocally that the settlement

agreement would be binding even without a written agreement.  We consider

each of these instances in turn.  We share the district court’s desire to check

Chertok’s less‐than‐straightforward conduct, but for the following reasons we

conclude that the district court erred in sanctioning Chertok on the basis of two

of the identified instances.  We also conclude, however, that the district court

18
acted within its discretion in sanctioning Chertok for his misrepresentation of

what documents he agreed to sign pursuant to the settlement agreement.

Accordingly, we vacate the district court’s award of sanctions and remand the

matter for reconsideration of the appropriate sanction amount in light of this

decision.  

A. Notice of the Backup and Compliance Certificates

In August and September 2006, in connection with the Series A Stock Sale,

Smith sent Chertok a number of documents and signature pages to sign.  In

response, Chertok requested to see certain documents before signing the

signature pages.  On September 9 and 11, Smith sent Chertok most of these

documents as email attachments.  Among the attached documents were a

Compliance Certificate and a Backup Certificate.12  It is undisputed that the

12  The Backup Certificate is a document addressed to Proskauer to assist the firm

in its preparation of a legal opinion regarding the Series A Stock Sale.  It

represents to Proskauer, among other things, that the Written Consent in Lieu of

a Special Meeting of the Board of Directors dated August 30, 2006 is “true,

complete and correct.”  Chertok claims that the Backup Certificate’s

representation was false because he had not signed the written consent. The

Compliance Certificate is a document that was to be delivered to Series A Stock

purchasers stating that StreetEasy had performed its obligations under the Stock

Purchase Agreement, which included delivering the Proskauer Opinion to all

Series A Stock purchasers.  Chertok claims the Compliance Certificate’s

representation was false because his company — Vast Ventures — was a Series A

Stock purchaser, but he never received a copy of the Proskauer Opinion until

19
versions of these certificates that Chertok received in 2006 were unexecuted.

Following the parties’ settlement, StreetEasy forwarded partially executed

versions of the Compliance and Backup Certificates to Chertok.  These versions

of the certificates reflected the fact that Smith had already signed the certificates

as of August 31, 2006 — days before Smith emailed the unexecuted versions of

these certificates to Chertok in September 2006.  Based on these circumstances,

Chertok argued to the district court that Smith purposely concealed the executed

versions from him in furtherance of Smith’s scheme to usurp control of the

company.  In his Rule 60(b) motion, Chertok stated that he saw the executed

signature pages of these certificates for the first time post‐settlement and was not

previously aware of their existence.  He further argued that “[h]ad [he] known

the Backup Certificate or Compliance Certificate were [sic] executed, [he] would

not have settled,” and that the settlement should therefore be rescinded.    

The district court sanctioned Chertok for claiming to have had no notice of

the Backup and Compliance Certificates, despite admitting having received

copies of those certificates as email attachments in 2006.  In other words, the

district court concluded that Chertok represented that he had no notice of the

after he settled with StreetEasy in 2012.  

20
Backup and Compliance Certificates and that this representation was utterly

lacking in support.  That conclusion is erroneous.  Chertok never represented that

he lacked notice of the existence of the Backup and Compliance Certificates.

Instead, Chertok consistently represented that he lacked notice of the executed or

signed versions of these certificates.  

Although the district court correctly concluded that Chertok’s alleged

unawareness of the executed versions of the certificates did not warrant Rule

60(b) relief, the standards for Rule 60(b) relief and Rule 11 sanctions are not the

same.  That the failure to provide Chertok with executed copies of the documents

did not entitle Chertok to Rule 60(b) relief does not mean that Chertok’s claim not

to have received such copies was factually false.  In order for a factual contention

to be sanctionable under Rule 11, it must be utterly lacking in support.  Kiobel v.

Millson, 592 F.3d 78, 81 (2d Cir. 2010).  In this case, Chertok sufficiently

supported his contention that he was unaware that Smith had executed the

Backup and Compliance Certificates until he received the executed versions of

those certificates post‐settlement.13  Because the district court’s sanction award

13  Because the district court sanctioned Chertok for making unsupported factual

contentions, we need not consider whether Chertok’s attempt to obtain Rule

60(b) relief on this basis constituted a legally frivolous argument.

21
rested on a clearly erroneous assessment of the evidence, it must be vacated to

the extent it is founded on Chertok’s supposed misrepresentation regarding the

Backup and Compliance Certificates.   

B. Action by Written Consent dated August 30, 2006

The district court also sanctioned Chertok for willfully ignoring the plain

language of the settlement in arguing that he was not obligated to sign an action

by written consent dated August 30, 2006.  In the parties’ settlement agreement,

Chertok “ratifie[d] and consent[ed] to the actions taken at the August 29, 2006

board and shareholder meetings and [agreed to] sign any and all documents

required by that, including the action by written consent dated as of August 30,

2006.”  A few days after StreetEasy’s suit was dismissed, StreetEasy forwarded

two written consents dated August 30, 2006 for Chertok’s signature.  Chertok

refused to execute those consents and in his Rule 60(b) motion he argued that the

settlement did not require him to execute either of them because the settlement

did not “contemplate that he was to consent to meetings which [StreetEasy]

alleged never took place.”  J.A. 75 (emphasis omitted).

The district court did not abuse its discretion in sanctioning Chertok for his

mischaracterization of the parties’ settlement.  Chertok’s contention that the

22
settlement agreement did not require him to execute either of these documents is

flatly contradicted by the record.  In the agreement, Chertok expressly agreed to

execute an action by written consent dated August 30, 2006.  He offers no logical

reason to believe that neither of the documents proffered by StreetEasy

constituted the action by written consent that he agreed to execute.14  On appeal,

Chertok argues that he believed the consent described in the settlement referred

to a document labeled Exhibit A in the minutes of an August 29, 2006 board

meeting, and that Exhibit A was a different written consent from the ones

StreetEasy requested he execute after the settlement.15  Chertok’s asserted belief is

objectively unreasonable.  Chertok offers no evidence that the consent referenced

in the board minutes is meaningfully different from the consents presented for

his signature post‐settlement.  Moreover, although he claims that he could not

have guessed that StreetEasy would ask him to execute the shareholder and

14  Although the settlement transcript referred to the action by written consent

dated August 30, 2006, in the singular, this does not assist Chertok, as he

represented that the settlement agreement did not obligate him to execute either

of the written consents dated August 30, 2006.

15  Confusingly, Chertok claims that Exhibit A referenced in the board minutes

does not exist and that its nonexistence somehow strengthens his contention that

Exhibit A was the consent described in the settlement.  Chertok’s insistence that

the parties agreed to execute a nonexistent written consent merely serves to

highlight the objective unreasonableness of his contentions.

23
board written consents dated August 30, 2006, his proclaimed belief is not

credible.  Indeed, he admits that Smith sent him these written consents and asked

him to sign them as early as September 2006.  Under the circumstances, we

conclude that the district court did not abuse its discretion in sanctioning Chertok

for his mischaracterization of the parties’ settlement agreement.  

C. Binding Nature of Settlement Agreement

Finally, the district court sanctioned Chertok for representing that the

parties’ settlement was nonbinding absent a writing even though Magistrate

Judge Peck stated unequivocally that the recorded transcript of the parties’

settlement would itself constitute a binding settlement agreement and no formal

writing would be necessary.  During the parties’ settlement conference, Judge

Peck described the material terms of the settlement on the record.  At no point

did Judge Peck state that the settlement agreement would be non‐binding absent

a writing, and indeed he indicated the exact opposite.  Following Judge Peck’s

description of the terms of the settlement, Chertok and Smith (on behalf of

StreetEasy) expressly confirmed their agreement.  Neither party indicated that

the agreement would only take effect upon execution of a written document.

Despite the fact that the parties’ agreement did not expressly state that it would

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only become binding upon incorporation in a written document, during oral

argument for Chertok’s Rule 60(b) motion, Chertok represented to the district

court that the parties’ settlement was “not binding absent a writing because

[StreetEasy] expressed its intent not to be bound in the release” it forwarded to

Chertok for his signature post‐settlement, and because “the record contemplates

a writing.”

Chertok argues that the district court abused its discretion in sanctioning

him for this statement because it was not utterly lacking in factual support and

because he did not receive notice that this statement allegedly violated Rule

11(b).  We agree that Chertok did not receive adequate notice that his

representation about the non‐binding nature of the parties’ settlement would

expose him to sanctions, and we therefore do not decide whether his statement

constituted an unfounded factual assertion.16  

16  Although the district court construed Chertok’s statement as a factual

representation about whether a written document was an express condition

precedent to the formation of the parties’ agreement, it can also be understood as

a legal argument about whether the agreement would be binding under New

York law or federal common law in light of the fact that some of the terms of the

mutual release which the parties agreed to execute as part of the settlement were

not fully described on the record.  See Ciaramella v. Reader’s Digest Ass’n, Inc.,

131 F.3d 320, 322, 326 (2d Cir. 1997); Velazquez v. St. Barnabas Hosp., 13 N.Y.3d

894, 895 (2009).  Because the district court’s decision to sanction Chertok for this

representation cannot be upheld due to lack of notice, we need not decide

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In accordance with principles of due process and Rule 11 itself, the subject

of a sanctions motion “must receive specific notice of the conduct alleged to be

sanctionable and the standard by which the conduct will be assessed, and an

opportunity to be heard on that matter.”  Ted Lapidus, S.A. v. Vann, 112 F.3d 91,

97 (2d Cir. 1997); see also Fed. R. Civ. P. 11(c).  “Only conduct explicitly referred

to in the instrument providing notice is sanctionable.”  Star Mark Mgmt., Inc., 682

F.3d at 175 (internal quotation marks omitted).  In this case, Chertok received

neither a notice that the district court considered his representation sanctionable

nor an opportunity to explain why he should not be sanctioned for the

representation.  Chertok made the sanctioned representation during the oral

argument for his Rule 60(b) motion.  Although the district judge expressed

skepticism about the validity of Chertok’s argument that the settlement

agreement was nonbinding, he at no point indicated that Chertok risked

sanctions by continuing to press it.  Furthermore, StreetEasy’s Rule 11 motion —

the instrument by which Chertok received notice of his sanctionable conduct —

did not identify this specific representation, or even Chertok’s general argument

whether the district court properly construed Chertok’s statement as a factual

misrepresentation or whether Chertok’s statement could be sanctioned as a

legally frivolous argument.  

 

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about the non‐binding nature of the parties’ settlement, as sanctionable conduct.

By sanctioning Chertok for conduct beyond that specified in StreetEasy’s motion,

the district court failed to afford him the notice and opportunity to be heard

required by due process and Rule 11.  See Ted Lapidus, S.A., 112 F.3d at 97

(sanctions vacated where district court sanctioned conduct “beyond the conduct

specified in [adversary’s] Rule 11 motion”).17  Accordingly, the district court’s

order awarding sanctions must be vacated insofar as it relied on Chertok’s

representation about the nonbinding nature of the parties’ settlement agreement.

CONCLUSION

For the foregoing reasons, the district court’s orders enforcing the parties’

settlement agreement and holding the defendant in contempt for noncompliance

are VACATED.  The district court’s order awarding sanctions is VACATED.  The

order setting the amount of fees and costs awarded to the plaintiff is VACATED

and this matter is REMANDED for reconsideration of the appropriate amount of

monetary sanctions in light of this decision.  

17  Even when a district court initiates sanctions sua sponte, it must enter an order

directing the party “to show cause why conduct specifically described in the

order has not violated Rule 11(b).”  Fed. R. Civ. P. 11(c)(3); see also In re Pennie &

Edmonds LLP, 323 F.3d 86, 89 (2d Cir. 2003).  The district court entered no such

order here.

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