DANA M. CHILES, Trustee v. THOMAS W. LITTAUER.

NOTICE: Summary decisions issued by the Appeals Court pursuant to M.A.C. Rule
23.0, as appearing in 97 Mass. App. Ct. 1017 (2020) (formerly known as rule 1:28,
as amended by 73 Mass. App. Ct. 1001 [2009]), are primarily directed to the parties
and, therefore, may not fully address the facts of the case or the panel's
decisional rationale. Moreover, such decisions are not circulated to the entire
court and, therefore, represent only the views of the panel that decided the case.
A summary decision pursuant to rule 23.0 or rule 1:28 issued after February 25,
2008, may be cited for its persuasive value but, because of the limitations noted
above, not as binding precedent. See Chace v. Curran, 71 Mass. App. Ct. 258, 260
n.4 (2008).

COMMONWEALTH OF MASSACHUSETTS

APPEALS COURT

23-P-1056

DANA M. CHILES, trustee, 1

vs.

THOMAS W. LITTAUER.

MEMORANDUM AND ORDER PURSUANT TO RULE 23.0

The trustee, Dana M. Chiles, appeals from a Superior Court

judgment dismissing his first amended complaint (complaint),

both for lack of prosecution and as a sanction for what a judge

(first motion judge) concluded was a willful failure to provide

discovery. The defendant, Thomas W. Littauer, cross-appeals

from a second motion judge's order allowing the trustee's motion

for leave to file his notice of appeal late. Seeing no abuse of

discretion in the latter order, we conclude that the appeal is

properly before us. We are constrained to conclude, however,

that the first motion judge abused his discretion in dismissing

the complaint. We therefore vacate the judgment of dismissal.

1 Of the Brabern Realty Trust.
Background. The trustee's 2016 complaint asserted a claim

for wrongful foreclosure on a property where he operated a horse

stable business. The complaint included related claims for

damages based on theories such as defamation, fraud,

G. L. c. 93A, and interference with business relationships.

Littauer deposed the trustee and served requests for production

of documents. In response, the trustee produced a few

photographs but asserted that he did not possess any more

responsive documents. After Littauer filed a motion to compel,

a judge 2 ruled in 2018 that the trustee must produce responsive

documents within four weeks or else be precluded from

introducing them at the trial set for later that year. The

trustee produced no more documents.

After postponements of trial and further motion practice,

another judge ruled in 2019 that, because of the trustee's

"failure to produce documents after repeated offers and

requests, the [trustee] is precluded from entering any documents

at trial (with the exception of photographs he has produced)

that support any and all claims for damages."

After the trial was further delayed, a judge entered

partial summary judgment concluding that Littauer had wrongfully

2 With the exception of the two motion judges whose rulings
are directly at issue on appeal, we do not differentiate between
the many judges who ruled on motions during the long history of
this case.

2
foreclosed on the property the trustee claimed to own. The

trustee continued to pursue his damages claims.

In June 2022, Littauer, asserting that the trustee still

had not produced any more documents, moved in limine to preclude

the trustee from introducing any documents at the impending

trial. In November 2022, when the trustee's then-counsel was

experiencing medical issues, a judge ordered the trustee either

to ensure then-counsel was ready for trial in March 2023 or to

have a successor file a notice of appearance by February 1,

2023, and be prepared for trial in March 2023. Then-counsel

moved to withdraw, but the trustee failed to have new counsel

file a notice of appearance by February 1.

In response, on March 20, 2023, a judge allowed then-

counsel to withdraw and ordered the trustee to have new counsel

appear, and "to file any opposition" to Littauer's still-pending

motion in limine, by April 28, 2023. The judge's order stated,

"If there has been no notice of appearance filed by successor

counsel on or before April 28, 2023, and/or no opposition to the

motion in limine, this matter shall be dismissed for lack of

prosecution." The judge ordered the trustee not to treat this

warning "with the same indifference" as the trustee had

displayed in response to the November 2022 order.

New counsel for the trustee filed his appearance by the

April 28, 2023 deadline, but he did not file a response to the

3
motion in limine until a week later, on May 5, 2023. In the

response, the trustee asserted that counsel had read the March

20, 2023 order and concluded that he need not file an opposition

to the motion in limine, for two reasons. First, he viewed the

motion as moot, because two previous judges had already

precluded the trustee from offering documents at trial if not

produced in discovery. Second, he asserted that no further

documents were necessary to prove the trustee's damages; the

trustee would do so based on trial testimony.

Littauer then filed a reply memorandum in which he asserted

three grounds to dismiss the trustee's remaining claims. These

were, first, that the trustee's failure to file an opposition to

the motion in limine was a violation of the March 20, 2023

order, which had warned that noncompliance would lead to

dismissal for lack of prosecution. Second, dismissal was

warranted as a discovery sanction, for failure to comply with

prior orders to produce documents. Third, the trustee could not

prove damages by relying only on witness testimony, and

therefore a trial would be a waste of judicial resources.

After a hearing, the first motion judge ordered the

trustee's remaining claims dismissed, both for lack of

prosecution and as a sanction for what the judge termed the

trustee's "willful failure to provide discovery and comply with

4
court orders." On May 18, 2023, a judgment entered dismissing

the complaint in its entirety. 3

The trustee then prepared a notice of appeal, which was

dated May 31, 2023, and to which he attached a certificate of

electronic service bearing the same date. But, the Superior

Court clerk's office did not receive the notice of appeal by the

applicable deadline, June 19, 2023. Learning of this, the

trustee filed a motion for leave to file a late notice of

appeal, asserting that the delay was the result of excusable

neglect within the meaning of Mass. R. A. P. 4 (c), as appearing

in 481 Mass. 1606 (2019). Specifically, counsel asserted that

"due to some computer glitch the notice of appeal got sent to

his [d]rafts folder on [the court's electronic filing website]

instead of being timely filed." A second motion judge allowed

the motion, and the trustee filed his notice of appeal on July

6, 2023.

Littauer then cross-appealed from the order allowing the

motion and also sought reconsideration, asserting that the

trustee had failed to show excusable neglect. The trustee

opposed reconsideration and filed an affidavit of counsel

further explaining his belief that the late filing resulted from

3 Because we vacate the judgment in any event, we need not
address whether its scope was erroneously broader than that of
the order of dismissal.

5
an error in the electronic filing system rather than his own

negligence. The second motion judge denied reconsideration.

Discussion. 1. Trustee's late notice of appeal. To

determine whether the trustee's appeal is properly before us, we

must turn first to Littauer's cross appeal. Littauer argues

that the second motion judge abused his discretion in allowing

the trustee to file a late notice of appeal. See Mass. R. A.

P. 4 (c), as appearing in 481 Mass. 1606 (2019) (on showing of

excusable neglect, trial court may extend time for filing notice

of appeal for period not to exceed thirty days from original

deadline); Adoption of Patty, 489 Mass. 630, 636 n.9 (2022)

(judge's decision under rule 4 (c) reviewable for abuse of

discretion). The excusable neglect standard looks to

"circumstances that are unique or extraordinary" and is not

extended "to cover any kind of garden-variety oversight"

(citations and quotations omitted). Bernard v. United Brands

Co., 27 Mass. App. Ct. 415, 418 n.8 (1989). An abuse of

discretion is a "clear error of judgment in weighing the factors

relevant to the decision . . . such that the decision falls

outside the range of reasonable alternatives." L.L. v.

Commonwealth, 470 Mass. 169, 185 n.27 (2014) (quotation

omitted).

We see no abuse of discretion here. The second motion

judge reasonably could have credited the trustee's counsel's

6
assertions that he attempted to file the notice of appeal on May

31, 2023, which would have been timely. Counsel asserted that,

as he discovered only later, the filing remained in the

"[d]rafts" folder of his electronic filing system account -- a

problem he had never experienced before. These assertions were

supported by the dates on the notice of appeal and certificate

of service, by counsel's later affidavit, and by the undisputed

fact that counsel ordered transcripts for the appeal that same

day, May 31, 2023.

That counsel did not initially support his motion with an

affidavit was not fatal. Counsel's later-filed affidavit

explained that he had filed the motion, inferably in haste, on

the same day as he learned that the clerk had not received his

notice of appeal. Although, as Littauer argues, counsel

apparently failed to realize that he had not received a filing

confirmation e-mail on the day he believed he had filed the

notice of appeal, counsel explained he had received two other

filing confirmations that same day, related to this same case,

and may have confused them with the confirmation relating to the

notice of appeal.

Littauer also points to another court's decision, on quite

different facts, that failure to note the absence of a filing

confirmation email was inconsistent with excusable neglect. See

Ragguette v. Premier Wines & Spirits, 691 F.3d 315, 329 (3d Cir.

7
2012). But that does not establish any abuse of discretion

here. Cf. L.L., 470 Mass. at 185 n.27 (decision not abuse of

discretion simply because reviewing court would have reached

different result). Rule 4 (c) does not require that the late-

filing party be completely blameless, but only that any neglect

be excusable. The second motion judge did not abuse his

discretion in concluding that the standard was met here. The

trustee's appeal is thus properly before us.

2. Dismissal for lack of prosecution. "On motion of the

defendant, with notice, the court may, in its discretion,

dismiss any action for failure of the plaintiff to prosecute or

to comply with these rules or any order of court." Mass. R.

Civ. P. 41 (b) (2), 365 Mass. 804 (1974). The trustee argues

that the first motion judge abused his discretion in dismissing

the trustee's remaining claims for failure to prosecute. See

Monahan v. Washburn, 400 Mass. 126, 128 (1987) (dismissal for

lack of prosecution reviewed for abuse of discretion).

Specifically, the trustee asserts that it was an abuse of

discretion for the judge to rely on the trustee's failure to

file an opposition to Littauer's motion in limine by April 28,

2023, because the order setting that deadline was unclear.

Although the first motion judge was understandably concerned

that the case was still unresolved "more than five years past

the originally scheduled trial date," we agree with the trustee

8
that dismissal for lack of prosecution was improper in these

circumstances. 4

A dismissal for lack of prosecution "is a drastic sanction

which should be utilized only in extreme situations." Monahan,

400 Mass. at 128. "As a minimal requirement, there must be

convincing evidence of unreasonable conduct or delay. A judge

should also give sufficient consideration to the prejudice that

the movant would incur if the motion were denied, and whether

there are more suitable, alternative penalties." Id. at 128-

129.

Here, the order setting the deadline contained two

imprecise phrases regarding the filing of an opposition, such

that the trustee's failure to file one was not "convincing

evidence of unreasonable conduct or delay." Monahan, 400 Mass.

at 128. First, the order required the trustee "to file any

opposition" to the motion by April 28, 2023. The phrase "any

opposition" clearly implies that there may be no opposition at

all. A party is not ordinarily required to oppose a motion and

may reasonably choose not to do so if, for example, the party is

We focus on the specific conduct -- failure to file an
4

opposition to the motion in limine -- that the first motion
judge considered as the basis for dismissal for lack of
prosecution. Whether the trustee in fact engaged in any
unreasonable conduct or delay earlier in the case, or for that
matter violated "any order of court" earlier in the case that
might have warranted dismissal for lack of prosecution, see rule
41 (b) (2), is not before us.

9
indifferent to whether the motion is allowed. Here, if the

judge who issued the order setting the deadline meant to require

the trustee to file a statement of his position on the motion

(whatever it might be), then an order to file "any opposition"

by a certain date was not a clear way to do so.

Second, the order setting the deadline stated, "If there

has been no notice of appearance filed by successor counsel on

or before April 28, 2023, and/or no opposition to the motion in

limine, this matter shall be dismissed for lack of prosecution."

The term "and/or" is a "vague expression," and its use may

"make[] it impossible to discover" the meaning of the sentence

in which it is used. Hanson v. Bradley, 298 Mass. 371, 378

(1937). "[T]he use of the phrase 'and/or' creates ambiguity."

Matter of the Colecchia Family Irrevocable Trust, 100 Mass. App.

Ct. 504, 514 (2021). Here, the trustee reasonably could have

understood, as he asserted he did, that to avoid a dismissal for

lack of prosecution, it was sufficient for counsel to file a

notice of appearance by the deadline; he need not also file an

opposition to the motion in limine.

Further, the failure to file an opposition caused no

unreasonable delay, where the first motion judge could simply

have allowed the motion in limine once the opposition deadline

passed. And once the trustee did file what he styled an

"opposition," one week after the April 28, 2023 deadline, his

10
position was that the motion was moot because "the precise

relief" it sought had already been granted by two earlier

orders. Regardless whether that assessment was correct, 5 the

trustee's filing still left the judge with the option to allow

the motion in limine and proceed to trial, based on the

trustee's representation that he stood "ready to try [the] case

as scheduled" and would rely on oral testimony to attempt to

prove his damages.

Because "convincing evidence of unreasonable conduct or

delay" is the "minimal requirement" for a dismissal for lack of

prosecution, Monahan, 400 Mass. at 128, but is absent here, we

need not consider the remaining factors at any length. It is

enough to say, regarding "the prejudice that the movant would

incur if the motion [to dismiss] were denied," id., that the

unfair prejudice Littauer faced from the trustee's failure to

oppose the motion in limine (or his one week delay in opposing

it) was virtually nonexistent. Littauer had already obtained

orders barring the trustee from introducing at trial any

5 The two prior orders differed in scope, but each appeared
to leave room for the trustee to introduce some documents at
trial. Littauer's motion in limine, however, sought to preclude
the trustee from introducing any documents whatsoever at trial.
The trustee, while professing to believe that that relief had
already been granted, maintained in his opposition that he could
still "introduce documents filed or obtained via subpoena, and
record documents." We need not address that issue. For
purposes of this appeal, we assume that the trustee's only
evidence of damages was and is witness testimony.

11
documents bearing on damages that had not already been produced.

The absence of an opposition from the trustee in no way delayed

the first motion judge from allowing the motion in limine, to

whatever extent it was not moot. And the "more suitable,

alternative penalt[y]" for the trustee's failure to file an

opposition to Littauer's motion in limine, id. at 129, would

have been merely to allow the motion. We conclude that the

dismissal for lack of prosecution was an abuse of discretion.

3. Dismissal as a discovery sanction. Where "a party

fails to obey an order to provide or permit discovery," a judge

may impose sanctions up to and including "dismissing the

action." Mass. R. Civ. P. 37 (b) (2) (C), as amended, 390 Mass.

1208 (1984). Such dismissal is an "extreme sanction," which

generally must be "predicated on a finding of wilfulness or bad

faith." Keene v. Brigham & Women's Hosp., Inc., 439 Mass. 223,

236 (2003). Here, the first motion judge concluded that the

trustee's failure to "provide[] any documentary evidence

supporting his claims" was a "willful failure to provide

discovery" that warranted dismissal. 6 Reviewing the order for

abuse of discretion, see Solimene v. B. Grauel & Co., 399 Mass.

6 To whatever extent the judge may have viewed the failure
to file any opposition to the motion in limine by April 28,
2023, as another discovery violation, dismissal on that basis
was an abuse of discretion, for the reasons already explained
and also because the order to file an opposition was not "an
order to provide or permit discovery." Rule 37 (b) (2) (C).

12
790, 799 (1987), we are again constrained to conclude that

dismissal was not warranted.

The trustee consistently asserted that he had produced all

responsive documents in his possession, custody, or control; he

claimed that other documents had been lost when a separate

property owned by the trustee was foreclosed upon. The trustee

argued that he "can't produce documents he doesn't have."

Littauer did not challenge this assertion as untrue, 7 nor did any

of the judges who ruled on earlier motions to compel find it to

be untrue. Rather, Littauer sought, and obtained, orders

precluding the trustee from relying at trial on any documents

not produced by a particular date, or on any documents that

supported the trustee's damages claims. Littauer told one judge

that this preclusive remedy was "very fair."

As the court stated in Keene, "[r]equests for discovery

pursuant to Mass. R. Civ. P. 34 (a), 365 Mass. 792 (1974),

require production of documents that 'are in the possession,

custody or control of the party upon whom the request is

served.'" Keene, 439 Mass. at 233. Accordingly, "rule 34 (a)

does not demand production of documents that 'were in' or that

7 Littauer makes this claim for the first time in his
appellate brief, but he cites no evidence for his assertion.
Notably, at the trustee's 2018 deposition, Littauer failed to
question the trustee about his damages, let alone whether he had
documents to prove those damages.

13
'should have been kept in' the party's possession. Put simply,

there can be no discovery violation, and hence no rule 37

sanction, when a party fails to produce documents it does not

possess," id., or that are not in its custody or control.

Absent a finding that the trustee had responsive documents

in his possession, custody, or control that he had failed to

produce, there was no basis to find a violation of a discovery

order, let alone the willful violation that would be required to

justify dismissal. The Supreme Judicial Court has said that

such a finding, whether explicit or implicit, is necessary and

must be supportable:

"Since due process requirements may limit the sanction of
dismissal, where there is an inability to comply, we
conclude that it is necessary for an appellate court to
know if the judge's action was predicated on a finding of
wilfulness, bad faith, or fault, unless it is clear that
such a determination was implicit and warranted" (emphasis
added; footnote omitted).

Gos v. Brownstein, 403 Mass. 252, 257 (1988). To whatever

extent the judge's reference to the trustee's "willful failure

to provide discovery" included an implicit finding that the

trustee possessed responsive documents, Littauer has pointed to

no evidence in the record supporting such a finding. See

DiGiovanni v. Board of Appeals of Rockport, 19 Mass. App. Ct.

339, 343 (1985) (finding clearly erroneous when there is no

evidence to support it). Because there was no supportable

14
finding of a discovery violation, dismissal as a discovery

sanction was an abuse of discretion.

Littauer's reliance on Maywood Bldrs. Supply Co. v. Kaplan,

22 Mass. App. Ct. 944 (1986) is misplaced. There, this court

affirmed dismissal of an action as a sanction for "a pattern of

persistent failure to comply with discovery orders." Id. at

944. The court acknowledged that the sanction was "severe, but

it followed only after several efforts to flush out documentary

material fundamental to the proof of the case. If that material

did not come forward, there was no point in letting the comedy

go on." Id. at 945. The court rejected the plaintiffs'

argument that dismissal was inappropriate without a finding that

the violations were willful. Id. Two years later, however, the

Supreme Judicial Court held the contrary. See Gos, 403 Mass. at

257 (dismissal as discovery sanction inappropriate absent

finding of willfulness, bad faith, or fault). Maywood Bldrs.

Supply Co. is thus no longer authoritative.

Littauer is also mistaken in suggesting that we affirm the

judgment of dismissal on the alternate ground relied on in

Keene, 439 Mass. at 237. There, the court recognized that a

party's failure to produce documents may give rise to an

inference that the documents would have contained proof adverse

to that party's case, sufficient to support ruling against that

party on liability as a matter of law. See id. But Keene was

15
an "exceptional" case, id., in which, among other distinguishing

circumstances, a trial court judge found that the defendant

hospital's failure to preserve medical records, as required by

statute, constituted spoliation; was the result of "at least

negligence"; and was an actionable form of medical malpractice.

Id. at 234-236. No comparable finding of fault was made here.

Whether such a finding could have been made, or could still be

made, is not before us. 8

4. Dismissal for lack of evidence. Finally, Littauer asks

us to affirm on the alternate ground that as a matter of law,

without the documents Littauer requested in discovery, the

trustee cannot prove any damages, and thus his remaining claims

should be dismissed without a trial. No doubt, "[w]hile it is

8 We do not mean to suggest that either the judge or
Littauer was required to accept the trustee's representation
that no documents regarding his damages claim were within his
possession, custody, or control. Indeed, in the joint pretrial
memorandum dated November 12, 2021, the trustee asserted that
his damages were based upon, among other things, lost profits
and customer good will, in a precise amount of $449,652.15. Yet
the trustee claimed below, and continues to claim, that he has
no documents in his possession, custody, or control that bear on
the questions, for example, of what his profits were for the
business, including his revenues and expenses, or, what
customers he once had but allegedly lost.
However implausible the trustee's representations, the
problem with the record before us is that there was essentially
no further discovery or testimony on what documents existed
other than the request for documents, and thus there were no
facts established from which the judge could find that documents
had been willfully withheld.

16
true that a plaintiff need not prove damages with mathematical

certainty, 'damages cannot be recovered when they are remote,

speculative, hypothetical, and not within the realm of

reasonable certainty.'" Kitner v. CTW Transp., Inc., 53 Mass.

App. Ct. 741, 748 (2002), quoting Lowrie v. Castle, 225 Mass.

37, 51 (1916). But the cases Littauer relies upon do not

establish any broad rule that damages cannot be proven without

documents. 9 The trustee's testimony would have to be

sufficiently concrete to establish damages with reasonable

certainty, but the lack of documents is not an absolute bar to

recovery.

Although we may affirm "on any ground supported by the

record," Clair v. Clair, 464 Mass. 205, 214 (2013), quoting

Gabbidon v. King, 414 Mass. 685, 686 (1993), here the record is

not sufficient to conclude as a matter of law that the trustee

cannot prove any damages. Littauer did not depose the trustee

as to what his testimony would be as to damages. See note 7,

supra. Littauer could have moved for summary judgment, but did

not, on the ground that the trustee had no reasonable

expectation of proving damages, an essential element of his

case. See Kourouvacilis v. General Motors Corp., 410 Mass. 706,

9 Snelling & Snelling of Mass., Inc. v. Wall, 345 Mass. 634,
635-636 (1963); Quarterman v. Springfield, 91 Mass. App. Ct.
254, 261-262, cert. denied, 583 U.S. 1013 (2017); Tech Plus,
Inc. v. Ansel, 59 Mass. App. Ct. 12, 17-21 (2003).

17
716 (1991). The trustee then would have been required to put

forward "such facts as would be admissible in evidence," Mass.

R. Civ. P. 56 (e), 365 Mass. 824, 825 (1974) -- without

documents, per the prior orders -- and argue that those adduced

facts were sufficient to support a damages claim under the law.

Whether such a summary judgment motion would have succeeded, or

could succeed if on remand a judge allowed it to be filed, are

questions not before us.

Conclusion. We affirm the order granting leave to file a

late notice of appeal. The judgment is vacated, and the case is

remanded for further proceedings consistent with this memorandum

and order.

So ordered.

By the Court (Sacks,
Englander & Grant, JJ. 10),

Clerk

Entered: November 4, 2024.

10 The panelists are listed in order of seniority.

18