NOTICE: This opinion is subject to motions for reargument under V.R.A.P. 40 as well as formal 

revision before publication in the Vermont Reports. Readers are requested to notify the Reporter 

of Decisions by email at: JUD.Reporter@vermont.gov or by mail at: Vermont Supreme Court, 

109 State Street, Montpelier, Vermont 05609-0801, of any errors in order that corrections may 

be made before this opinion goes to press.

2016 VT 29

No. 2015-253

Synecology Partners, L3C Supreme Court

On Appeal from

 v. Superior Court, Chittenden Unit,

Civil Division

Business RunTime, Inc., et al. December Term, 2015

Helen M. Toor, J.

Lawrence Kenney, South Burlington, and Franklin Kochman, Burlington, for Plaintiff-Appellant.

Craig S. Nolan and Kevin A. Lumpkin of Sheehey Furlong & Behm P.C., Burlington, for

 Defendants-Appellees.

PRESENT: Reiber, C.J., Dooley, Skoglund, Robinson and Eaton, JJ.

¶ 1. EATON, J. In this dispute between two computer software companies, 

SynEcology Partners, L3C challenges the trial court’s order dismissing its complaint against 

Business RunTime, Inc. stemming from its failure to comply with Business RunTime’s 

discovery requests. For the reasons stated herein, we affirm.

¶ 2. In 2008, SynEcology’s founders, Edward Grossman and Jeanne Conde, sold the 

company’s assets to Lawrence Kenney. Grossman and Conde subsequently started a new 

software company, Business RunTime. In August 2011, SynEcology filed a civil complaint in 

Chittenden Superior Court against Business RunTime, Edward Grossman, Jeanne Conde, and 
2

two former SynEcology employees, Thomas Reynolds and Toby Leong, for alleged fraud, theft 

of intellectual property, industrial sabotage, computer crimes, burglary, larceny, willful breaches 

of nondisclosure and employee contracts, theft and disclosure of trade secrets, and tortious 

interference with contractual relations. What followed was a protracted discovery phase, 

culminating in Business RunTime’s motion for contempt, sanctions, and attorneys’ fees, filed on 

July 23, 2014, which ultimately resulted in dismissal of SynEcology’s complaint. 

¶ 3. On April 17, 2012, Business RunTime filed its first set of interrogatories and 

production requests, due May 17, 2012. Among other things, Business RunTime specifically 

requested all emails relevant to SynEcology’s claims.

1 On May 22, 2012, and again on June 1,

2012, Business RunTime made inquiries as to when it could expect a response to the production

request. On June 20, 2012, Business RunTime moved to compel SynEcology to respond to the 

interrogatories and production requests. The motion was granted on August 3, 2012. 

¶ 4. SynEcology filed its first set of responses on August 31, 2012, three months after 

the deadline for Business RunTime’s initial request. Those responses contained a CD with PDF

files purporting to include all relevant emails. Some of the emails were in chronological order,

although none were in native format2, appearing instead in list form with no indication as to 

where one email ended and another began. Although the PDF files included some emails from

Mr. Kenney’s work account (the Outlook account) and the inboxes of two SynEcology 

employees, there was only one email from the year 2010, and there were no emails from Mr. 

Kenney’s personal account (the Comcast account). In addition to filing its responses, 

 

1

 Business RunTime requested “all emails constituting, showing, referring, or relating to 

any of the allegations in the Complaint” and reserved “the right to request native electronic 

formats, with all metadata, of any emails that are produced.” 

2

 In the context of software applications, native format refers to the format in which the 

file was created. 
3

SynEcology objected to the production of some emails “as to attorney-client communication, 

communication with retained experts and spousal communications,” and indicated that 

“[w]ithout waiving the objection and subject to the objection,” it would “provide the emails 

requested, subject to a protective order.” 

¶ 5. On October 17, 2012, Business RunTime offered SynEcology a proposed 

protective order covering information and documents that genuinely fell within the scope of 

Vermont Rule of Civil Procedure 26(c)(7), but noted its skepticism that all of the materials 

withheld truly fell within the scope of the Rule and reserved the right to object to discovery 

materials designated as privileged. Business RunTime specifically requested the native 

electronic formats of the emails produced, including the complete email inboxes of Mr. Kenney 

and the two relevant SynEcology employees. 

¶ 6. On February 25, 2013, SynEcology signed the protective order. On March 1,

2013, nearly eleven months after the initial request, SynEcology responded to the remainder of 

Business RunTime’s requests, indicating that by the next week, it would “produce a CD with as 

many of the documents as [it] can assemble in native format. This will include all of the Outlook 

files.” 

¶ 7. Four months later, on June 5, 2013, SynEcology supplemented its discovery 

responses, providing a CD with emails from Mr. Kenney, Thomas Barkley, and Joseph Luo, but 

no emails from Mr. Kenney’s Comcast account, and no emails in native format. Eighty-six of 

the emails provided on June 5 were redacted on grounds of privilege. SynEcology indicated the 

date, time, sender, and recipient of the privileged emails, but provided no privilege log.

¶ 8. Following this supplemental response, Business RunTime made three separate

attempts to obtain the emails in native format, as well as the remainder of the emails dated 2010 
4

from Mr. Kenney’s Outlook account and all relevant emails from his Comcast account. These 

attempts, in December 2013, February 2014, and March 2014, proved fruitless. 

¶ 9. On March 4, 2014, nearly two years after its initial production request, Business 

RunTime filed a second motion to compel production. The trial court granted the motion on 

May 22, 2014, ordering SynEcology to produce, by July 1, 2014, all emails “constituting, 

showing, referring or relating to any of the allegations in the complaint” in native format, and a 

privilege log identifying emails withheld on the grounds of privilege. 

¶ 10. On July 3, 2014, SynEcology produced emails from Mr. Kenney’s and two other 

SynEcology employees’ Outlook accounts, including 1881 emails from 2010, but no emails from 

Mr. Kenney’s Comcast account and no privilege log. SynEcology provided no explanation as to 

why some of the 2010 emails were withheld in its initial production response—the number had 

risen from one email produced in August 2012 to 1881 emails produced in July 2014. 

¶ 11. Business RunTime made two further requests to SynEcology for supplemental 

production of emails from Mr. Kenney’s Comcast account and a privilege log. On July 25, 2014,

SynEcology responded to these requests, indicating that there were no relevant emails from Mr. 

Kenney’s Comcast account. Although SynEcology promised to provide a privilege log by the 

following week, in early August 2014 SynEcology indicated that it would send the requested 

emails without a privilege claim. SynEcology subsequently produced forty-eight of the eightysix emails previously claimed as privileged. 

¶ 12. On July 23, 2014, Business RunTime filed a motion for contempt and sanctions, 

seeking dismissal as a result of SynEcology’s continuing failure to produce all relevant emails 

from Mr. Kenney’s Comcast account and a privilege log. On August 13, 2014, SynEcology 

responded to the motion, insisting that it had turned over all of the documents available to 

establish its case and prove its damages. In addition, SynEcology asserted that Mr. Kenney’s 
5

Comcast account was duplicative of his Outlook account, and that it had provided all of the 

emails previously claimed as privileged. On September 10, 2014, SynEcology’s attorney, 

Jerome F. O’Neill, filed two additional documents with the trial court: a supplemental correction, 

acknowledging factual misrepresentations in their August 13 filing denying the existence of 

relevant emails in Mr. Kenney’s Comcast account, and a motion for leave to withdraw as 

counsel. A hearing on the pending motions was scheduled for September 29, 2014. 

¶ 13. At the hearing, the motion for leave to withdraw dominated the proceedings. 

Business RunTime stated once again, however, that by its motion, it was seeking dismissal, 

reiterating for the trial court the history of the protracted discovery process leading up to that 

hearing. Business RunTime also stated that, as a result of SynEcology’s persistent 

misrepresentation of the facts regarding discovery, Business RunTime had lost faith in 

SynEcology’s ability to comply truthfully with the discovery order. 

¶ 14. The trial court granted attorney O’Neill’s motion to withdraw and granted 

SynEcology additional time to obtain counsel and submit additional filings on the motion. On 

December 3, 2014, attorney John F. Evers appeared on behalf of SynEcology, and on December 

16, 2014, SynEcology filed its supplemental opposition to Business RunTime’s motion for

contempt and sanctions. In that supplemental opposition, SynEcology reiterated that previous 

statements concerning the relevance of emails in the Comcast account were incorrect and 

indicated an ongoing attempt to locate any such emails. SynEcology also indicated its intent to 

provide a privilege log. 

¶ 15. On December 30, 2014, SynEcology filed a discovery certificate, producing what 

it claimed to be all emails requested in April 2012. Specifically, SynEcology provided a CD 

containing nonprivileged emails from Mr. Kenney’s Comcast account and indicated that it 

would, at a later date, provide a privilege log identifying those emails from the Comcast account 
6

that were withheld under a claim of privilege. In its brief, SynEcology states that it produced, to 

the best of its knowledge, all emails required to be produced by the May 22, 2014 order, 

including the thirty-eight emails referenced in the contempt ruling. The record, however, does 

not reflect the number of emails produced, nor does it indicate the date, sender, recipient, 

contents, or subject lines of the emails included on the CD. Furthermore, there is no record that 

SynEcology produced a privilege log at any time following the December 30, 2014 discovery 

certificate concerning the emails that it was not producing under claim of privilege. 

¶ 16. On February 26, 2015, the trial court granted Business RunTime’s motion for 

contempt and sanctions, finding that SynEcology “failed to comply with the court’s May 2014 

order.” In reviewing the two-and-a-half year discovery process, the trial court noted 

SynEcology’s failure to explain the numerous discrepancies in its responses to production 

requests, including the production of 1880 additional emails from 2010, the intentional

misrepresentation as to the existence of relevant emails from Mr. Kenney’s Comcast account, 

and the failure to produce a privilege log, which had yet to be produced as of February 2015. 

For these reasons, the trial court concluded that SynEcology “purposefully and knowingly, and 

in bad faith, failed to provide accurate responses to the document requests for the emails from 

the Comcast account.” As a result, SynEcology’s complaint was dismissed. This appeal 

followed. 

¶ 17. On appeal, SynEcology contends that the trial court erred in dismissing its claims 

for four reasons: (1) the circumstances called for a less drastic sanction than dismissal; (2) the 

dismissal was not related to a claim at issue in the discovery order; (3) the dismissal was based 

on objectively erroneous premises; and (4) the dismissal was without prior warning. 

¶ 18. Under Vermont Rule of Civil Procedure 37, the trial court has discretion to

sanction a party in varying degrees of severity for “fail[ure] to obey an order to provide or permit 
7

discovery.” V.R.C.P. 37(b)(2). If warranted by a finding of gross indifference, bad faith, or 

willfulness, coupled with substantial prejudice to the moving party, the trial court may dismiss

the action or proceeding. John v. Med. Ctr. Hosp. of Vt., Inc., 136 Vt. 517, 519, 394 A.2d 1134, 

1135 (1978). Imposition of sanctions under this rule “is necessarily a matter of judicial 

discretion” that is “not subject to appellate review unless it is clearly shown that such discretion 

has been abused or withheld.” Id. at 519, 394 A.2d at 1135; accord State v. Lee, 2007 VT 7, 

¶ 15, 181 Vt. 605, 924 A.2d 81 (mem.) (“As with other discovery rulings, the decision to impose 

sanctions for failure to comply with an order compelling discovery lies well within the trial 

court’s discretion.” (quotation omitted)).

¶ 19. Notwithstanding this broad discretion, we have held that “where the ultimate 

sanction of dismissal is invoked it is necessary that the trial court indicate by findings of fact that 

there has been bad faith or deliberate and willful disregard for the court’s orders, and further, that 

the party seeking the sanction has been prejudiced thereby.” Med. Ctr. Hosp. of Vt., Inc., 136 

Vt. at 519, 394 A.2d at 1135. “The imposition of the dismissal sanction cannot be imposed 

merely as punishment for failure to comply with the court’s order.” Id. Rather, the party’s 

failure must evidence “flagrant bad faith” and “callous disregard of responsibilities counsel owe 

to the court and to their opponents.” Id. at 520, 394 A.2d at 1135 (citing Nat’l Hockey League v. 

Metropolitan Hockey Club, Inc., 427 U.S. 639, 642 (1976)); accord Rathe Salvage, Inc. v. R. 

Brown & Sons, Inc., 2008 VT 99, ¶ 12, 184 Vt. 355, 965 A.2d 460 (“Despite trial courts’

otherwise broad discretion to impose discovery sanctions . . . litigation-ending sanctions are 

reserved for only the most flagrant cases and are inappropriate where failure to produce 

discovery is due to an inability fostered by circumstances outside of the party’s control.”). 

Failure to comply with the trial court’s discovery orders may be deemed willful when
8

the court’s orders have been clear, when the party has understood 

them, and when the party’s non-compliance is not due to factors 

beyond the party’s control. In addition, a party’s persistent refusal 

to comply with a discovery order presents sufficient evidence of 

willfulness, bad faith or fault.

Handwerker v. AT&T Corp., 211 F.R.D. 203, 209 (S.D.N.Y. 2002) (citations and internal 

quotations marks omitted), aff’d, 93 F.App’x 328 (2d Cir. 2004) (mem.).

¶ 20. Further, a party is prejudiced if the failure impairs their “ability to go to trial or 

threaten[s] to interfere with the rightful decision of the case.” Adriana Intern. Corp. v. Thoeren, 

913 F.2d 1406, 1412 (9th Cir. 1990) (citation omitted). The “[f]ailure to produce documents as 

ordered . . . is considered sufficient prejudice.” Id. Although the law presumes prejudice from 

unreasonable delay, the presumption may be rebutted, and unless frivolous, will shift the burden 

to the moving party to show at least some actual prejudice. In re Eisen, 31 F.3d 1447, 1452-53

(9th Cir. 1994) (citation omitted). It is then for the nonmoving party to persuade the trial court 

that “the claims of prejudice are either illusory or relatively insignificant when compared to the 

force of his excuse.” Id. at 1453 (quotation omitted). 

¶ 21. SynEcology’s contention that the circumstances called for a less drastic sanction 

than dismissal is incorrect because the trial court’s order includes findings that describe a pattern 

of conduct that satisfies the standard articulated in Med. Ctr. Hosp. of Vt., Inc., and therefore 

warrants dismissal. The trial court reviewed the thirty-four month long discovery process, which 

included multiple requests for supplemental production by Business RunTime and two motions 

to compel. In drawing the conclusion that SynEcology acted in bad faith, the trial court 

specifically noted SynEcology’s repeated insistence that it had produced all emails from the

Comcast account, which it later retracted, without explanation, when that insistence was shown 
9

to be false.

3 With regard to its finding that SynEcology acted with deliberate and willful 

disregard for the court’s orders, the trial court noted SynEcology’s failure to produce a privilege 

log, despite promising to do so on at least three occasions and being compelled to do so by a 

court order. Further, the trial court found Business RunTime was prejudiced by this behavior 

because: (1) the case was delayed for more than two years; (2) it was required to engage in 

unneeded motion practice to obtain materials it was properly entitled to; and (3) it suffered 

increased attorneys’ fees. Considering this, combined with SynEcology’s repeated failures to 

comply with the production requests, including its failure to produce a privilege log, its 

numerous unmet promises to do so, and the production of additional emails without explanation,

the trial court properly concluded that SynEcology “purposefully and knowingly, and in bad 

faith, failed to provide accurate responses to the document requests for the emails from the 

Comcast account” or an explanation for failing to comply with the trial court’s May 2014 order 

to produce a privilege log. 

¶ 22. SynEcology contends that the trial court’s dismissal was in error because it was 

not related to a particular claim at issue in the discovery order. SynEcology argues that it was 

incumbent on the trial court to explain how the alleged discovery failures were serious enough to 

justify dismissal. Discussing Rule 37(b)(2)(A) of the Federal Rules of Civil Procedure, which 

mirrors Rule 37(b)(2)(A) of the Vermont Rules of Civil Procedure, the U.S. Supreme Court in 

Insurance Corp. of Ireland Ltd. v. Compagnie des Bauxites de Guinee, 456 U.S. 694, 705-06

(1982), held that it does not violate due process to render a default judgment against a defendant 

who fails to comply with a pretrial discovery order. The Court found that “the preservation of 

due process was secured by the presumption that the refusal to produce evidence material to the 

 

3

 SynEcology’s retraction was prompted by Business RunTime obtaining copies of some 

of the emails from Mr. Kenney’s Comcast account. The record does not reflect whether 

SynEcology ever produced any such emails.
10

administration of due process was but an admission of the want of merit in the asserted defense.” 

Id. at 705 (quoting Hammond Packing Co. v. Arkansas, 212 U.S. 322, 350-51 (1909)). “Due 

process is violated only if the behavior of the defendant will not support the Hammond Packing

presumption,” and “[a] proper application of Rule 37(b)(2) will, as a matter of law, support such 

a presumption.” Id. at 706. 

¶ 23. Here, SynEcology’s discovery abuses go to the heart of the case: it was asked to 

produce all emails relevant to the merits of its claims, and it willfully failed to do so, and indeed, 

misrepresented their existence to the trial court. These repeated failures to produce evidence 

central to proving or disproving its claims easily meet the Hammond Packing presumption, and 

the trial court’s dismissal does not, therefore, offend due process. 

¶ 24. SynEcology’s argument that the trial court’s dismissal was based on objectively 

erroneous premises is also incorrect. In its brief, SynEcology contends that its supplemental 

production on December 30, 2014 remedied prior insufficiencies. Specifically, SynEcology 

alleges that the thirty-eight emails referenced as missing in the contempt ruling were, to its “best 

knowledge,” included in the documents produced on December 30, 2014. The Court finds no 

support in the record for these assertions. As stated above, the record does not reflect the 

number of emails produced on December 30, 2014, nor does it indicate the date, sender, 

recipient, contents, or subject lines of the emails included on the CD provided by SynEcology on 

that date. Furthermore, although SynEcology indicated that “[i]tems that are not being produced 

based on a claim of privilege shall be identified by way of a privilege log which shall be 

provided under separate cover,” there is nothing in the record indicating that SynEcology 

produced a privilege log at any time following the December 30, 2014 discovery certificate. The 

trial court noted that because of SynEcology’s flagrant disregard of discovery requests and its 

admission that it lied about the Comcast emails, it had become impossible to know whether there 
11

were additional relevant documents improperly withheld. Therefore, the assertion that the court 

was acting under objectively erroneous premises in dismissing the action is not supported by the 

record. The discovery certificate did not inform the court of what had been produced and, like 

earlier discovery representations by Synecology, was facially incomplete in the absence of 

record evidence supporting the production of a privilege log concerning emails that were 

admittedly not produced.

¶ 25. For these reasons, the trial court’s decision satisfies the requirement for dismissal, 

outlined in Med. Ctr. Hosp. of Vt., Inc. The trial court has broad discretion in imposing 

sanctions, and we will not disturb its findings absent a showing that discretion was abused or 

entirely withheld. Id. 136 Vt. at 519, 394 A.2d at 1135. Although dismissal is a severe sanction, 

on these facts we find that the trial court’s exercise of discretion can be easily sustained.

¶ 26. We disagree with SynEcology’s claim that the dismissal of the action without a 

hearing on the motion for contempt was error. In its brief, SynEcology suggests that the hearing 

on September 29, 2014 was devoted entirely to attorney O’Neill’s motion for leave to withdraw, 

rather than the motion for sanctions, and that the trial court indicated that it would hold a second 

hearing on the motion. At the hearing on September 29, following a discussion regarding the 

motion for leave to withdraw, Business RunTime stated, “we do have a motion for contempt that 

is fully briefed.” Following a discussion about whether to rule on that motion at the hearing, the 

trial court stated:

[I] want to be fair to [SynEcology]. . . . I could do what [Business 

RunTime] is asking and just say I’m going to decide this motion 

now and whatever remedy I think is appropriate, I’ll do before you 

get a new lawyer, but I would rather have you consult somebody 

else first. So I am going to give you time to get another lawyer and 

let the other lawyer file something else before I rule on the motion.
12

The trial court then informed SynEcology that it would receive a standard form in the mail with 

the deadline to obtain counsel and file a notice of appearance. Following a discussion between 

the trial court and Mr. Kenney about this deadline, the trial court stated, “we definitely do need 

one thing from you though, Mr. Kenney, which is the mailing address that should be used for the 

hearing—the form that I just said we are going to send.” 

¶ 27. SynEcology now argues that the trial court intended that a hearing on the motion 

for contempt would precede any ruling. It bases this argument on the trial court’s final remarks, 

when it stated, “the hearing—the form I just said we are going to send.” When read in context, 

however, it is clear from the trial court’s remarks that they were made in reference to the form 

indicating the deadline for filing anything in response to the motion for contempt, and not in 

reference to a hearing on that motion. As reflected by the record, neither party requested a 

hearing with respect to the motion for contempt pursuant to Rule 78(b)(2). See V.R.C.P. 

78(b)(2) (“An opportunity to present evidence shall be provided, if requested. . . . In any case, 

the court may decline to hear oral argument and may dispose of the motion without argument.”); 

Shaw v. Barnes, 166 Vt. 610, 610, 693 A.2d 710, 711 (1997) (mem.) (holding that civil rules 

give trial court discretion to decline oral argument on motions in all cases).

¶ 28. Despite the fact that neither party requested one, the trial court initially scheduled 

a hearing on the contempt motion. The trial court used the majority of that hearing to discuss the 

subsequently-filed motion to withdraw by Synecology’s counsel, although the pending contempt 

motion seeking dismissal was also discussed. At the hearing, the trial court informed 

Synecology that before ruling upon the contempt motion, it would allow time for substitute 

counsel and supplemental pleading. This is exactly what the trial court did. Synecology’s new 

counsel filed the supplemental pleading, but did not request a hearing on the motion. Rule

78(b)(2) authorizes a court to dispose of a motion without argument, and the decision to do so is 
13

within the discretion of the court. Bandler v. Cohen Rosenthal & Kramer, LLP, 2015 VT 115, 

¶ 11, ___ Vt. ___, ___ A.3d ___ (“The Vermont Rules of Civil Procedure give the trial court 

discretion in deciding whether to hear argument.”). Error in the decision not to hold a hearing 

requires an affirmative showing the court abused or withheld its discretion. Id. ¶ 10. Based on 

the record, especially where neither party requested a hearing, that showing has not been made. 

¶ 29. We leave for another day whether, under certain circumstances, a warning prior to 

dismissal may be required. Where, as here, the motion itself specifically seeks dismissal as a 

sanction, no purpose is served by any additional warning from a court that it is considering 

dismissal. Here, the trial court’s order dismissing the complaint was in response to Business 

RunTime’s motion for contempt, sanctions, and attorneys’ fees. The first sentence of that 

motion put SynEcology on notice that the sanction of dismissal was being requested. That 

sentence provides:

 Defendant Business RunTime, Inc. . . . hereby move[s] this Court 

pursuant to V.R.C.P. 37(b) to hold Plaintiff SynEcology Partners 

L3C in contempt for failure to comply with this Court’s May 22, 

2014 compulsion order, and further move this Court to dismiss this 

case and for attorney’s fees. (emphasis added).

It was clear from the motion that the court must, necessarily, consider whether to grant the 

requested relief. Further, SynEcology was given additional notice at the hearing on September 

29, 2014, when Business RunTime’s counsel reiterated that dismissal was being sought as a 

sanction. That SynEcology may not have felt dismissal was a likely outcome is far different than 

not knowing the issue was before the court.

¶ 30. Synecology’s conduct regarding discovery, which the trial court’s order describes,

was sufficient to justify the animadversion of the court. It is clear from its discussion that the 

trial court lost faith in SynEcology’s willingness to undertake a good faith effort to comply with 

the discovery orders or motions to compel. Although SynEcology argues that it was willing and 
14

able to produce the Comcast emails and privilege log, the trial court had no reason to believe 

SynEcology would suddenly make good on its promises having failed to do so in the past. 

Affirmed.

FOR THE COURT:

Associate Justice