United States Court of Appeals For the First Circuit

No. 24-1443

DRAFTKINGS INC.,

Plaintiff, Appellee,

v.

MICHAEL HERMALYN,

Defendant, Appellant.

APPEAL FROM THE UNITED STATES DISTRICT COURT FOR THE DISTRICT OF MASSACHUSETTS

[Hon. Julia E. Kobick, U.S. District Judge]

Before

Kayatta, Thompson, and Montecalvo, Circuit Judges.

Christopher G. Michel, with whom Gregg M. Badichek, Aliki Sofis, Alexander S. del Nido, Issac Saidel-Goley, Quinn Emanuel Urquhart & Sullivan, LLP, Russell Beck, Stephen D. Riden, and Beck Reed Riden LLP were on brief, for appellant. Thomas H. Dupree Jr., with whom Jacob T. Spencer, Orin S. Snyder, Harris M. Mufson, Justine M. Goeke, Gibson, Dunn & Crutcher LLP, Mark C. Fleming, William F. Lee, Andrew S. Dulberg, and Wilmer Cutler Pickering Hale and Dorr LLP were on brief, for appellee. September 26, 2024 THOMPSON, Circuit Judge.

STAGE-SETTING

Massachusetts and California aren't exactly on the same

page when it comes to noncompete agreements.

Massachusetts generally allows noncompetes if they

comply with certain restrictions (for example, employers can't

require all employees to sign them (excluded employees include

persons aged 18 or younger) and the noncompete period can't last

more than a year (except if the employee breached a fiduciary duty

to the employer or stole the employer's property, in which case a

2-year cap applies)). See, e.g., Mass. Gen. Laws ch. 149,

§ 24L(b)(iv), (c). California generally bans noncompetes unless

they squeeze within one of the few narrow exceptions (like for

noncompetes in a business sale or a partnership breakup). See,

e.g.,

(a), 16601, 16602. And that's

true "regardless of where and when the contract was signed" and

"whether . . . the employment was maintained outside of

California." See

§ 16600.5(a), (b).

Today's case plays out against the backdrop of these

different policy choices. We streamline the facts and procedural

history (rather aggressively) to lay bare the nature of the

disputes before us, adding more details later as needed for

specific issues (an example of streamlining is our ignoring a

- 3 - California state-court lawsuit involving some of the same parties

as here, because that suit doesn't affect our analysis).

As recently as the beginning of this year, then-New

Jersey resident Michael Hermalyn had a plum job with Massachusetts-

headquartered DraftKings. But he quit to take a similar job with

rival Fanatics's California-based subsidiary, a position (he says)

that requires him to live and work in Los Angeles. DraftKings and

Fanatics (for anyone who hasn't seen their ads) are sports betting

and online gaming companies (a description that simplifies things

a bit but is enough for now).

DraftKings thought (among other concerns) that

Hermalyn's new post violated a noncompete he had signed before

quitting — an agreement that had a Massachusetts choice-of-law

proviso and a one-year noncompete clause. So DraftKings sued him

in Massachusetts federal court for breach of the noncompete (along

with other claims not relevant here).

Everyone seems to agree (at least for present purposes)

that if the noncompete is enforceable, Hermalyn breached it by

joining Fanatics. Not surprisingly then, DraftKings asked the

district judge to use Massachusetts law and Hermalyn asked her to

use California law. Siding with DraftKings, the judge — after

using Massachusetts law — ruled the noncompete enforceable and

preliminarily enjoined Hermalyn from competing against DraftKings

- 4 - in the United States for one year (she did reject DraftKings's

request for a worldwide injunction, however).

Hermalyn then filed this interlocutory appeal, see

(a)(1), making two alternative arguments. The first

is that the judge wrongly held that Massachusetts law governed the

enforceability of the noncompete. The second is that if

Massachusetts law does govern, then the judge should've excluded

California from the preliminary injunction's scope.

Having considered the matter on an expedited basis, we

let the challenged order stand. Read on to learn why.

CHOICE OF LAW

Standards of Review

We examine the judge's preliminary-injunction grant for

abuse of discretion. See We the People PAC v. Bellows,

(1st Cir. 2022); NuVasive, Inc. v. Day,

(1st Cir. 2020). Within that system, however, we inspect legal

questions (like which state's law applies) de novo and findings of

fact for clear error. See NuVasive,

. On abuse-

of-discretion review, we defer to the judge if she didn't make an

obvious mistake of judgment (a material legal misstep is a per se

abuse of discretion, for example). See We the People PAC,

. But on de novo review, we give no deference to what the

judge thought, see Berge v. Sch. Comm. of Gloucester,

, 39 n.8 (1st Cir. 2024) — not because we're better or smarter

- 5 - than our district-court colleagues (we aren't!) but because of the

"institutional advantages" we have over them (including sitting on

multi-member panels, a process that "permit[s] reflective dialogue

and collective judgment" and so "promotes decisional accuracy"),

see Salve Regina Coll. v. Russell,

(1991).1

Massachusetts Law

Because — as the parties agree — diversity jurisdiction

exists over the breach-of-noncompete claim, the "forum" of

Massachusetts (where DraftKings sued Hermalyn) sets the rules for

which state's law decides the noncompete's enforceability (even

though the noncompete itself picked Massachusetts). See Reicher

v. Berkshire Life Ins. Co. of Am.,

(1st Cir. 2004).

See also generally Smith v. Gen. Motors LLC,

, 879 n.

5 (6th Cir. 2021) (explaining that "even contracts that contain

choice-of-law clauses are themselves analyzed under some state's

law should a controversy arise over the validity of that clause

itself"). So on to Bay State law then.

1 Hermalyn seemingly implies that our review of facts underlying a choice-of-law ruling isn't for clear error (to the extent anyone challenges the findings, of course), but remains de novo. He cites no on-point case that says so, however (his relied- on decisions say that we review a choice-of-law ruling de novo, but don't say that the facts behind the ruling get something other than clear-error treatment). And that's probably because the Federal Reporter is filled with opinions explaining our "usual" tradition of inspecting fact-findings for "clear error." See, e.g., Fayard v. Ne. Vehicle Servs., LLC,

, 45 (1st Cir. 2008).

- 6 - Massachusetts usually respects the parties' choice of

law. See NuVasive,

; see also Oxford Glob. Res.,

LLC v. Hernandez,

(Mass. 2018); Feeney v. Dell

Inc.,

, 766 (Mass. 2009). But exceptions exist,

each driven by public-policy concerns (the term "usually" in the

last sentence was a tipoff about exceptions). See Oxford,

. And the exception Hermalyn invokes requires him to

show that (i) "application of" Massachusetts law "would be

contrary to a fundamental policy of" California; (ii) California

"has a materially greater interest than" Massachusetts "in the

determination of the . . . issue"; and (iii) California is the

state whose law would control "in the absence of an effective

choice of law by the parties" — i.e., that California has "the

most significant relationship to the transaction and the parties."

See

(brackets and quotation marks omitted); see also

NuVasive,

.

The word linking the above-listed requisites is "and,"

not "or." Which means Hermalyn must satisfy all of them to get

anywhere. See NuVasive,

; see also Feeney, 908

N.E.2d at 766-67. But he can't satisfy the materially-greater-

interest requisite (as we explain next), thus dashing his hopes of

winning the issue (even assuming without deciding that he could

satisfy the others). See Down-Lite Int'l, Inc. v. Altbaier,

, 555 (6th Cir. 2020) (stressing that that court only

- 7 - had to "examine the materially-greater-interest prong to show why

[it] will not upset the parties' choice-of-law provision"). See

also generally Commodity Futures Trading Comm'n v. Zelener,

(7th Cir. 2004) (Easterbrook, J., for the court)

(stating that sometimes it's "[b]est to take Occam's Razor and

slice off needless complexity"); PDK Lab'ys. Inc. v. U.S.D.E.A.,

(D.C. Cir. 2004) (Roberts, J., concurring in

part and concurring in the judgment) (noting that "if it is not

necessary to decide more, it is necessary not to decide more").

Arguments and Analysis

The centerpiece of Hermalyn's argument is that Oxford —

an opinion by the Massachusetts Supreme Judicial Court ("SJC") —

makes the materially-greater-interest issue open-and-shut in his

favor. That's because, he continues, Oxford held that a

Massachusetts choice-of-law clause there couldn't "survive" since

California's interest in not enforcing the contract — a

"Confidentiality, Non-Solicitation and Non-Competition

Agreement," see

n.3 — was "materially greater"

than Massachusetts's interest in enforcing it, see

.

And applying Oxford evenhandedly, he submits, entitles him to a

victory here.

Unfortunately for Hermalyn, Oxford can't do the work

that he asks of it.

- 8 - In pressing his Oxford-centric arguments, Hermalyn

mentions how "California" is "where [he] currently resides, works,

and allegedly breached the non-compete covenant." But Oxford held

that "California ha[d] a materially greater interest than

Massachusetts" there "because" the employee Hernandez had

"executed" and "performed" the contract with his Massachusetts-

based former employer Oxford "in California," and had "allegedly

committed a breach of the agreement in California" after he quit

and joined a California competitor,

(emphasis added) —

Hernandez (you see) lived and worked in California before and after

he "allegedly violated" the agreement's "nonsolicitation and

confidentiality provisions,"

. Plus Oxford also

noted that the "subject matter of the contract — Hernandez's

employment with Oxford — [had been] located exclusively in

California."

(emphases added). Hermalyn's facts are

not like Hernandez's. According to what the judge here found —

and we see no convincingly developed argument contesting her

findings as reversible error — (i) while "Hermalyn primarily worked

for [Massachusetts-headquartered] DraftKings from New Jersey and

New York, he traveled to Massachusetts for work at least 25 times"

during a 2½-year stretch before leaving for Fanatics — which

roughly comes to "once every [6] weeks"; (ii) "Hermalyn does not

contend, nor is there evidence, that he performed any of his work

responsibilities for DraftKings from California"; and (iii) "[a]ny

- 9 - harms flowing from Hermalyn's likely" noncompete breach "will be

felt by DraftKings in Massachusetts, not California." Given the

dissimilarities between Oxford and our case, Hermalyn's Oxford-

based arguments sputter out.2

Hermalyn is right about one thing, however. Oxford did

say that California's "legislative[ly]" declared "policy" interest

"in favor of open competition and employee mobility" was

"materially greater" than Massachusetts's — a state, Oxford added,

that lacked a "statute akin" to California's. See

(quotation marks omitted). But "a paradigm shift" occurred

when Massachusetts passed a law — the Massachusetts Noncompetition

Agreement Act ("MNAA") — that "dramatically reduc[ed] the number

of Massachusetts employees who can be subjected to . . .

enforceable" noncompetes, while giving those exposed to them

2For similar reasons, Hermalyn gets no help from DCS Sanitation Mgmt., Inc. v. Castillo,

(8th Cir. 2006), Cardoni v. Prosperity Bank,

(5th Cir. 2015), and Waithaka v. Amazon.com, Inc.,

(1st Cir. 2020). DCS held that Nebraska had a materially greater interest than Ohio (the contractual choice-of-law state) in the matter because (among other things) the employees lived and worked in Nebraska before and after the alleged noncompete breaches. See

- 97. Cardoni ruled that Oklahoma had a materially greater interest than Texas (the contractual choice-of-law state) in the matter because (among other things) the employees worked in Oklahoma before and after the alleged breach. See

. And Waithaka noted that Massachusetts had a materially greater interest than Washington (the contractual choice-of-law state) in the matter because the worker "indisputably performed all of his work pursuant to the contract" in Massachusetts. See

. Compare those cases with Hermalyn's and the differences are night and day.

- 10 - "stronger substantive and procedural protections than in the past"

and also "limit[ing]" employers "to substantially reduced post-

employment restrictions." See Jerry Cohen et al., Employee

Noncompetition Laws and Practices: A Massachusetts Paradigm Shift

Goes National,

, 31 (2022).

The MNAA was no off-the-cuff, spur-of-the-moment bit of

legislating either. Far from it. The law "gestat[ed]" during a

decade's worth of legislative study and debate. See

Interestingly — and we think tellingly — a Massachusetts legislator

actually "propose[d] a bill to completely ban" noncompetes back

"in 2009," see

(emphasis added), a bill "modeled" after

"California" law, see Will Brownsberger, A Study in Persistence

and Compromise (Aug. 13, 2018), https://willbrownsberger.com/a-

study-in-persistence-and-compromise-legislation-regulating-

agreements-not-to-compete/[https://perma.cc./DBV6-VXMH] (emphasis

added) (stating that "the venture capital community" thought that

"California's prohibition of [noncompetes] was a major reason for

California's dominance in technology entrepreneurship").

Concerned Bay State business leaders then stressed how "essential"

noncompetes are "for protecting the ideas that they had developed

through great effort." See

And they "promised to leave the

state if [his] legislation passed." See

That bill ultimately

went nowhere, however. See

But after years and years of

legislative give-and-take, "a hard fought compromise" emerged that

- 11 - "bann[ed]" noncompetes "for lower level workers, limit[ed] them

for higher level workers[,] and provid[ed] procedural protections

to assure that workers know what they are getting into when they

sign them." See

(emphasis added); see also Cohen et al.,

supra, at 32-33 (discussing the history of the bill's enactment).

The MNAA became law in August 2018, just days before the

SJC's September 2018 Oxford ruling. See 2018 Mass. Legis. Serv.

ch. 228, § 71. But the MNAA applies only to noncompetes "entered

into on or after October 1, 2018."3 See id. (emphasis added).

Which explains why Oxford never even hinted that the MNAA played

any role there. And which also shows that Oxford had in mind the

state of law before the MNAA when it talked about California's

interest being "materially greater" than Massachusetts's — not the

state of the law after the MNAA.

Perhaps anticipating some of these points, Hermalyn

notes that Oxford "predate[s]" California's 2024 passage of laws

reinforcing its deep-rooted policy against restraint of trade.4

But the fact still remains that Oxford — which (as we said)

acknowledged California's "settled legislative policy" of

promoting "open competition and employee mobility," see

Hermalyn's noncompete specifically cites to the MNAA. 4 The drafting committee for these statutes conceded that while they "express[ed] California's strong desire to enforce its public policy," they "cannot dictate to courts outside of its jurisdiction."

- 12 - at 564 (quotation marks omitted and emphasis added) — ran the

materially-greater-interest analysis without having to factor in

the MNAA (because (again) the MNAA wasn't in play there).

Still looking for a winning argument, Hermalyn writes

that "the MNAA did not purport to abrogate Massachusetts law as

discussed and understood in Oxford," quoting for support this

snippet from the Massachusetts Law Review article mentioned above:

the MNAA "codified aspects of the common law that will continue to

require case-by-case exposition." See Cohen et al., supra, at 31.

Hermalyn's point seems to be that the MNAA didn't change Bay State

"law or policy of limited tolerance towards non-compete

covenants." But the article's animating thesis — revealed in the

following excerpts (we quoted some of them a few paragraphs back)

— couldn't be any clearer: the MNAA "represents a paradigm shift

in favor of employees" that "dramatically reduc[ed] the number of

Massachusetts employees who can be subjected to . . . enforceable"

noncompetes, while offering those covered by them "stronger

substantive and procedural protections than in the past" and

likewise "limit[ing]" employers "to substantially reduced post-

employment restrictions." See id. (emphases added). Which

scotches Hermalyn's attempt to downplay the MNAA's significance.5

Roll Sys., Inc. v. Shupe, No. CIV.A.97-12689,

5

1785455 (D. Mass. Jan. 22, 1998) — cited by Hermalyn — doesn't compel a different result. Highlighting California's "fundamental policy against the enforcement of [broad] restrictive covenants,"

- 13 - Given this tableau — involving (among other features)

two states passing laws reflecting different but careful balances

of conflicting forces in the noncompete area (after the usual push-

and-pull of politics), with Massachusetts opting not to mimic

California's ban and instead generally allowing noncompetes for

higher-level employees like Hermalyn (who unlike lower-level

employees often have business-sensitive info and deep ties with

company customers) — we can't say that Hermalyn has shown (as he

was required to do) that California's "interest" in pursuing its

policy is not just "greater" than Massachusetts's, but is

"materially" so. See Down-Lite, 821 F. App'x at 556 (acknowledging

that "California has a meaningful interest in protecting its

resident from" his Ohio-based former employer's "desire to

restrict competitive conduct," but holding that "that interest is

not materially greater than Ohio's interest in protecting one of

its closely held businesses operating in the global economy").6

see id. at *2, Roll Sys. "disregard[ed]" a Massachusetts "choice- of-law provision in the contract and appl[ied] California law instead," in a case involving a preliminary-injunction dispute pitting an employee and his current employer against his former employer, see id. at *1-3. But Roll Sys. came many years before the MNAA. Which — whatever else may be said about Roll Sys. — is enough to distinguish that case from Hermalyn's. 6 DraftKings makes many of the same points about Massachusetts's public policy on noncompetes. Unimpressed with DraftKings's effort, Hermalyn blasts the company for "mak[ing] no headway in attempting to equate Massachusetts'[s] policy interests with California's." But his protest ignores that he (not DraftKings) had to show (as the above-text explains) not just that California's interest equals Massachusetts's, or even that it's

- 14 - Or to put it differently but with the same result, he hasn't shown

that "California's public policy" eclipses "the parties' clear and

unambiguous agreement to apply [Massachusetts] law." See id.7

Wrap-Up

The short of it is that the judge didn't err by ruling

that Massachusetts law governs Hermalyn's noncompete with

DraftKings.8

SCOPE OF THE PRELIMINARY INJUNCTION

Standard of Review

Judges must closely tailor injunctive relief to the

specific harm alleged. See, e.g., Vaquería Tres Monjitas, Inc. v.

greater than Massachusetts's, but that it's materially greater than Massachusetts's. Which (again) he hasn't done. Application Grp., Inc. v. Hunter Grp., Inc.,

2d 73 (Cal. Ct. App. 1998), isn't a difference-maker for Hermalyn either — despite what he thinks. Application did hold that California had a materially greater interest in noncompetes than Maryland (the contractual choice-of-law state). See

. But there — unlike here — "[t]here [was] no showing that [the employee] was attempting to exploit [the former employer's] trade secrets or other protected information," see

, a distinguishing point raised in DraftKings's answering brief without contradiction from Hermalyn in his reply brief. Also making this case worlds apart from Hermalyn's is that (as we just said) Application addressed whether California had a materially greater interest in noncompetes than Maryland, not Massachusetts. Hermalyn writes that "[s]eparate and apart from the grounds 8

outlined in []his brief, enforcement of" the noncompete "will also be precluded by the recently promulgated Federal Trade Commission . . . rule barring most" noncompetes. But he adds that he hasn't "sought relief based on th[at] rule" since it's not yet in "effect." See generally Ryan, LLC v. Fed. Trade Comm'n, No. 3:24- CV-00986-E,

, at *14 (N.D. Tex. Aug. 20, 2024) (concluding that because the commission lacked the power to issue

- 15 - Irizarry,

(1st Cir. 2009). And because they're

uniquely placed to design "the scope of injunctive relief to

[their] factual findings," we review only for abuse of discretion.

See, e.g.,

Arguments and Analysis

We can make quick work of Hermalyn's alternative

position: that if Massachusetts law controls DraftKings's bid to

enforce the noncompete, then the judge (under "comity and

federalism" principles) had to — but didn't — exclude California

from the preliminary injunction's scope given California's strong

"public policy barring the enforcement of such [agreements]

against California employees of California companies working in

California." We sidestep DraftKings's claim that Hermalyn waived

or forfeited this argument because as DraftKings also contends,

his argument fails regardless.

Starting with Hermalyn's public-policy point, we've

already explained above why California's policy can't override

Massachusetts's. And the cases he champions — Barnes Grp., Inc.

v. C & C Prods., Inc.,

(4th Cir. 1983), Keener

v. Convergys Corp.,

(11th Cir. 2003), and

Herman Miller, Inc. v. Palazzetti Imps. & Exps., Inc., 270 F.3d

that rule, "the [r]ule shall not be enforced or otherwise take effect" anywhere nationwide "on its effective date of September 4, 2024"). So we needn't say anything more on that subject.

- 16 - 298, 327 (6th Cir. 2001), where reviewing courts narrowed an

injunction's reach — don't move the needle either. Our reasons

for thinking so are simple. (i) California outlaws online sports

betting. See Tak Chun Gaming Promotion Co. v. Long,

, 897 (Cal. Ct. App. 2023). (ii) But a big part of Hermalyn's

job is creating and keeping relationships with digital-gaming

customers. (iii) So if he can join Fanatics in Los Angeles

straightaway, he'll inevitably interact with clients outside

California where online sports betting is legal. (iv) Clearly his

requested California carveout will give him a way to skirt the

countrywide preliminary injunction's one-year noncompete ban.

(v) And returning to his trio of cases with all this in mind, we

note that none covers a situation like ours — where lopping a state

off a USAwide preliminary injunction on a one-year noncompete would

entirely undercut that injunction's effectiveness. (vi) Which

goes to show that those cases hold no sway here. DraftKings made

each of these romanette-numbered points about the injunction's

breadth in its answering brief, with no pertinently persuasive

push back from Hermalyn in his reply brief.

- 17 - Wrap-Up

The bottom line is that the judge didn't err by including

California within the preliminary injunction's range.

LAST WORDS

All that's left to say is: affirmed, with appellate

costs to DraftKings.

- 18 -