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
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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., Cal. Bus. & Prof. Code §§ 16600(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 id. § 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 
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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 Massachusettsheadquartered 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 
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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 28 

U.S.C. § 1292(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, 40 F.4th 

1, 9 (1st Cir. 2022); NuVasive, Inc. v. Day, 954 F.3d 439, 443 

(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, 954 F.3d at 443. On abuseof-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, 40 F.4th 

at 25. But on de novo review, we give no deference to what the 

judge thought, see Berge v. Sch. Comm. of Gloucester, 107 F.4th 

33, 39 n.8 (1st Cir. 2024) — not because we're better or smarter 
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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, 499 U.S. 225, 232, 233 (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., 360 F.3d 1, 4 (1st Cir. 2004). 

See also generally Smith v. Gen. Motors LLC, 988 F.3d 873, 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 reliedon 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, 533 F.3d 42, 45 (1st Cir. 

2008).
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Massachusetts usually respects the parties' choice of 

law. See NuVasive, 954 F.3d at 443; see also Oxford Glob. Res., 

LLC v. Hernandez, 106 N.E.3d 556, 564 (Mass. 2018); Feeney v. Dell 

Inc., 908 N.E.2d 753, 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, 106 

N.E.3d at 564. 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 id. at 563-64 (brackets and quotation marks omitted); see also

NuVasive, 954 F.3d at 444. 

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

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

anywhere. See NuVasive, 954 F.3d at 444; see also Feeney, 908 

N.E.2d at 766-67. But he can't satisfy the materially-greaterinterest 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, 821 

F. App'x 553, 555 (6th Cir. 2020) (stressing that that court only 
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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, 373 

F.3d 861, 868 (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., 

362 F.3d 786, 799 (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 106 N.E.3d at 561 n.3 — was "materially greater" 

than Massachusetts's interest in enforcing it, see id. at 564. 

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.
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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 Massachusettsbased former employer Oxford "in California," and had "allegedly 

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

and joined a California competitor, id. at 566 (emphasis added) —

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

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

confidentiality provisions," id. at 560, 569-70. Plus Oxford also 

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

employment with Oxford — [had been] located exclusively in 

California." Id. at 563 (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 21⁄2-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 
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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 Oxfordbased 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 106 N.E.3d at 

564-65 (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 

2 For similar reasons, Hermalyn gets no help from DCS 

Sanitation Mgmt., Inc. v. Castillo, 435 F.3d 892 (8th Cir. 2006), 

Cardoni v. Prosperity Bank, 805 F.3d 573 (5th Cir. 2015), and 

Waithaka v. Amazon.com, Inc., 966 F.3d 10 (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 435 F.3d at 896-

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 805 F.3d at 576-78, 584. 

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 966 F.3d at 

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

night and day.
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"stronger substantive and procedural protections than in the past" 

and also "limit[ing]" employers "to substantially reduced postemployment restrictions." See Jerry Cohen et al., Employee 

Noncompetition Laws and Practices: A Massachusetts Paradigm Shift 

Goes National, 103 Mass. L. Rev. 31, 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 id. 

Interestingly — and we think tellingly — a Massachusetts legislator 

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

"in 2009," see id. at 53 (emphasis added), a bill "modeled" after 

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

and Compromise (Aug. 13, 2018), https://willbrownsberger.com/astudy-in-persistence-and-compromise-legislation-regulatingagreements-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 id. And they "promised to leave the 

state if [his] legislation passed." See id. That bill ultimately 

went nowhere, however. See id. But after years and years of 

legislative give-and-take, "a hard fought compromise" emerged that 
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"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 id. (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 106 N.E.3d 

3 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."
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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 postemployment restrictions." See id. (emphases added). Which 

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

5 Roll Sys., Inc. v. Shupe, No. CIV.A.97-12689, 1998 WL 

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," 
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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 pushand-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 "choiceof-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 
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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. 

7 Application Grp., Inc. v. Hunter Grp., Inc., 72 Cal. Rptr. 

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 id. at 76, 

86. 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 id. at 86, 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. 

8 Hermalyn writes that "[s]eparate and apart from the grounds 

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, 2024 WL 3879954, at *14 (N.D. Tex. Aug. 20, 2024) 

(concluding that because the commission lacked the power to issue 
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Irizarry, 587 F.3d 464, 487 (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., id.

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., 716 F.2d 1023, 1035 (4th Cir. 1983), Keener

v. Convergys Corp., 342 F.3d 1264, 1268-69 (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.
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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, 314 Cal. Rptr. 

3d 890, 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. 
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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.