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I'm visiting the States on ESTA, after which I'm flying on to Mexico, then to Cuba, then to Jamaica and then back to the States, then back home (Europe). From the first US entry to the final day in the US, not more than 90 days pass.

My ESTA expires five days after initial entry. From the CBP website: "If your ESTA expired after you arrived into the U.S., it will not affect your departure. However, once you have departed you will need to renew your ESTA in order to re-enter the U.S."

Mexico, Cuba and Jamaica are all listed as 'adjacent countries' that do not interrupt the 90-day-period when returning to the States, but I'm unsure about daisychaining more than one of them.

Does my flight from Jamaica to the US count as a re-entry by ESTA definitions?

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Your admission to the US, and your readmission for the remainder of your initial 90-day period of admission, are governed by the terms of the visa waiver program (VWP). ESTA is nothing more than authorization to travel to the US to apply for admission under the VWP. The provision for readmission is established in the Code of Federal Regulations at 8 CFR 217.3(b).

The actual waiver of the visa requirement and authorization to enter and remain in the US are effected by the immigration officer. That is, in fact, why it doesn't matter whether the ESTA expires while you're in the US.

Even if you will be readmitted for the remainder of your previous 90-day period of admission, you need valid ESTA authorization. Without it, you will be unable to board your flight. The requirement for ESTA is established at 8 USC 1187(a)(11):

(11) Eligibility determination under the electronic system for travel authorization

[...E]ach alien traveling under the program shall, before applying for admission to the United States, electronically provide to the system biographical information and such other information as the Secretary of Homeland Security shall determine necessary to determine the eligibility of, and whether there exists a law enforcement or security risk in permitting, the alien to travel to the United States. Upon review of such biographical information, the Secretary of Homeland Security shall determine whether the alien is eligible to travel to the United States under the program.

It is further elaborated at 8 CFR 217.5, which says at paragraph (b) that

Each alien falling within the provisions of paragraph (a) of this section must receive a travel authorization prior to embarking on a carrier for travel to the United States.

Paragraph (a), in turn, says

Each nonimmigrant alien intending to travel by air or sea to the United States under the Visa Waiver Program (VWP) must, within the time specified in paragraph (b) of this section, receive a travel authorization, which is a positive determination of eligibility to travel to the United States under the VWP via the Electronic System for Travel Authorization (ESTA), from CBP. In order to receive a travel authorization, each nonimmigrant alien intending to travel to the United States by air or sea under the VWP must provide the data elements set forth in paragraph (c) of this section to CBP, in English, in the manner specified herein, and must pay a fee as described in paragraph (h) of this section.

There's nothing here that changes the requirements for those "intending to travel by air or sea" to apply for readmission under a previous period of admission.

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This is one of those things where you might not have a problem doing nothing but it would only take one picky Immigration Officer to not only ruin your day, but your prospect of future travel to the USA to make it not worth it.

Furthermore, you might not be able to get onto the Jamaica to USA flight if the airline company also sees that you have an expired ESTA.

An ESTA is what, $14? To me, it’d be worth the peace of mind.

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    Think you're right, the ESTA just allows you to fly to the USA, but OP won't have an ESTA so they probably wouldn't let them board the plane
    – BritishSam
    Commented Sep 6, 2018 at 14:43
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    The problem won't be the immigration officer, but the airline. And even then, the problem won't be the airline, but the US APIS system. Will it indicate to the airline that the passenger is cleared to board? Almost certainly not.
    – phoog
    Commented Sep 6, 2018 at 15:50

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