The Headless Horseman – An ADA Halloween Tale

By Marti Cardi, VP-Product Compliance Gail Cohen, Director-Employment Law/Compliance

Business was great and Ichabod decided to expand his company, Crane’s Daylight Deliveries, to include Midnight Messengers.  Tired of whiling away his nighttime hours as a ghoul, Harry the Headless Horseman applied for a night messenger position with Crane’s – dropping off his résumé at midnight, of course.  In a hurry to get the new service off the ground, Ichabod hired Harry sight unseen on the strength of his résumé, which touted Harry’s many years of experience as a nighttime horseman familiar with the trails and roads around Sleepy Hollow.   He sent Harry a letter by his Daylight Deliveries service and asked him to start work that night.

Headless Harry’s gig called for him to pick up packages and letters for delivery, after dark, from the hollowed out oak tree next to Crane’s offices.  Nervous about those nighttime phantoms, Ichabod left work before dark and did not meet Harry right away.

Harry started work and loved the job – riding the familiar lanes, but with purpose; speeding important packages and messages to the local citizenry as soon as possible.  No more “delivered next day” if a package wasn’t dropped off at Crane’s before 3 pm!  Crane’s received accolades for being on the cutting edge of package delivery, and praise for the horseman who silently left packages by the doorstep and rode away into the night without so much as a “how do you do.”

Unfortunately – due to having to hold his head with one hand as he rode – Harry only had one hand to hold onto the parcels.  Although he delivered his bailments safely, it took him more trips to accomplish his nightly mission than if he could carry several items at once.  He sometimes failed to complete his essential task of making all deliveries before sunrise.  After a few days of work, and following Crane’s personnel policies, Harry asked for an accommodation to assist him in performing the essential functions of his job: saddlebags to tie onto his horse to put the packages in.  He would then be able to finish his work in the dark, as promised by Crane’s Midnight Messengers – boxes with breakfast!  It was more than a catchy tagline; it was a requirement of the position!

Ichabod received Harry’s request with alarm.  How much would these saddlebags cost?  None of his other couriers had these bags.  What was Harry’s problem, and would saddlebags really enable Harry to do the job?  Ichabod arranged to meet Harry at dusk on Hollow Bridge – very close to Ichabod’s abode so he could get home before dark – to discuss his request.

Imagine Ichabod’s panic when Harry showed up with his head resting on his saddle, held in place with one hand!  Why, no one could deliver packages without his head attached!  How could he read the addresses on the packages and find the destinations?  How could he ask directions if needed?  Ichabod almost fell out of his saddle when Harry greeted him loudly by name and held his head up (in his hands) to look Ichabod in the eye (as his mother had taught him to do when speaking with someone).

As you might have guessed, the rest of the story reads like an ADA nightmare.  Ichabod stuttered and spluttered but told Harry he could not grant the accommodation – the cost was too high, other messengers would want the same, and he could not treat Harry differently by giving him saddlebags.  And besides, Ichabod said, a horseman without a head simply could not do the job.  “You’re fired!”

Not surprisingly, Harry filed an EEOC charge against Crane’s Midnight Messengers, alleging discrimination based on disability and failure to accommodate.  Ichabod initially refused to settle Harry’s charge but, after the EEOC’s investigation, entered into a consent decree in Night Court.  Amid much publicity and expense, which Ichabod could have avoided if he had followed the  Boos! for Employers below, Ichabod and Crane’s Midnight Messengers paid Harry a 2-year supply of corn and pumpkins, plus another few bushels of each for Harry’s attorneys.

Pings (we mean Boos!) for employers:

Where did Ichabod and Crane’s go wrong?  Let’s count the ways:

  • Wisely, Ichabod did not contest that Harry had a disability: that was pretty open and obvious to all.
    But, he did not engage in the interactive process with Harry.  Had he done so, Harry could have clearly explained
    how the saddlebags would help him do his job (if that wasn’t obvious to anyone with a sound head on his
    shoulders . . . ).  If Ichabod still wasn’t convinced the bags would be a reasonable and effective accommodation,
    he should have explored other possible accommodations with Harry.
  • Moreover, Ichabod hadn’t taken the time or done the research to find out whether the cost of the saddlebags
    would be an undue hardship. Mere cost alone is often not an adequate “hardship” for a thriving business like
    Crane’s to deny an accommodation.
  • Ichabod fired Harry based on a myth or stereotype assumption about what a person with Harry’s disability
    – a detached head – couldn’t do instead of looking at what he could. Perhaps this is unusual for someone with
    a dismembered head, but Harry was still able to see and speak, as Ichabod had seen and heard for himself.
    Moreover, except for a few delayed deliveries which the bags would prevent in the future, Harry had been
    doing the job successfully for several days – proof that he was “qualified” for the job and could meet the nighttime
    drop off requirement with the aid of the saddlebags.
  • Ichabod rejected Harry’s requested accommodation for fear that others would want the same job aid. But how
    many headless workers does Crane’s have?  And sometimes under the ADA employers DO have to treat workers
    with a disability differently than others.
  • Even though Crane’s Midnight Messengers had good ADA policies in place, directing employees how to ask for
    an accommodation, the company failed to train its managers – including Ichabod himself – on the requirements
    of the ADA and how to handle an accommodation request. Investing in training is relatively inexpensive compared
    to the costs and business disruption caused by a single ADA lawsuit!
  • Finally, Ichabod failed to engage Matrix to help him through the tangle of ADA accommodations. (Obviously!)


MATRIX CAN HELP!  Matrix’s start-to-finish ADA Advantage management services can help you wrangle with tough issues like accommodation decisions, including leave assessment of leave of absence requests.  You always retain the final decision whether and how to accommodate, but we manage the intake, medical assessment, interactive process, recordkeeping, follow-up, and more.  Our expert team of ADA Specialist is at the ready with practical advice and expert guidance.  To learn more, spook to us at

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