
I began my Monday before Thanksgiving sitting on the subway, when a chirpy “Hello, Santa!” got my attention. A four- or five-year old boy, sitting across from me on a woman’s lap, waved at me. Next to them sat a girl of perhaps seven. I caught the adult’s eye. She smiled, so I answered and asked if he had been good. He assured me he had been very good, at which the girl rolled her eyes. I asked her if the boy I now assumed to be her brother was telling me the truth. She responded that she had been much better, and then we had a conversation for a few stops about what they’d like for Christmas — we settled on a set of building blocks that made “a lot of noise when I knock them over” for Charlie, and a copy of Charlotte’s Web for his sister, Alexis.

“Hello, Santa!” once again got my attention, this time from what appeared to be an older street person, a woman of indeterminate age in a tweed overcoat that had seen better days. I returned her greeting and asked how she was. “I’m hungry,” she said.
Usually at this point, I would reach into my cargo-pants pocket reserved for just such encounters, give a dollar bill folded into an origami tee shirt and wish the recipient a good day. But the Santa identification struck me as out of the ordinary. I thought of a friend of mine, a rather distinguished poverty program analyst, who always responds to requests for money for food with something nutritious, purchased on the spot at the nearest deli or grocery store. We were outside a McDonald’s, so I offered to buy my new friend Evelyn a meal. She accepted, and while we were waiting on line, told me a bit of her story.
Her living situation was rather complicated, involving a daughter-in-law she didn’t particularly like and an agreement to be out of the apartment during the day. She sometimes stayed overnight with friends, sometimes at shelters — primarily to annoy her son — and asked for money on the streets to pay for lunch and an afternoon snack Some days were better than others. It was mostly the cold she didn’t like.
Back again on the subway, I pondered my interesting Big Apple kind of day. “Worthy of, at least, a submission the Times’ Metropolitan Diary,” I thought. And then it hit me — we were paused at the Herald Square stop, the home of Macy’s and the Miracle on 34th Street.
So, I went home and applied online to be a Macy’s Santa. Here’s what I learned:
Responsibilities
- Having my picture taken lights me up and makes my cheeks glow
- Creating the Santa magic for others would bring me joy
Qualifications
- A well-groomed, natural beard, welcoming smile and bright eyes characterize me
- Being described as a “jolly old fellow” would be a compliment.
- Abilities to perform entertain and sing loudly for all to hear are talents (not required)
- Flexibility to work full-time, part-time or as needed
- Minimum age 18
- Must be available 7 days a week, 9:30AM until 4 PM
- Maintain a well-groomed beard, naturally white or artificially whitened during season
- Excellent personal and dental hygiene with ability to smile frequently
- Always remaining in character while on location and within public view
- Email address with ability to correspond and complete paperless onboarding process
- Must have reliable transportation
- Ability to walk and stand independently
- Ability to sit for extended periods and often change positions between sitting/standing
- Ability to often lift and/or manage holding 10-25 lbs
- Ability to read and speak English
- Adherence to all policies and procedures outlined in Employee Handbook with specific attention to employee’s responsibility for tracking all hours worked using method provided and following all safety procedures
I answered all the questions in the affirmative.. I attached my corporate resume, a connection to my Amazon book page, along with a personal statement that included a reference from the director of a preschool in which I’ve teach origami and found-object sculpture. And I added a PS that I was sure would clinch the job:
Among an extensive history of strange and wonderful jobs, I was a Cuisinart demonstrator at Macy’s back in 1984. Ask me about Raspberry Fluff, which I learned from Martha Stewart herself, just starting out as a cookbook author and recipe developer.
And just to be clear, when you ask about “reliable transportation,” do you mean other than my reindeer-driven sleigh?
I got an immediate reply:
Hello James Gaynor,
Thank you for your interest in joining our team! We just received your job application for our Seasonal Santaland – Santa Claus, Herald Square – Full Time (TEMP).
We are currently in the process of reviewing your eligibility, experience, and qualifications for this position and will have a response for you shortly — so watch your email closely for updates!
In the meantime, please follow us on Facebook, Instagram and LinkedIn for the latest news on job opportunities, career resources, and hiring events. We truly appreciate the time you’ve invested in the application process and for considering us in your job search.
Warm regards,
Macy’s Talent Acquisition
An interesting side development is that I now have a new BFF, Artificial Intelligence Phil, from something called ZIP. He contacted me, saying that he had seen my Macy’s application, and wanted to know if I had my own wire-rimmed glasses and boots. I told him that I did, and he responded with some alternative job possibilities that included Car Detailer, License Plate Reader Coordinator, Security Screener and Veterinarian.
I’m still waiting to hear from Macy’s.

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This post is republished on Medium.
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Photo credit: iStock

If I ran Macy’s you would be sitting in the Santa seat right now.
Reindeer transportation or no, 34th Street is definitely a challenge!
NOT delightful. Just kidding! DELIGHTFUL!
HA–Great story! Macy’s loss this year–I would have hired you, James! There’s always next year….;^)
HaHaHa!!!! Or shall I say HoHoHo???
Maybe we should package ourselves as a team…… I can be your elf-in- residence…….
I love this !! You would be perfect for this job and as always your wit is undeniable. That’s a fantastic picture of you at the end. The photographer captured your true essence !
from the way you’re dressed in that final picture, you might have more success if you applied for a Santa position in San Marcos [“Bananas”]
DELIGHTFUL!!
Well done, Jim! Since it’s almost Christmas, it may be too late to be selected as Santa. Why don’t you find out when they start accepting applications and apply for next year. You’d be a wonderful Santa!
Well, done, Santa! (Love the “Community Watch Santa” mufti.) You are truly well-suited to this task….
Santa on the Subway! I don’t watch the Hallmark holiday movies, but this essay could easily be a hit. And thank you for feeding a hungry soul. I’m curious. On your application did you list Kris Kringle as your nickname?
Wow! Jim really knows how to live a New York life!
This is a great example of getting into the spirit of the festive season! New York City again another compelling character starring in a story of self-discovery.
James never fails to make me smile if not laugh out loud! Wit and charm with a penchant for memorable realities are his calling card. I own all of the books he has written so far and look forward to his next epistle. He often reminds me of a few words from a favorite Christmas carol – “Comfort and Joy.” Bravo as always James. You make a great Santa!
Delightful! I’m confident the author would make a fantastic Santa, and he seems to have a great report with the public! May I be your elf?
Delightful! Santa Claus as Curtis Sliwa! I liked every bit of this article and look forward to seeing whether James Gaynor becomes the Edmund Gwyn (sp?) of our millennium. Who will play Natalie Wood remains to be seen. And Artificial Intelligence Phil needs to be led on the merriest chase of them all.