Formerly Of The Chicago Sun-Times

Quick update: I was informed today that I am no longer a Chicago Sun-Times columnist or contributor. So let’s spread the word on that. Sure, because I’d love for another publication to snap me up as the immensely hot property I am in time for me to debut with my coverage of next week’s Apple Event, but mostly because I’m certain that the Sun-Times would appreciate my doing that.

Where to, next? I dunno!

But here’s how I would describe my Dream Date:

  • I’m kind of a fan of being part of a larger outfit. I loved being a Sun-Times columnist (and will always be proud of the work I’d done there since 1999) and part of the fun was living up to the legacy of the great writers who came before me and were being published beside me.
  • I like health insurance and stuff, but freelancing is fine. I was freelance for the Sun-Times during my whole tenure.
  • Ability to publish with great agility. One of my few troubles with the Sun-Times was associated with understaffing. The editors are great folks who work very hard and are stretched quite thin, which often meant that my columns would take days to appear on the site. I’d love to be able to just write something quick and timely and have it in front of people shortly after I pressed a button on the CMS.
  • Willingness to publish long, thoughtful stuff, too. I’m only just now getting around to writing about this year’s smart speakers because (a) I didn’t want to be part of the initial marketing scrum and (b) it’s actually taken me a good while to figure out what I think. I have huge respect for my friends at iMore and other sites, whose skills are well-suited towards getting valuable coverage out there almost simultaneously with the events unfolding. My skills are elsewhere.
  • Nonetheless, I’m battle-hardened for getting out something quick in response to breaking news, and I would have published SO many quick 200-300 word bits for the Sun-Times if I had publishing privileges on the CMS. But! Honestly, I don’t want to have to know how many clicks something is getting, or be raked over the coals for not getting more of them.
  • I reserve the right to make up a word if I can’t fromate one that suits the immediate need of a sentence. This is where heroes step in and fix the inadequacies of the English Language.
  • And I’d like to receive enough trust that I can just provide X columns per week or month. I hate pitching. By the time I’ve convinced somebody that a thing is worth publishing, I could have already written it, and if I’m writing it, I want to get paid for it somehow. It’s a vicious circle.

I got my first regular magazine column in 1989. Ever since, my professional goal has been to do for tech what Roger Ebert did for movies. Yes, that was his beat, but what made Roger indispensable was his point of view. When the cast of an upcoming movie is announced, hundreds of sites scramble to post 300 copies of the same information. That’s fine. Roger wasn’t part of that land rush, though. Roger’s take on something was always worth reading, and there was only one writer who was posting it: Roger Ebert.

To do anything as well as Roger did is impossible. But my aspiration to consistently write with that kind of purpose, and to deliver that kind of value, will always be there.

The Sun-Times isn’t — wasn’t — my only source of income. I’m fine. So if I can’t find another columnist-type gig…who knows. Maybe I’ll just post stuff right here. It’s a solution that ticks all of the above boxes except for the first one. Maybe if I establish a routine here, I’ll look for sponsors. Or maybe I’ll give Patreon a go.

Or maybe I’ll become a ronin, honing my skills and purifying my spirit as I work for a series of outfits that need my swords for a specific task.

In any event! I send my thanks to all of my former editors at the Sun-Times over the past fifteen to twenty years. And I’m still tech contributor to WGBH public radio here in Boston, and I’m still co-hosting podcasts with my friends on MacBreak and Material.

And, yeah, if someone with a checkbook would like to step in before I do the unthinkable — publish my Chicago Apple Event coverage here, where I won’t get paid for it — please do get in touch:

(my last name) at

29 Replies to “Formerly Of The Chicago Sun-Times”

  1. I’d say you’ll be missed… but I’ll see you here, on TWiT and probably bump into you occasionally and make you wonder how you know me. All the best to you Andy!

  2. Bummer Andy. Hard to believe they would let you go after almost 20 years. I’ll keep listening to your insights on MacBreak Weekly and good luck in your future endeavors.

  3. I’ve been a fan since the mid-90s, and was inspired to become a journalist thanks in great part to your writing. I—and many others, I’m sure—will happily contribute to a Patreon, should you go that route. Thanks for all the excellent journalism at the Sun-Times and beyond.

  4. Long time admirer here and it’s been my pleasure to spend a few moments with you over the years, Andy.

    I’m optimistic for your next chapter and I know someone out there will appreciate the quality of your work and hire you.

  5. Living on the west coast, the Sun-Times rarely entered my consciousness except as a consequence of reading yourself or Roger.

    Now they will have no brain-share at all.

    Seems a strange move.

  6. I’ve followed your work for years and know you will land squarely on your feet. Changes of this nature always come with some amount of trepidation, but your fans are behind you and you are a great and unique talent. I, for one, am excited for what your future holds.

  7. Two ideas

    Ukulele tech journalist.
    Cleaning winders (stole from this clip)

    Your consistently a highlight of my week on MBW! I record preshow with python script off twitch!

    BTW, I have watched those ukulele clips from twit like 20 times over the years. It just makes me happy :)

    Also, neighbor of your former company’s HQ. think batwings


  8. I would just like to say that I am not an apple lover, but I watch Mac Break Weekly just to see/hear your comments and opinions. Rest assured I am becoming a Material regular, as well. Keep up the great content (as if you could do anything less) and keep your sense of humor.

  9. Well that sucks. It’s happened to me and there’s much I can say but you will find something and it will probably be a better gig. You’re sir are good at your profession.
    I’m just some random guy who listens to macbreak weekly and enjoys your honesty and metaphors so I hope this helps.

  10. Sorry to hear. But if they let you go they must be close to folding.
    I am not an Andriod fan, but I am a faithful listener of Material as you and Ion are a hoot.

  11. Andy,
    I’ve been watching your work for years. I’m looking forward to the next “thing” with anticipation.

  12. So sorry to hear that you are no longer with CST. It is a big loss for them. Luckily, I am able to keep up with you through Macbreak Weekly as I listen here over in Qatar. You and Leo have been a part of my life for a very long time.(virtually of course)

    Best Wishes.

  13. Hello Andy,

    I truly enjoy listening to you and the crew on MacBreak Weekly. Very informative and laughter on my part (you can’t hear).

    Hang in there. Ups and downs are part of the adventure of living. It gets better with time.

  14. I am reader, not someone with a chequebook, but I like your work, and found you via MBW.

    I like your work, please, keep everyone informed about how or where to find you, or how to help.


    Phil from Tasmania, Australia.

  15. Andy, I’m sorry to hear this news. You’re much more than a mere tech journalist. You think about the cultural and social impact as much as the micro-details of fresh gadgetry. If I could wave a magic wand, you would be installed at the New York Times. Seems to me your interests, integrity, and style would complement and enhance their mix of practical tips and analysis. Regardless, I have no doubt you soon will be snapped up by some fortunate publication.

  16. Sorry to hear that, Andy! I watch you all the time on MBW. Also listened to Ihnatko’s Almanac. Remember that when one door closes, another opens! I hope you find a gig at another publication sorry soon. Your talents are very much appreciated.

  17. I am sorry to hear this news Andy. You have always been my ‘go to’ expert for all things Mac! I, and many others, will follow you (and your work) wherever you go!

    I find it hard to imagine that you won’t be swooped up pretty quickly.

    Regards from Caleb Town,


  18. Dear Andy, I enjoy listening to you on MacBreak. Best wishes to you as you manage this transition.

  19. Sorry to hear this news, but I’m sure big things to come! Nice to meet you on the train yesterday.

    Onward and upward!

  20. Selfishly speaking, I am thrilled that I can finally read you on a regular basis. I have spent the better part of 5 years trying to find your work, only to be thwarted by the nefarious Sun Times web wall. I can now happily check in to this wonderfully active website and read with ease, one of the universe’s best loved tech journalist. I’d even be willing to throw in a couple of bucks each month if you had an easy way for me to do so.

    You are the best, and I wish you all of the wonderful things that you deserve.


    patrick michael denny

Comments are closed.