It was one of those messages that made me want to dissolve into the chair and disappear.

The exact wording escapes me, but the note appeared in green type on my Atex computer terminal and went something like this: “Adam, tomorrow has one ‘m’ and two ‘r’s.”

I had just started working at the Boston Herald as an editorial assistant — or EA — in the features department in the late 1990s, and was tasked with putting together event listings. My main qualification was supposed to be a thorough knowledge of how to spell such common words as “today,” “tomorrow,” “Tuesday,” “Wednesday,” and so on.

I couldn’t even live up to that.

After a week on the job — which I started 20 years ago in January — I became both my boss’ biggest headache and the copy desk’s most unwanted responsibility. As baffled as those around me were as to how I made it through the three-day tryout period, I was nonetheless working there, had already moved out of my parents’ place and was on my own, sharing a one-bedroom apartment near Symphony Hall with two other 20-something adults. Making the job work was as big a deal as making my $240 share of the monthly rent. Never then could I imagine that I might one day see the Herald in the shape it’s in now, in bankruptcy court, facing either a discount sale or worse.

Given that I seemed to screw up everything I entered into my Atex machine, which among other modern functions lacked spell-check, I had little doubt I would be the first EA in the history of the Herald to be kicked out the front door and fired for profound incompetence. It would happen, I figured, in front of all those big-shot reporters, columnists, and editors, buzzing, yelling, and typing around me, knowing what they were doing all day while I sat there dumbfounded. I was sure that as I was getting fired, they would look up, chuckle and shake their heads, and then rush to file on deadline. My entire existence at the paper would be as insignificant as one of my overworked February event listings at Old Sturbridge Village.

But somehow the paper, either through union rules or pity or a combination of the two, let me stay on long enough to figure out what I was doing. At the time, not only could I barely type out days of the week, I couldn’t distinguish between when to use a semicolon and a colon; I had no idea what to do with that spiral-bound thing called the Associated Press Stylebook on my desk; and I could barely describe the difference between Faneuil Hall downtown and Faneuil Street in Brighton.

Not knowing where to turn, I borrowed and read nearly every book on writing and grammar the Boston Public Library had in its collection between 1998 and 1999: “The Art and Craft of Feature Writing,” “The Elements of Style,” “Simple & Direct,” and many others.

A big dictionary never left my side. I used it to look up any word with more than two letters in it.

Apparently I was learning. Editors started trusting me to write more and take on more responsibilities, and I could sense my prose was actually becoming coherent. I was hired by the arts section full-time as an editorial assistant not long after. Freelance writing became regular, and after penning a review of a Nine Inch Nails concert that my editor liked, I was given more concert reviews of heavy metal shows that nobody else wanted to cover, including an Ozzfest concert during which a muscular guy nearly strangled me for no reason.

I wanted to write so much that I spent all the money I made on these freelance stories on a cab ride home from the shows I reviewed (the trains wouldn’t run late enough to get me home), and then I’d rush to the 7-Eleven the night the stories went to press to see my work in print.

Knowing, however, that the Herald had a tradition of never hiring its editorial assistants as reporters, I left in 2001 to work at a community newspaper in Chinatown. That, I thought, was the end of my ties with the Boston Herald.

But it was actually part of an on-again, off-again relationship with the paper that would last until today. While I was never really more than a bolt in the Herald machine, and a replaceable one at that, I’ve ended up spending in total about 10 years working for the paper in one way or another: a few years as an editorial assistant, about five years as a part-time and full-time copy editor, several years as a freelance writer and, at times, as a freelance copy editor, and even once as a very temporary assistant editor in arts.

Now, as the Herald’s fate seems to be in the hands of others — a bankruptcy court judge and whoever might buy the paper — it’s hard not to feel a little bitter, sad, and even a bit of delusional hope that The Little Tabloid That Could just might come out better after all this is over. After all, if a screw-up like me could stick around at the paper so long, how impossible is it that the Herald could actually remain intact?

I have to admit, though, that this unfortunate time in the paper’s history did not come without warning. It also did not come without a significant period of waning.

When I started at the Herald, it was still a paper of personality and power. In fact, at the time it was investing thousands and thousands of words on a big exposé on Scientology. The five-part series stung the church so hard, it aimed a big PR campaign back at the tabloid. The paper was taken seriously.

Back then, the Herald was, unlike today, more than politics, sports, news, and sparsely edited Howie Carr columns. In many ways, the Herald was more than even a newspaper — it was its own journalism. And this way of journalism, even if you couldn’t describe it, drenched the pages in its black ink, no matter the section. Just take the arts pages. They could take on The Boston Globe’s and even the late Phoenix’s, but were unlike either. The section was serious business. Not only was there an actual staff that reviewed and covered music (even classical), television, movies, theater and exhibits, there was true curiosity and intellect. The little tabloid published thought-provoking stories examining the Museum of Fine Arts’ leap into pop art with a guitar exhibit dubbed “Dangerous Curves.” The paper may have had a tough side, but it was smart, too.

This was true as well in the paper’s once-proud business section. When I wasn’t working at the Herald, but at that Chinese community newspaper just blocks away and covering local development in the neighborhood, I would regularly check the paper’s real-estate stories. One of my favorite pieces was co-written in 2003 by my dear late friend and colleague Paul Restuccia, who, with reporter Scott Van Voorhis, exposed an obscure zoning tool called the “121A” that the city and big-money developers were allegedly abusing. Restuccia also helped the paper show the city the historic Gaiety Theatre, which would soon be demolished. The section won some prestigious journalism awards.

Even the angry right-wing regulars of the time — such as Don Feder, whom I had the pleasure of sitting next to for a while — read like gentle literary giants compared to the self-promotional, copycat line-up of today, one of whom even advertises herself as a model as well as, ahem, a writer.

But, in case you haven’t read the paper in recent years, and the circulation statistics say you probably haven’t, things have not been so good.

The stripped-down arts pages have offered less and less. The same goes for the business section. Even great news scoops by Laurel Sweet and other remaining veteran reporters for a long while would get pushed down the book for political coverage. And even in the few places where people remained, such as the photo department, the talent felt squandered.

What coincided with this downgrading across most sections was the loss of people, many of whom had worked at the paper for many years.

When I came back in 2008 for a part-time gig on the business copy desk, working mostly three to five days a week, the paper had suffered many losses, but familiar faces were around. That would soon change. After more buyouts and shakeups in the following years, more staffers would exit, especially reporters and editors of the business section that, slowly, starting around late 2010, disintegrated into a shell of its former self. (It would also strangely get renamed BizSm@rt. Yes, BizSm@rt. I can only imagine if I were an EA today, getting a message from an irate copy editor that reads: “Hey, peon sucker, BizSm@rt is one word, with a capital ‘S’, one ‘z’ and one ‘@’!”)

But for me, especially after 2011, things were actually going OK for a while. I was eventually hired full-time as a copy editor in the news section, and, suddenly, at this paper where I was once a complete shame and had questioned whether I actually deserved to cash my paycheck, I was now often writing 88-point headlines for news pages, and even designing pages 2, 3, 4 and 5.

It was a fun run.

Still, in 2013, I left the paper, almost certain it would soon be bought or close shortly.

But it didn’t fold, and I began to think it would somehow just stay afloat, literally, like some sort of jellyfish, bobbing along, sometimes ready to sting, but mostly just there.

By the time I came back to fill in for a weeks’ long stint at the end of 2014, writing TV reviews and editing arts stories, even more old-timers were gone, more desks were empty. Then I was asked to fill in some copy editing shifts for several months starting in mid-2017. That was the biggest shock. I was suddenly the stranger. Several of the desks that were actually filled were filled with new faces. The place just seemed eerily quiet. It was then that I felt the Herald was truly a different place. The changes had happened long ago, but now they were literally staring me in the face.

But it was running. The lights were on and the paper was getting printed. Even that radio station the paper devoted so much to was ostensibly on the air.

Now the road for the paper seems to have an end, or at least a big fork in it.

It’s hard for me to believe that whoever buys the Herald will keep the very few remaining veteran reporters, stellar photographers, and editors, at least not with comparable pay. Even those newer men and women at the paper, who over the past couple years had begun learning the ways of the Herald, will no doubt face a tough time. And no one is hopeful that the copy editors — those people who guard against slip-ups like those I made so many times when starting out — will remain, especially if GateHouse buys the paper and decides design work should go to Texas (where the difference between Faneuil Street and Faneuil Hall is on the top of everyone’s minds).

This is all bad news for the tabloid.

Still, when I see that iconic little Herald newsboy always clutching the paper in his raised hand, and think of the paper’s hits, good people and greatest headlines, I can’t help but believe that it might just surprise us all — if someone will just give it a chance.

Adam Smith is a freelance writer and copy editor who has worked for various publications, including the Boston Herald, where he currently pens two weekly real-estate showcases. He can be reached at adamsmith@tutamail.com.