Use AI to improve your newspaper searching

I have loved online newspapers since my first free weekend trial on Newspapers.com, roughly a decade ago. And I’ll confess I thought I was pretty good at researching by this point. This week I learned there’s a big difference between pretty good and great. Here’s how you can get better results using any digitized newspaper platform and AI tool of your choice. In my examples I’m using Newspapers.com and the Glengarry County Newspapers.

I’ve had a paid subscription to ChatGPT for six months. If you’d like to start there, see “Me and ChatGPT, a story.”¹

I’m working on a case for an Irish Catholic family who emigrated to the Stormont (Cornwall), Glengarry, Dundas Co. area of Ontario in about the mid-1830s.² It’s a challenge, because many of the collections on which I rely, from passenger lists to vital statistics records, are unavailable, to say nothing of Irish census records. My goal is to find the previous generation somewhere in Ireland.³ The best record would be a Catholic marriage register entry for the progenitor couple but they may have married before emigrating or the Canadian church records may be missing.⁴ To support this case, I’m building a bunch of side trees for the Friends, Associates, and Neighbours (F-A-N) relationships – the sponsors and witnesses to the baptisms, marriages, and burials. At this point, I think I’ve done all I can with primary sources and am now on the hunt for secondary sources, such as family history books, genealogies, and newspapers.

Newspaper Searches

I’ll show you my results before and after using AI.

Here are the entries from my research log without AI assistance. I’ve located five nil/weak results.

Date	Site / repository	Search target	Result
22 Mar 2026	Newspapers.com	Obituary of James Donovan	Possible Kingston James Donovan, age 63, son of Richard Donovan of Ireland. Kept as a same-name possibility, but age and context were weak.
25 Mar 2026	Find a Grave	Burial of Richard Donovan at St. Raphaël’s	Nil useful result; no marker or clear burial clue.
1 Jul 2026	SDG and Cornwall Newspaper and Photo Digitization Project	Newspapers for the area	Repository identified for future searching, but no breakthrough result yet.
2 Apr 2026	Généalogie Québec	Random Cornwall-area obituaries	Nil for Richard Donovan, 1892, and Mary Donovan, 1889.
2 Apr 2026	Newspapers.com	Obituaries for Richard Donovan and Mary Ryan Donovan	Checked multiple January–March 1892 issues of The Freeholder and The Cornwall Standard; nil result.

And here are the results using AI. I’ve gone from five nil results to twelve relevant articles.

Date	Archive / site	Search target	Result	Why it mattered
7 Jul 2026	Glengarry County Archives	Richard / R. O. Donovan	Death notice for “R. O. Donovan,” father of Richard Donovan	Supported the 1892 St. Raphaël burial as the right elder Richard Donovan/O’Donovan.
7 Jul 2026	Glengarry County Archives	J. Donovan / Richard M. Donovan	Notice that J. Donovan of St. Polycarpe Junction visited brother Richard M. Donovan	Directly linked James Timothy Donovan to brother Richard M. Donovan.
8 Jul 2026	Glengarry County Archives	James Donovan / St. Polycarpe	Notice that James Donovan of St. Polycarpe Junction was in Alexandria	Reinforced James’s railway-linked movement between Quebec and Glengarry.
8 Jul 2026	Glengarry County Archives	Muriel Donovan	Death notice for James T. Donovan’s daughter Muriel	Confirmed the family’s move from St. Polycarpe Junction to Alexandria and documented a child’s death.
8 Jul 2026	Glengarry County Archives	Fred / Fred Jas. Donovan	Report of fatal C.A.R. railway accident at Coteau	Identified James Alfred Donovan as “Fred,” son of James Timothy Donovan and Mary Ann Sullivan.
9 Jul 2026	Newspapers.com	James Donovan + Canada Atlantic Railway	1883 appointment as train dispatcher at Coteau	Established James’s railway career much earlier than previously understood.
9 Jul 2026	Newspapers.com	Jas. / Jim Donovan	1883 notice: “Jim” Donovan visiting Cornwall, C.A.R. dispatcher at Ottawa	Confirmed nickname/name variation and railway employment.
9 Jul 2026	Newspapers.com	James Donovan + Casselman	1887 report: Canada Atlantic Railway agent at Casselman	Added a Casselman phase and showed he was respected locally.
9 Jul 2026	Newspapers.com	Fred Donovan + Coteau	Ottawa reports of fatal railway accident	Added details: first regular trip, special train to Ottawa, Water Street hospital.
9 Jul 2026	Newspapers.com	Mrs. James / Mrs. T. Donovan	Ottawa death notices for Mary Ann Donovan	Located her death at 507 Bay Street and her funeral route to St. Patrick’s and Notre Dame Cemetery.
9 Jul 2026	Newspapers.com	Mary Ann Donovan / Ontario death	Civil death registration located after newspaper clue	Added birthplace: Appleton, Ontario; confirmed death date and address.
9 Jul 2026	Newspapers.com	Joyce FAN names	Thomas, Ellen, and Margaret Joyce obituaries	Identified repeated Donovan sponsors as likely members of a Joyce family from near Wexford, Ireland.

Using AI to improve newspaper searches

I don’t know about you, but I get emotional searching newspapers. It’s a blend of excitement (what will I find), frustration (why can’t I find anything) and the sweet, sweet discoveries that keep me pinned to my computer for hours. This time, I asked AI to draft my searches. I did this by uploading my research to date, and then the site’s search parameters. (You know that page. It’s the boring one that talks about wildcards that you skip until you can’t find anything.) Within moments, AI gave me a list of searches and it was genius. All I had to do was copy/paste each search string into the search engine, review the results, and go to the next result. I had AI review the results and write citations for the log.

And I noticed with each new article we found, that new search variables revealed themselves.

For example, on July 7th, I found a notice “…that J. Donovan of St. Polycarpe Junction visited brother Richard M. Donovan.” This tiny article was a major clue because it said that Richard M. Donovan had a brother whose first initial was “J.” and who lived at St. Polycarpe Junction. Before finding this, I knew that Richard had a brother James, and that James worked with the railway, but I didn’t know where. Why is this important? Because an ancestor that is highly mobile is much harder to locate than an ancestor that stays put. Suddenly, I could add a search for “St. Polycarpe” to my list.

The next day, I located a second article that talked about James Donovan, of Polycarpe, which corroborated the first article. AI collected all the spelling variants for James: JT Donovan, Jas. Donovan, T. Donovan, J Donovan, James T Donovan. In two days, thanks to improved, AI-suggested searches, I found:

• the missing date and location of the death of Annie Sullivan, wife of James Donovan
• the detailed career arc of James Donovan, who rose from telegraph operator to despatch to station manager
• details about James’s family, from where his nieces went to school, to the fate of his son Fred Jas. Donovan
• the missing 1891 census, because the family was in Quebec (and not where I thought they’d be in Glengarry)

Example search – Glengarry Archives Newspapers

The free Glengarry County Newspapers site is a dream to research.⁵ The collection houses newspapers for the area and timeframe I’m researching (1880s onward), like The Glengarrian, and The Glengarry News. They have a helpful search tips page here.⁶ I gave AI the links to both pages and said, Using this site and these search parameters, give me a list of efficient searches for the Donovans.

Here is a snippet of the AI-created search for the Glengarry County Newspapers

Donov* AND issue:[1892-03 TO 1892-05]
“Richard Donovan”~5 AND issue:[1892-03 TO 1892-05]
“R Donovan”~3 AND issue:[1892-03 TO 1892-05]

Donov* AND issue:[1889-05 TO 1889-08]
“Mary Donovan”~5 AND issue:[1889-05 TO 1889-08]
“Mrs Donovan”~5 AND issue:[1889-05 TO 1889-08]

For example, Donov* AND issue:[1892-03 TO 1892-05] means: search for any name beginning with “Donov” in the issues March through May, 1892. “R Donovan”~3 AND issue:[1892-03 TO 1892-05] means: search for the name “R Donovan” within three words in the issues March to May 1892.

I did this for each of the surnames on my list. Eventually, I ran out of name-based searches and said, Let’s do a non name-based search using addresses, locations, and subjects. AI gave me this list. And the best part? Because I’d been using AI to analyze, transcribe, and write citations, it knew the updated search terms.

“Glen Roy”
Glenroy
“Dominion St”
“Dominion Street”
“St Polycarpe”
“St. Polycarpe”
“St Polycarpe Junction”
“Coteau”
“Coteau Junction”
“Bay Street” AND “Gladstone”
“504 Bay”

That was the end of the first day. The next day, I thought, why not try this with Newspapers.com?

Why search more than one site for newspaper articles?

Q: Why would I bother repeating the entire exercise on a different website?

A: Because each site might have different results. They might have the same titles but different years. They might have different titles. They might have the same titles and the same years but the search functionality might be better on one site than the other. For my Cornwall family in the mid-19th century, I wanted as complete a run of the earliest titles as possible and Newspapers.com carries a good range of papers. See below.

Newspaper	Coverage	Why it matters
The Freeholder	1883–1928	Best target for Richard Donovan’s 1892 death, Mary Ryan Donovan’s 1889 death, James Timothy Donovan’s railway notices, and Cornwall-area family news.
The Cornwall Standard	1886–1932	Essential companion paper to The Freeholder; should be checked for the same events because one paper may report what the other misses.
Cornwall Reporter and Eastern Counties Gazette	1876–1879	Shorter run, but useful for older Donovan children, land/community notices, and pre-1880 context.
Cornwall Freeholder	1928–1932	Useful bridge after The Freeholder run ends.
The Standard-Freeholder	1932–1941	Useful for descendants, obituaries, marriages, and local follow-up.
Daily Standard-Freeholder	1941–1960	Useful for twentieth-century descendants.
Standard-Freeholder	1960–2008	Mainly descendant and modern obituary work.

As the search progressed, I realized I’d been too narrow in my thinking. My James Donovan lived in Ontario (Carleton, Casselman, Cornwall, Glengarry, Nepean, Orillia, and Ottawa), Quebec (Coteau and St. Polycarpe) and Manitoba. Why is this important? Because it affects the searches. If I didn’t know about his movements, I would not search for him outside Glengarry, or Ontario for that matter, or worse, I wouldn’t recognize articles that were about him but I thought were someone else.

Example Search – Newspapers.com

I gave AI the link to Newspapers.com and a few help pages for how to search. AI knew this website was different from the Glengarry County Archives and modified its search terms. Here is an example of searches for James Timothy Donovan.

“James T Donovan” railway
“James T Donovan” “station agent”
“James T Donovan” “St Polycarpe”
“J T Donovan” “St Polycarpe”
“J T Donovan” “St Polycarpe Junction”
“James Donovan” “St Polycarpe Junction”
“J T Donovan” “Canada Atlantic”
“J T Donovan” “C.A.R.”
“James Donovan” “Coteau”
“James Donovan” “telegraph operator”

And here is a list of AI-generated search terms that are not name-based.

“St Margaret’s Convent”
“St. Margaret’s Convent”
“Xmas Examinations”
“December Examination”
“Macpherson and Schell”
“veneer department”
“Canada Atlantic Railway”
“St Polycarpe Junction”
“Coteau Junction”
“Water Street General Hospital”
“fell between cars”
“Green Valley station”
“taken up land”
“Glenroy Dairy”
“Catholic Mutual Benefit Association”
“C.M.B.A.”
“Branch No. 201”
“Alexandria Fire Brigade”

And that is how I ended up with a dozen relevant articles for the family I’m researching. I may not know James’s grandparents yet but I’ve got a lot more material to work with.

An AI prompt you can try

Here is a prompt you can try with your own AI of choice. If you don’t have a research log or report ready, start by giving all the details you know.

You are helping me search historical newspapers for genealogical research.

My research subject is:

Name:
Known name variants, nicknames, initials, and spelling variants:
Date range:
Places lived, worked, visited, or had family:
Occupation(s):
Employers, organizations, churches, schools, clubs, lodges, military units, or other affiliations:
Spouse:
Children:
Parents:
Siblings:
Known addresses, farms, lots/concessions, streets, or neighbourhoods:
Major life events:
Known associates, neighbours, witnesses, sponsors, pallbearers, or in-laws:
Newspaper site I am using:
Known search features of this site, such as phrase search, wildcard, proximity, Boolean, date filters, location filters, OCR quirks:

Task:
Create a practical newspaper search strategy for this person. Do not search only the full formal name. Use the facts above to generate searches based on names, initials, nicknames, occupations, employers, places, relatives, addresses, events, and associates.

Organize the searches into categories:

1. Core name searches
2. Name plus place searches
3. Name plus occupation/employer searches
4. Family-member searches
5. Address or property searches
6. Event-based searches, such as marriage, death, accident, lawsuit, presentation, farewell, illness, school, church, business, or travel
7. FAN-club searches using associates, witnesses, sponsors, neighbours, and in-laws
8. Negative/same-name control searches

For each search, explain briefly why it is worth trying and what kind of result it might find. Also suggest which searches should be tried with quotation marks, wildcards, proximity operators, Boolean operators, or date/location filters based on the search features of the site.

Afterword

In genealogy there are a hundred ways to spend money and we all need to be judicious about what subscriptions we need. Now that I’m paying for Chat, I’ve been finding ways to incorporate it into my daily genealogical processes, and having a great time while I’m at it. I use ChatGPT Plus but you can use whichever AI platform you prefer. For today’s blog, I couldn’t wait to share my newspaper search tricks with you, to come up with better ways to research.

I also used AI to help me with this piece, but not the writing. Nope. That’s all mine.

Thank yous

Thanks this week goes to my client, who has trusted me to dig deeply into his family’s roots, and sometimes share the stories.

References

1. Linda Yip, “Me and ChatGPT, a story,” 21 Dec 2025, blog, Past-Presence.com. ↩︎
2. Thank you to the client for permission to share the details of his family’s genealogical case with you. ↩︎
3. There are online trees for this family but credible, supported documentation is thin. ↩︎
4. There are nil marriage records for Richard Donovan and Mary Ryan, who possibly married in the Cornwall area before 1838. They appear to have preferred St. Columbans, but to be sure I’ve also checked nearby parishes such as St. Andrews West and St. Finnans. Ontario Irish Catholic records are available at both Ancestry.com and Généalogie Québec, but the years I need (roughly 1830-38) are incomplete at both the diocesan and parish levels. ↩︎
5. Glengarry County Archives: Digitized Newspapers, database with digital images, https://newspapers.glengarrycountyarchives.ca/ : accessed 9 July 2026. ↩︎
6. Glengarry County Archives, “Help,” Glengarry County Archives: Digitized Newspapers, sections “Searching” and “Additional Search Operators,” https://newspapers.glengarrycountyarchives.ca/help : accessed 9 July 2026. ↩︎