Long before he was orchestrating trades as the general manager of the Red Sox, Brian O’Halloran was standing in front of the original Dunkin Donuts in Quincy, Massachusetts, hawking newspapers to make a few bucks.

The native of Weymouth, Massachusetts, sold copies of the Boston Herald and the Boston Globe as a child, then flipped the money for baseball cards on his way to accumulating a collection of more than 20,000 cards, which he’s donating to the Red Sox Foundation to raise money for social justice.

To add an important piece to the collection, there was the “trade of the century.”

“It was the equivalent of Derek Lowe and Jason Varitek for Heathcliff Slocumb,” O’Halloran said, referring to the famed trade by the Sox, who swindled the Mariners just before the trade deadline in 1997.

Long ago, O’Halloran and his older brother, Mike, had split a Domino’s pizza, but Mike had a significantly bigger appetite. Mike finished his allotment while his little brother was down to his final slice.

That’s when Brian made an offer.

“When I was really little, my brother is 2 1/2 years older than me, so one of his friends swindled me out of a bunch of my cards in the mid-70s for like a dollar’s worth of change,” Brian recalled. “I thought, ‘oh, money!’ So, I got swindled. Then I traded my brother, who didn’t really collect cards but had a few. I traded him the last slice of my Domino’s pizza for what turned out to be a Jerry Rice rookie card.

“I don’t have it anymore. I don’t know where it went. I’ve never found it. Maybe I deserved it. And I don’t know what it was worth at the time. But that was the trade of the century.”

It’s estimated that a Rice rookie card is now worth about $100 or much more, depending on its condition.

Like he often does as GM, O’Halloran was looking for long-term gain.

“That’s the one thing with a slice of pizza: there’s no way it’s going to increase in value,” he said.

Fast forward 35 years, and O’Halloran’s entire card collection is still tucked away in plastic tubs, mostly organized into boxes and binders by year, team and brand (Topps, Donruss and Fleer were among his favorites), and sitting in his basement.

Just before spring training this year, O’Halloran opened the closet and knew it was time to get rid of them. After noticing MassLive reporter Chris Cotillo donating his card collection to charity early in the pandemic, O’Halloran was inspired to do the same.

He had tried desperately to get his children into cards, but none of the three O’Halloran kids took the bait. They don’t want the collection, and neither does their old man.

“So I was like, ‘do I give these to someone, give them to charity? What are they even worth? I have no idea. Is that a good thing? Is that a burden on somebody?'” he said. “And then I saw Chris’s thing and now I have this GM title, which maybe helps. So I mentioned it to the folks at the Red Sox Foundation and they ran with it from there.”

The entire collection, which he believes includes most rookie cards from the late-70s and 80s, will be raffled off to one lucky winner next Thursday. Raffle tickets are bought with a donation to the Red Sox Foundation’s efforts for social justice, equity and inclusion. A $25 donation gets 10 tickets, a $50 donation gets 121 tickets and a $100 donation gets 300 tickets. The winner gets the card collection and a chance to spend time with O’Halloran.

“I don’t know, and kind of don’t want to know, what they’re worth,” he said. “I wouldn’t feel right about selling them. I don’t want them in the house anymore. They’re just taking up space. It seemed like a good way to do it.”

O’Halloran won’t keep any of the cards for himself, not even his favorites of Oil Can Boyd and Wade Boggs.

“I was a factory set guy,” he said. “I would get the Beckett guide and order stuff. It was pre-internet. I’d order a factory set, and if there were cards missing from a set I created myself, I’d go to the shop and go through the commons and try to complete the set. But I definitely have a bunch of factory sets I remember buying, mail order.

“And for that matter, there were a couple years you’d get the rated rookie cards and I’d buy like 100 of them. I never hit. I was a terrible evaluator back then. I bought a package of 100 of Ramon Martinez’s rookie cards. I should’ve bought his little brother’s, but I didn’t. That’s one of my evaluation mistakes.”

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