For 36 years, the 1988 Baltimore Orioles solely shouldered the burden of one of the American League’s most ignominious records. But on Monday night, when the Chicago White Sox lost their 21st straight game in Oakland, 5-1, they pulled even with the O’s for the longest losing streak in AL history.

Unfortunately for Larry Sheets,that only means twice the pain.

Sheets was one of the Orioles on that 1988 team, which lost 21 straight to open the season — a stretch that included the firing of manager Cal Ripken Sr. It was brutal, he said in an interview on Tuesday, “something I wouldn’t wish on my worst enemy.”

But then, it happened to his son.

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Gavin Sheets, a Gilman alum who plays outfield and first base for the White Sox, played in 16 of those 21 straight losses. Larry Sheets watches as many games as he can stomach, and when he talks to his son on the phone, he tries to dance around the subject of baseball. But Larry told Gavin on Monday, before the streak-tying loss, that he hoped the White Sox would avoid this unfortunate milestone.

“I told him, ‘How about letting me have this dubious distinction?’” Larry said, “You guys win and get it over with.”

Chicago’s struggles have dredged up bitter memories from Larry Sheets’ past — “a flood of emotions,” he called it. Though he played six seasons for the Orioles — including one transcendent season in 1987 when he batted .316 — he remembers the losing streak as a turning point in his career. When the Orioles fired Ripken Sr. and replaced him with Hall of Famer Frank Robinson, Sheets acknowledged his performance suffered. Ripken believed in him, but Robinson did not.

“I think it shows how fragile clubhouses are and how fragile professional baseball players are,” he said. “I lost my guy when Cal Sr. got fired after 6 games. I honestly believe we never would have lost 21 games if they hadn’t fired Cal Sr.”

A number of fluky things have to go wrong to lose 21 games in a row, especially with Cal Ripken Jr. and Eddie Murray in the lineup. A SB Nation retrospective on the 30th anniversary of the losing streak (”And why it will never happen again” a confident subheadline reads) detailed how losses piled up thanks to balks, pop-ups lost in the lights, and a weird plunge in performance with runners in scoring position.

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Larry Sheets shaved his mustache, one of his most distinguishing features, midway through the streak out of a superstitious hope that it might sway the ill fortune. But it made no difference to a clubhouse where self-confidence was at an all-time low. The Orioles would be leading late in games, and the clubhouse would wonder, How are we going to lose this one tonight?

“Thank goodness we had a game rained out,” Sheets remembered.

Catcher Terry Kennedy reportedly said halfway through the streak, “In 30 years or so, some team will be creeping up on 12 or 13 losses in a row. And by that point, we’ll be laughing. But we can’t laugh now.”

Larry Sheets certainly isn’t laughing. After all, Gavin Sheets isn’t just trying to win — he’s trying to show he’s still a capable major league player even on the worst team in baseball. Going 0-21 is a horrid start to a season, but even the ’88 Orioles won 54 games. Chicago is on pace to win 38.

“You really gotta dig deep, because with 45 games left in the year, it’s easy to let go,” Larry Sheets said of his son. “He’s gotta perform to stay there. In some ways, that’s even tougher to do.”

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Gavin Sheets, a Gilman grad, now shares a dubious history with his father, Larry: Both played on MLB teams that lost 21 games in a row. (Michael Reaves/Getty Images)

What makes the White Sox’s string of futility more bitter is how many former players are seeing success. Dylan Cease threw a no-hitter last month. Eloy Jiménez has enjoyed a strong start at the plate since being traded to the Orioles. On the current roster, besides Garrett Crochet, “nobody’s having a good year,” Larry Sheets said. It’s also difficult to play through the torrent of social media dunking on every Chicago loss.

But, Larry said, he told his son to hang on: “Hopefully this makes you stronger. If you can handle this, you can handle anything.”

Every losing streak eventually breaks. Chicago’s mercifully ended Tuesday night against the Athletics in a 5-1 victory. As of Tuesday morning, Larry Sheets hadn’t talked to his son yet, but added: “I know they’re happy it’s over.”

Sheets can relate. When the ’88 Orioles finally won their first game 9-0 — against, of all teams, the Chicago White Sox — it was a muted relief. Said Ripken Jr.: “’One-and-21? That’s not good. That’s not a reason to be jumping around and celebrating.’”

But the end of the streak was better received in Baltimore, which at the time only had one pro team to rally around. Sheets remembered either Gov. William Donald Schaefer or Mayor Kurt Schmoke bought the team a bushel of crabs. When they arrived back from their road trip to play their first home game at Memorial Stadium since their first win, there was a sellout crowd waiting to cheer them on against the Texas Rangers. They did win that night, 9-4.

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“We were fortunate,” Sheets said of the resilient fan support. “We were the only game in town.”

As time marches on, Sheets (who still coaches at Gilman) said it’s rare these days to hear from fans about the losing streak, as heavy as it weighed on the team and the city at the time. He’s more likely to hear about the rebound 1989 season, when the 87-75 Orioles finished just two games shy of winning the AL East — “We almost went from worst to first.”

Larry Sheets hopes that Gavin gets a chance to see a come-up in Chicago, as bad as things are right now.

“I will be happy for everybody in that clubhouse when it finally ends,” he said. “It was probably easier back in 1989 to build back quickly and compete, but it can be done. I’m hoping for the organization and Gavin that he’s a part of it. Just finish strong and see what happens next year.”