The Chicago White Sox are so bad that relief pitcher Michael Kopech gained nearly 40 games in the standings when he was traded to the Dodgers a week ago.

The White Sox are so bad that they could finish with the worst record of any team since 1900. Their winning percentage of .23478 (27-88) is below that of the two teams long considered the most wretched — the 1916 Philadelphia Athletics, who finished at .23529 (36-117), and the 1962 New York Mets, who finished at .250 (40-120) in their expansion season.

The White Sox are so bad that manager Pedro Grifol‘s record is 101 games under .500 (88-189) in less than two seasons through Monday’s games. Perhaps Grifol shouldn’t fret too much: The managers of the 1916 A’s and 1962 Mets were Connie Mack and Casey Stengel, respectively, both enshrined in the Hall of Fame.

Yet Grifol can’t help but worry. With 21 losses in a row, his White Sox have equaled the American League record set by the 1988 Baltimore Orioles, whose ineptitude is particularly shocking considering future Hall of Famers Cal Ripken Jr. and Eddie Murray played every game that season.

Next up is the MLB record of 23 consecutive losses set by the 1961 Philadelphia Phillies. And, yep, they also boasted a future Hall of Famer in pitcher Robin Roberts, whose 1-10 record was an outlier in a 19-year career that included six consecutive 20-win seasons.

Excuse Grifol for not wondering whether he has a future Hall of Famer somewhere on his roster. He’s consumed by losing.

“We talk about it every day, everybody knows what it is,” he said. “It’s 21 in a row, it sucks, it’s painful, it hurts, you name it.”

Here’s a look at teams that lost at least 20 in a row in a single season:

— 1961 Phillies, 23 in a row: Their streak lasted most of August and the Phillies finished 47-107 in 35-year-old manager Gene Mauch‘s second season. Mauch righted the ship in 1962 and the Phillies posted winning records in each of their next six seasons.

— 1988 Orioles, 21 in a row: With Cal Ripken Jr. at shortstop and Billy Ripken at second base, manager Cal Ripken Sr. was fired after the Orioles began the season 0-6. The losing didn’t cease, however, with their first victory not coming until April 29. They finished 54-107.

— 1969 Expos, 20 in a row: Mauch presided over another historic losing streak, this one going from May 13 to June 7 in the Expos’ first MLB season. Future Angels general manager Bill Stoneman was the staff ace, although he took the loss five times during the streak. The Expos finished 52-110.

— 1943 and 1916 Athletics, 20 in a row: Mack (not Mauch) staggered through a desultory August 1943, that included 24 losses in the last 25 games of the month. Mack was 80 years old but lasted another seven seasons before retiring, having managed a record 7,755 games and winning five World Series. Mack was 53 when he endured a 1916 season in which the Athletics never won more than two games in a row.

— 1906 Boston Americans, 20 in a row: May was miserable for the Americans, who changed their name to the Red Sox after the 1907 season. The losing streak began May 1 and didn’t end until May 25. Five of the defeats went to 39-year-old Cy Young, who led the AL with 21 losses but rebounded to post 60 wins over the next three years. Player-manager Jimmy Collins — another future Hall of Famer — deserted the team July 1 and went from revered to despised in Boston. The Americans finished 49-105-1.