Yes, I know they weren’t literally “always” winners. I should have qualified that to the time that I followed them, from the late 60s on. I began following them in 1967, and I basically was speaking of the last half-century rather than the previous half-centruy.

No, the Red Sox weren’t always winners. The Red Sox had a losing record for the 1920s, the 1930s, and the 1960s. The ’60s Red Sox before the Impossible Dream season of 1967 were pathetic. As old Case said many a time, you can look it up.

The all-time regular seasonal records of the Cubs and Red Sox aren’t all that different: winning percentages of .514 for the Cubs and .518 for the Red Sox.

https://en.wikipedia.org/wiki/List_of_Boston_Red_Sox_seasons

https://en.wikipedia.org/wiki/List_of_Chicago_Cubs_seasons

Perhaps you’re joking? If not, take a look.

Well, you don’t have to be so old for that.

But actually, unlike (for example) the Cubs, the Red Sox were always winners, even during the time when they never won the World Series. Much of that time they were in hot contention, often reaching the playoffs or even the Series, and then having some sort of spectacular meltdown or even one bad play that foiled them. They often came very very close but didn’t win the whole thing. That was what was especially frustrating about the Red Sox.