Looking at teams that have won 54 or fewer games (excluding strike years), how long historically does it take for them to:

1) Have a .500 or better season

2) Have a contending season which I will define as 86 wins in the wild card era?

I will confine my research to the free agent era (1976+).

1988 Atlanta Braves 54-106 … Got to .500 (94-68) in 3 years, got to contention level (94-68) in 3 years

1988 Baltimore Orioles 54-107 … Got to .500 (87-75) in 1 year, got to contention level (87-75) in 1 year

1977 Toronto Blue Jays 54-107 [expansion team] … Got to .500 (89-73) in 6 years, got to contention level (89-73) in 6 years

1979 Oakland A’s 54-108 … Got to .500 (83-79) in 1 year, got to contention level (64-45 in a strike shortened year which pro-rates to 95 wins) in 2 years

1998 Florida Marlins 54-108 … Got to .500 (91-71) in 5 years, got to contention level (91-71) in 5 years

1979 Toronto Blue Jays 53-109 … Got to .500 (89-73) in 4 years, got to contention level (89-73) in 4 years

1996 Detroit Tigers 53-109 … Got to .500 (95-67) in 10 years, got to contention level (95-67) in 10 years

2011 Houston Astros 51-111 … Got to .500 (86-76) in 4 years, got to contention level (86-76) in 4 years

2004 Arizona Diamondbacks 51-111 … Got to .500 (90-72) in 3 years, got to contention level (90-72) in 3 years

2003 Detroit Tigers 43-119 … Got to .500 (95-67) in 3 years, got to contention level (95-67) in 3 years

Summary:

There have been 10 teams in the last 42 years to win 54 or fewer games (5 of which won exactly 54; only 5 teams in that span actually won less than 1/3 of their games).

On average, the teams took 4 years to get to .500. But 7 of the 10 teams did it in 4 years or less, and one of the three that did not was a first year expansion team. The true outlier was the 1996 Tigers who went 10 years before getting to .500. Five of the 10 teams got to .500 within 3 years.

On average, the teams took 4.1 years to get back to an 86 win level that I defined as “contention”. Basically, just one team got to .500 (81 wins or better) but did not win at least 86 in the same year. So the results for “getting to contention” are pretty much identical to the results for “getting to .500”. Once again, 7 of the 10 teams got to 86 wins with in 4 years, and 5 of the 10 got to 86 wins within 3 years.

Only two teams out of 10, the ’89 Why Not Orioles under Frank Robinson, and the 1980 Oakland A’s under Billy Martin, were able to get to .500 the next season, and only the ’89 Orioles got to 86+ wins the next season.