I chose 2008 for the comparison over 2014 because I think the setup to the home stretch is more similar.
In 2014 the Brewers had a good start and led the division by as much as 6.5 games in early July.. But they lost 11 of 12 just before the All Star break to surrender that lead. They recovered for about a month to hold on to a small lead that did reach 3 games on August 17 Then they lost 8 of 10 to end the month to fall back into a tie heading into September. (Obviously the teams chasing them were not exactly tearing it up.)'
Starting September, though they were tied for first place, they looked like a team in free fall. Then they lost 8 of their first 9 in September to fall 6 games back, and it was all over. Going 9-16 in July and 13-14 in August didn't carry the mark of a champion. so, the 9-17 September was not that shocking. They finished losing 25 of their last 36.
In 2008, though, after a slow start, the Brewers had pulled to about 10 games over .500 when they made the Sabbathia trade just before the All Star break. After the break they reeled off 8 wins to tie the Cubs for first place. The four day massacre by the Cubs at Miller Park put a damper on hopes to win the division, so attention turned to the wild card race.
In August, the Brewers went 21-7 and though they couldn't gain ground on the Cubs, they went into September with a record of 80-56, second best in the NL, and 4.5 games ahead of the Mets and 5.5 games ahead of the Phillies. They only had to finish ahead of one of those teams for the one and only wild card spot because one of them would win the east.
The Brewers position looked strong and I don't think anyone anticipated what was coming next. The Brewers started the month getting swept by the Mets in a series at Miller Park. The next weekend they went into a 4 game series in Philadelphia still leading the Mets by .5 game, and the Phillies and charging Astros by 3.5 games.
After a 4 game massacre in that series that led to the panic firing of Ned Yost the Brewers were tied with the Philles and 1 game behind the Mets. They responded to the Yost firing by losing 4 of the next 5 and found themselves 2.5 games behind the fading Mets, who had surrendered the division lead to the Phillies.
We all know the ending. The Brewers won 6 of their last 7, including a 3 game home sweep over the last place Pirates, and 2 of 3 over the Cubs, who were resting players to get ready for the playoffs. to take the wild card from the Mets, who lost 5 of their last 8.
Anyway, the lesson from this is that a team that looks great in August can suddenly and unpredictably fall flat, I'm not predicting that the same thing will happen this year, but a long stretch of losing always begins with a short stretch of losing. It's important to keep that short stretch from mushrooming.
At least this year, with the expansion of the number of wild card teams, a spot in the playoffs is everything but mathematically guaranteed. But nobody wants to see the team limping into the playoffs like in 2008.