In the case of the Rays, they had a slow start, so if you were only betting on the Rays, you would have had a smaller bankroll when they started winning. This is why you end up with less money at the end.
For the Indians, their fast start meant you were betting more when they started losing, so again you end up with less money at the end.
However, this is not always the case. Some losing teams lose even more often as the season progresses. Some winning teams win more often as the season progresses.
Teams that "regress to the mean" as Tampa and Cleveland did only seem to do so because you find out the mean at the END of the season. The system I would like to try is one that shows expect W-L vs actual W-L, because perhaps the lines are overly weighted to the teams actual W-L. Surely this has been tried by now by many.