Rogers as team owner has an incentive to field a team which can make the post season, because it means home game attendees and the TV audience will still be interested in baseball at the end of the season.
Rogers doesn't have much incentive to field a championship calibre squad because they only have simulcast TV rights for the post season. The difference in cost between a playoff contender and a championship contender is less than the additional revenue generated. To win championships in the modern era, you need to have ownership which cares more about winning than return on investment. This is one of the reasons why the Baltimore Orioles look very formidable for the next several years - in addition to all the blue chip young, inexpensive and controllable talent they have in both the Majors and the minors, the new ownership group is headed by one of the richest men on the planet.