I'd be surprised if the answer to your question was other than 'the Phillies place an extremely high priority, possibly absolute, on staying below the cap'. Afterall, over the years, but with some continuing pieces of the original ownership families, this team has NEVER exceeded any cap guidance set by the Commissioner Whomever, whether on MLB salary budget or bonuses to draft picks. This is not a question of what the penalty is. They never exceeded the zero-penalty guidance on draft bonuses from the commissioner. This goes back to the history of the Phillies. Ruly Carpenter sold the team, because he was upset about rising player salaries and reduced absolute control of owners and commissioner. Bill Giles seems to have been picked to organize the new ownership group, precisely because he could be relied upon to continue Ruly's battle and be an automatic supporter of any move by the commissioner to hold down bonuses and salaries. Presumably, the Bucks were brought into ownership not only for their $, but because they could be counted on continue fighting what was regarded as the good fight. Middleton would have had to pass muster with this ownership group in order to be allowed into the boys' club.
One big factor that locks ownerships' of most of the teams and the league as a whole into neanderthal thinking on so many issues is the requirement that an owner must get approval to sell his team to a new owner. This means new thinking joining the ranks of owners can only occur when the commissioner and the existing owners make an error in sizing up a proposed new ownership group for a team that is being sold. It is a direct outgrowth of MLB's antitrust exemption.
The Phillies will never be the successful bad boys of baseball, whom the Yankees, Dodgers, and even the Braves are. They are such reliable toadies for the commissioner, that they don't even seem to get any benefits from their toadying.