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"Who the hell knows?" he said with a shrug.
That long ago memory resonates for the Phillies these days for a couple of reasons.
Among the points club president Andy MacPhail made during his media availability at Citizens Bank Park this week was he believed the farm system has an abundance of talent.
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"This is as deep an organization as I've ever been associated with," MacPhail said. "We don't have some of the marquee names that other organizations have. But in terms of depth, I think we're as good as there is in the game."
MacPhail also acknowledged the Phillies face the same dilemma as Dombrowski did years ago, as every baseball executive has had to deal with at some point: Knowing who to hold onto and who is expendable.
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"The simple truth of the matter is that while we might have 30 guys that we really think have a chance to get there, we might get six or seven out of that group," MacPhail said. "We're not smart enough to know which 22 or 23 aren't going to make it and which seven or eight are. We really aren't. But we try to do everything we can to push the odds in our favor of making a good decision."
No. 1: It's critically important that general manager Matt Klentak and his crew make the right decisions in deciding which players to keep.
MacPhail noted this is another area where advanced analytics will be part of the process.
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"This has been a passion of mine forever. Trying to understand what you have in the Minor Leagues," MacPhail added. "You can push a button now and access information, and a lot of that regards our young prospects. Which I always find fascinating. I'm always trying to rank them and put them in tiers."
The conventional wisdom is the Phillies' priority going into the offseason will be to add some veteran consistency to the rotation. That won't be easy.
"Everybody is looking for starting pitching," MacPhail said. "'Just get two quality starters and we'll be all set.' You might as well look for a unicorn at the same time."
While he conceded the organization may eventually have to take a big gulp and commit big dollars for a lot of years to an older free-agent starter whose best years could be behind him, he also pointed out that those teams often end up paying for past performance. That's a position he'd prefer not to be in.
Looking at the bigger picture, though, MacPhail said there might be indirect opportunities. While the free-agent class at the end of the upcoming season is considered somewhat thin, the group of players who could be on the market after the 2019 schedule has been completed includes Manny Machado, Bryce Harper, Charlie Blackmon and Dallas Keuchel.
As a result, there may be teams looking to shed salary in the short run to amass the funds to make a big free agent push later. Which in turn could make some attractive pitchers available who might otherwise not be. Which would likely mean having to part with well-regarded prospects.
"Is it possible that [Klentak] uses those assets in the Minor Leagues to augment our Major League club in '18? I think the answer to that is we definitely would consider that," he said.
No. 2: This is another strong confirmation the Phillies rebuild has reached an inflection point. Teams in the early stages of the process typically hoard prospects rather than trading them away.
Taking on expensive contracts from teams seeking to cut payroll for whatever reason is also another way the Phillies can use their deep pockets to improve the roster without diving head first into the upper levels of the free-agent market. Especially if the pitcher in question is established, but also younger, with less mileage on his arm.
There are a variety of ways to improve, and the Phillies are determined to explore all of them.
By the way, Dombrowski left the Marlins after the 2001 season to become president and chief executive officer of the Tigers. Two years later, with Beckett and Penny in the rotation, the Fish won the World Series.