Sometimes one contract can ruin an entire market. It's not the player's fault, and certainly in this case the finger pointing shouldn't be pointed at Ryan Howard. But the Phillies screwed the market for at least a handful of teams with first baseman about to reach free agency this season or next.
Put it simply, his combined deals since he became an MLB player are almost identical to the one that Mark Teixeira received on the open market. Once he reaches his new deal in two years, he will probably be the second highest player in the MLB behind Alex Rodriguez (although who knows now, some much, much better first-basemen will hit the open market by then, and could surpass this deal).
As Rob Neyer put it, even in his best years, Ryan Howard is maybe, maybe one of the best 30 players in baseball, if you choose to look at a very specific set of stats. So what will happen when Adrian Gonzalez, Prince Fielder, and Albert Pujols approach free agency? This has to mean Pujols should get $30 million/year for 7 years, and Fielder should expect at least the same deal as Howard, even if he will be taking it at a younger age.
Howard should take up anywhere between 15%-20% of the Phillies payroll in the next several years. It also means they probably can't keep Jason Werth, who's primed for big money this offseason (Yankees or Giants maybe?). That's ok, because they have Dominic Brown, but it'd be better if they had Werth locked up up long term and could either trade Brown, Victorino or Ibanez away for a decent return (Werth will probably shake out as a "B" free agent, although he has a chance to grab an "A").
The Phillies should have waited, seen him declne as he aged, and used that as leverage. They probably could of at least shaved him down to $18 million a year. And they won't be able to keep Halladay either probably, as he'll want big money. The advantage of their big farm was they would have options as all their inexpensive talent became expensive. Now they're sticking themselves in a corner.
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