The contract in question- 5 years $125M.
*Ryan Howard is 31 years old. Still well within the age range of typical quality production, but likely has already maximized his growth/potential.
*He was set to become a free agent following the 2011 season. Same offseason that other slugging firstbasemen Albert Pujols, Adrian Gonzalez, and Prince Fielder were to hit the open market for bidding. The Yankees already have Mark Teixeira locked up long term at 1st, the Angels have Kendry Morales, and the Mets with Ike Davis. That leaves the Dodgers and Red Sox as big market teams that would bid on all 4. Essentially Amaro jumped the gun on the Howard extension and bid against himself.
*Since his magical MVP campaign of 2006 in which he clouted a 1.084 OPS, we've witnessed his OPS steadily drop over the past 4 seasons ('07- .976, '08- .881, '09- .931, '10- .859).
*Ryan Howard's WAR (Wins Above Replacement Player) was only 2.6 in '07, 2.8 in '08, and 2.1 in last year. Over the past 3 seasons he doesn't even crack the top 70 in the majors for WAR (this includes both batters and pitchers and takes into account position scarcity and fielding).
*Ryan Howard's defense remains subpar, mostly because of his inability to start a double play by throwing to 2nd base.
*Ryan Howard is below average against lefties- .232/.766.
*Ryan Howard is getting paid like a top-5 player. He has the 2nd highest contract in all of baseball by annual value, after only Alex Rodriguez’s bloated 2008 pact with the Yankees, and he has the 8th-largest contract by overall value. (Borrowed from UmpBump article)
*Slugging 1st basemen are a dime a dozen, just look around the Majors and you'll find a plethora of them- Pujols, Adrian Gonzalez, Fielder, Morneau, Huff, Dunn, Miguel Cabrera, Youkilis, Votto, Butler, Konerko, Teixeira, Pena, Berkman, and Morales that all have better or very similar OPS to Howard. And that's just players of his same position. Put him in the mix of every position and Howard's OPS hasn't cracked the top 15 in baseball any of the last 3 seasons, and ranks 19th overall during that span.
*Ryan Howard is a large man (6'4"/255), and by the time this contract is up he'll be 37 years old. Other big men of recent memory (Troy Glaus, Mo Vaughn, Cecil Fielder, Mark McGwire, Jim Thome, David Ortiz, and Frank Thomas) have not been able to remain offensive forces while playing the field (which Howard will have to do being in the NL), as they were able to DH or hardly play.
"This contract means that, over the first 10 seasons of his career, Howard will earn approximately $190.5 million. No player -- not A-Rod, not Mauer, not Derek Jeter, not Albert Pujols -- has equaled that number, in this or any other era."
Writer's Note- I enjoy watching Ryan Howard play this great game of baseball, especially in my favorite team's uniform. However, my fanaticism doesn't blind me and keep me from looking at things objectively.
*There's even been a blog dedicated to ridding the Phillies of Howard- Trade Ryan Howard.