Ruben Amaro's Bogaerts fixation keeps Lee in Philly

Mike Ehrmann

A general manager's idée fixe sinks a deal that might have reinvigorated a decaying team.

The problem with making demands instead of negotiating is that sometimes you'll get what you want, but at other times you'll end up stuck with an ace when what you really needed was a handful of prospects.

Perhaps Ruben Amaro should be given partial credit for at least considering trading Cliff Lee at the deadline, but in the end the outcome seemed obvious to anyone who has followed Amaro's career: He would drive up the price, he would refuse to listen to offers that didn't include the buyer's best talent, and in the end he'd push away from the table and claim that he'd tried.

It seems clear the Red Sox didn't want Jake Peavy, at least not as much as they wanted Lee, but they defaulted to their backup plan instead of risking the clock expiring before they could grab an extra starter for the rotation.

For more on the Phillies and Red Sox, read The Good Phight Over the Monster

There are only a few people who truly know how the negotiations between the Phillies and Red Sox went, but if the third-hand accounts are to be trusted, Ben Cherington and the Red Sox were anxious buyers and understood that getting Lee would mean giving up top prospects in return. There was one clear caveat, however, and that's that the Red Sox would not part with shortstop Xander Bogaerts, the top- rated prospect in their organization. Naturally, that's who Amaro fixated on, the negotiations went nowhere, and the Red Sox moved on to the next best thing, a three-team trade with the White Sox and Tigers that sends Jake Peavy and reliever Brayan Villarreal to the Red Sox, Jose Iglesias to the Tigers, and outfield prospect Avisail Garcia, infielder Cleulius Rondon, and pitchers Francelis Montas and Jeffrey Wendelken to the White Sox.

Amaro might have a change of heart on the return for Lee after the Peavy trade happened, and there are still a few more hours to make a deal before the deadline, but the problem is that there's no obvious buyer now that the Red Sox have gone elsewhere for their pitching needs. Any roster would benefit from having Lee, a 34-year-old ace with playoff experience on their staff, but not counting the balance of this season, he's owed between $62.5 and $77.5 million (pending vesting options) over the next two-to-three seasons, and there just aren't many teams that have that kind of money and the prospect depth necessary to justify the trade. Lee is a great pitcher, the best on the market,and Amaro was partially right in asking for the moon in return, but the Texas Rangers or the St. Louis Cardinals, the only two teams that could afford such a deal without really leveraging the future, no longer seem to be in the market for starters.

This doesn't help Amaro shed his image, born out of the Ryan Howard extension and several misguided swaps, as one of the biggest dunces in baseball; poking fun at his decision-making is more en vogue than hating the wave or bunting. It's clear that many of the tales of his ineptitude are just hyperbole, but given the way he spurned the Red Sox it's easy to understand why these legends exist. It's not a question of whether or not the Phillies really needed to trade Lee (or Chase Utley or Jonathan Papelbon, for that matter), it's the fact that he made Lee available, walked up to the precipice of a deal that could reinvigorate an aging roster, then decided that the return wasn't enough to make the deal. That is a missed opportunity for the Phillies, who are not in need of a complete rebuild, but could benefit from some retooling.

Domonic Brown (Hunter Martin)

Though the Phillies have just a one-percent chance of making the playoffs this season, their struggles could be short-term. Next season, they will still have Cole Hamels, Ben Revere, and Dominic Brown. They also have Howard and Jimmy Rollins, who aren't going anywhere because of their hefty contracts. They are far removed from their MVP-winning prime but could still contribute to a winning team if surrounded by the proper cast. Minor league third basemen Maikel Franco and Cody Asche and left-handed pitcher Jesse Biddle could be ready to make contributions at some point next season as well. While the roster still has a few gaps -- they may lose Roy Halladay, Michael Young, and Chase Utley -- they still have a solid core and some payroll flexibility to offer players like Utley extensions or play in the free-agent market this offseason.

That roster is better with Lee on it, but it's also hard to ignore that the Phillies might have missed a perfect opportunity to clear some payroll, sell high on an ace, and reshape the future of the organization by getting players that could make an impact on next season's roster. Clearly Amaro saw that opportunity too, or else he wouldn't have even listened to offers on the ace.

Trading Lee would have given the Phillies more financial freedom in 2014 and 2015, as Halladay, Young, Utley, Rollins, and Mike Adams all potentially fall off of the payroll. There's also the elephant in the room, the frangibility of aging pitchers-though Lee has a clean bill of health and has averaged 225 innings per season in his 12-year career, it's hard to ignore that he's getting older and he's owed a lot of money. Lee, has never suffered a major arm or shoulder injury, but as with all pitchers there's the risk that he might not be as good tomorrow, two weeks from now, or next season.

It's hard to say definitively what the Phillies could have received in return for Lee, but it's reasonable to think they could have snagged at least a top-ten prospect and a couple of other players with upside. As one exec said yesterday (as per Joel Sherman), if the Red Sox and Phillies combined their minor-league talent into one Top-Ten list, nine of the best players on that list would be from the Red Sox organization. That may or may not be hyperbolic, but any objective assessment of the two systems suggests that the Phillies have only a smattering of impact-level talent while the Red Sox are flush with it; any combination of their talent in exchange for Lee might have been beneficial for the Phillies' future, even without Bogaerts included.

It's hard to know what names were mentioned in the negotiations, but it's not unreasonable to think that Jose Iglesias could have been a good long-term replacement for Jimmy Rollins, or that Jackie Bradley Jr. would have proved a dream upgrade over Delmon Young to join Revere and Brown in the outfield. Of Boston's top-ten prospects, half of them are starting pitchers that might have provided solutions in the absence of Lee and Halladay. The pieces are variable, but the premise is the same: When you consider the instant depth that this trade could have added to the Phillies' organization, it becomes a little easier to stop being sentimental and start being realistic about what roster improvements could have been realized by moving Lee, even if it didn't net Bogaerts in return. As good as Bogaerts might be, it wasn't worth spiting the whole roster if he wasn't available.

Four o'clock will come and go this afternoon, and Cliff Lee will still be with the Phillies. Aside from potentially moving Michael Young, the Phillies will keep their roster and their $160 million-dollar payroll intact, and they'll finish somewhere in the middle of the NL East this season. What isn't clear is whether or not Amaro's efforts will be enough for the team to compete next season. They'll still have their ace, but it remains to be seen if each time he pitches fans will be seeing a winning team behind him or the ghosts of young players who will now wear the uniforms of Boston, Detroit, and Chicago.

More from SB Nation:

Majority of Biogenesis-linked players to accept suspensions

Peavy headed to Boston in 3-team, 7-player deal

Phillies GM: Little chance Cliff Lee gets dealt

Michael Young will only accept trade to Texas

All our trade deadline coverage

Log In Sign Up

Log In Sign Up

Forgot password?

We'll email you a reset link.

If you signed up using a 3rd party account like Facebook or Twitter, please login with it instead.

Forgot password?

Try another email?

Almost done,

By becoming a registered user, you are also agreeing to our Terms and confirming that you have read our Privacy Policy.


You must be a member of to participate.

We have our own Community Guidelines at You should read them.


You must be a member of to participate.

We have our own Community Guidelines at You should read them.




Choose an available username to complete sign up.

In order to provide our users with a better overall experience, we ask for more information from Facebook when using it to login so that we can learn more about our audience and provide you with the best possible experience. We do not store specific user data and the sharing of it is not required to login with Facebook.