Mandatory Credit: Evan Habeeb-US PRESSWIRE

Is Cliff Lee Ruben Amaro's Biggest Regret... Twice?

When the Phillies traded Cliff Lee away after the 2009 season for a collection of underwhelming prospects, it was a move Ruben Amaro would come to regret.

Because he jettisoned Lee to the Seattle Mariners, Amaro was forced to make a trade for Roy Oswalt in order to shore up the rotation for a playoff run in 2010. And while that was a good trade for the Phils, it would have been easier and cheaper if he had just kept Lee in the first place.

It’s a trade that appeared to haunt Ruben, because after the 2010 season, he stole Lee away from the Rangers and Yankees and signed him to a huge five-year free agent contract. It was a move that was celebrated throughout the organization and lauded by everyone who followed the team.

Now, just a year and a half later, Amaro is looking for a way out. The $87.5 million left on Lee’s deal, which takes him through the 2016 season, is a weight hanging around the Phillies’ neck, even more so with the extension deal for Cole Hamels and the four-year free agent deal given to Jonathan Papelbon.

And while Amaro didn’t trade Lee before last month’s trade deadline, and it’s unlikely he’ll move him prior to the August 31 waiver-trade deadline, Ruben has made it very clear that, if someone is willing to take on the rest of Cliff Lee’s money, he’s gone.

It seems obvious that, when all is said and done, Cliff Lee could be Ruben Amaro’s biggest regret as the Phils’ general manager.


He regretted trading him away to Seattle. That much was obvious when he signed him to a free agent contract just one year later. Now, he’d like nothing more than to unload Lee’s deal, realizing that he has too much money tied up in too few players to adequately address the rest of the holes on the roster.

Baseball is all about balance. Whether you’re at the plate, on the pitching mound, training, maintaining health over a long season, or constructing a roster, success is most often achieved when there is balance.

In this case, the Phillies are completely unbalanced when it comes to the makeup of this team. There is too much cash being spent on three spots in the rotation and the closer position. There is not enough money left to go around to fill in outfield, third base, and bullpen positions.

When the Phils won it all in 2008, they were a balanced team. The only ace they had was Cole Hamels. The rest were pitchers who were no better that #3-4 type guys like Myers, Moyer and Blanton. They won because they had a killer bullpen and talented, young positional players who could mash the ball out of the park whenever they wanted.

They had offense, great defense, terrific team speed, a phenomenal bullpen, and an ace starter who was on the most unbeatable streak of his career.

They had balance.

But that balance is there no more. Because he was chasing another championship, as we all wanted him to do, Amaro traded away young minor league talent and roster flexibility in exchange for a handful of veteran players who he thought would bring another parade down Broad Street.

But it hasn’t happened.

And that’s not necessarily Amaro’s fault. He’s done everything possible to put the best team on the field each and ever year. The playoffs are a crap shoot, and the Phillies have run into hotter teams each of the last three years. It is what it is.

But now that the credit card payments are due, Amaro looks at his roster and sees four players all making over $20 million a year starting in 2013. He sees the payroll commitments and realizes that, if he had a little more payroll flexibility, he could really do some damage and keep the playoff window open.

The Phillies need to do what the Eagles have done in transitioning from the McNabb/Westbrook era to the Vick/McCoy/Jackson era. They re-tooled without completely blowing up the franchise.

Sure, the Eagles have missed the playoffs occasionally over the last few years during the transition. That’s to be expected. And that is probably what’s happening with the Phillies in 2012. The core has gotten too old and too hurt, and an injection of new blood is needed. Sometimes you have to take a step backwards in order to take two steps forward.

And one of the ways that could happen is to trade Lee before the end of August or, more likely, try to find a suitor for Lee once the season is over.

It’s going to be a tough needle to thread, though. It’s hard to imagine Ruben eating a lot of Lee’s salary in any trade. It just doesn’t seem like the Phillies to pay $30 million for a player to pitch somewhere else. However, it’s all going to depend on what Amaro values more.

If Amaro values restocking the farm system with great young talent, then he’ll eat more of Lee’s salary. If his real goal is shedding the payroll, then the Phils may not get much back other than salary relief.

Of course, with Lee on waivers, there is a possibility that if a team were to claim him, Amaro could just let him go and allow the claiming team to take control of his entire contract, receiving nothing in return but payroll flexibility.

If that happens, Amaro’s priorities will be clear. But that scenario is unlikely.

What is most likely is that a team will claim Lee and Amaro will try to work out a trade and fail. Or, that Lee will clear waivers and Ruben will talk to a few teams about him, but will probably pull him back and hold onto him until the end of the season.

Don’t read anything into the fact that Lee has been placed on waivers. Most Major League players get placed on waivers, just so general managers have the flexibility to trade them if they want. Most players all clear waivers, and you never hear a thing about it. Lee being placed on waivers is not big news.

Once the winter rolls around, however, all bets are off. There is a decent chance Lee will get dealt. The only question will be how much of Lee’s contract Amaro is willing to eat, and what kind of prospects Amaro can get back as a result.

Either way, it seems obvious that, for the second time in his life, Ruben Amaro is regretting a decision he made with regards to Cliff Lee.

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