By Jay Jaffe
July 30, 2012

Cliff Lee, a former Cy Young winner, has already been traded four times in his career, including three times since 2009.

It's been a lost season for the Phillies, who appear likely to miss the playoffs for the first time since 2006. With Ryan Howard, Chase Utley and Roy Halladay all losing significant chunks of time due to injuries, and Shane Victorino and Jimmy Rollins not producing up to their career levels, Philadelphia has occupied the NL East cellar for all but a few stray days since the first week of May. Swept by the Braves over the weekend, the Phils are just 18-32 since the calendar flipped to June, and 45-57 overall, 12 1/2 games back in the Wild Card and 16 1/2 back in the NL East.

Last week, the Phillies agreed to a six-year, $144 million extension with Cole Hamels, who likely would have fetched the largest haul of any player on the trading block. The details on his deal haven't been released, but he'll make an average of $24 million per year from 2013-2018, which means that the team now has around $134 million committed to seven players for next year — all of the aforementioned except Victorino, plus Jonathan Papelbon and Cliff Lee — and around $100 million committed to five players for 2014. The rumor mill is now abuzz with the possibility that general manager Ruben Amaro Jr. is willing to deal Lee, a move that would greatly improve the team's flexibility in the coming years, and help compensate for a farm system that's been hit hard by trades in recent years. That is not to say, however, that replacing a pitcher of Lee's caliber in the rotation will be a snap.

Lee finished third in the Cy Young voting last year behind Clayton Kershaw and Halladay, but the 33-year-old southpaw has had a rough 2012 season, going 1-6 with a 3.95 ERA and missing three weeks due to an oblique strain back in April and May. He's still striking out 4.9 hitters for every one he walks — good enough to rank second in the league — but his 1.1 homers per nine are his highest rate since his dismal 2007 season, while his .321 batting average on balls in play matches his gaudy 2009 mark. He has struggled particularly with men on base, yielding a .340/.367/.532 line keyed by a .381 BABIP in such situations. The loss of Utley, an elite defender who didn't make his 2012 debut until June 27, likely has had something to do with that; even with his return, the team ranks 13th in the league in defensive efficiency at .681, nine points below the league average.

Lee is now in the second year of the five-year, $120 million deal he signed with the Phillies in December 2010. He's making $21.5 million this year, but his salary jumps to $25 million a year from 2013-2015, with a $27.5 million club option for 2016 and a steep $12.5 million buyout. According to the information at Cot's Contracts, that option becomes guaranteed if Lee is not on the disabled list at end of the 2015 season due to an injury to either his left elbow or his left shoulder, and if he totals 200 innings in 2015 or 400 innings in 2014-2015. Even before considering the fact that he has limited no-trade protection that enables him to block trades to all but eight teams, such a contract would be a difficult one to move given the $87.5 million remaining beyond this year. The Yankees and Rangers are among those eight teams, but the former, who were jilted by Lee back in 2010, don't appear to be in the mix given long-term budget constraints that have them aiming to avoid paying a steep luxury tax penalty in 2014.

The Rangers, who acquired Lee in July 2010 and rode him all the way to that year's World Series, appear to need a frontline starter, having been shut out in their quest for either Hamels or Zack Greinke, and having seen their pitching depth take several hits in recent days. They lost Colby Lewis for the season last week due to a torn flexor tendon, scratched Roy Oswalt from his scheduled July 23 start due to lower back woes and scratched Neftali Feliz from a minor league rehab start on Sunday due to elbow soreness. Thus far, they have balked at the price for Grienke (since dealt to the Angels) as well as next-tier starters such as James Shields and Josh Johnson because of their unwillingness to deal Mike Olt, a 23-year-old third baseman who ranked 43rd on Baseball America's Top 100 Prospects list coming into the season, and who is hitting .291/.404/.582 at Double-A Frisco. With Adrian Beltre under contract through at least 2015, Olt would need to shift positions in order to crack the Texas lineup, making him more valuable as a trade chip than as a future Ranger.

With Placido Polanco a free agent after this season, the Phillies are in search of a long-term solution at third base, and Olt would fit the bill. They've got other glaring needs they'll need to fill after this season as well, as Victorino and leftfielder Juan Pierre are both free agents who are likely to be dealt before the deadline. Rightfielder Hunter Pence has been marketed even more aggressively than Victorino according to at least one report; he's under club control for next year, but is expected to command a salary in the neighborhood of $14 million — that's on top of the aforementioned $134 million payroll figure. With John Mayberry Jr. scuffling at the major league level (.230/.269/.385) and former top prospect Domonic Brown hitting a tepid .292/.340/.440 at Triple-A Lehigh Valley after missing a month due to a knee injury, Amaro will need to go outside the organization to obtain at least one outfielder this winter, preferably somebody who can ease the offensive burden on the aging core of Howard (who is 32 years old), Utley (33) and Rollins (also 33). Philadelphia will also need to replace Joe Blanton in the rotation (the pending free agent is rumored to be close to being traded to the Orioles at this writing), with swingman Kyle Kendrick representing a fallback solution at best.

The two major wild cards in the trade-Lee equation are how much of his remaining salary the Phillies would need to eat in order to receive multiple top prospects in return, and the condition of Halladay. The 35-year-old righty, who missed seven weeks due to a strained latissimus dorsi, has posted a 4.33 ERA this year, his highest since his record-setting double-digit ERA in 2000. His peripherals are strong (0.9 HR/9, 1.6 BB/9, 7.3 K/9), but his velocity has dipped as he has gotten into bad habits with a lower arm slot, lessening the effectiveness of his cutter. As a result, he too has been hit hard with men on base (.298/.341/.460, driven by a .351 BABIP). Halladay is guaranteed $20 million for next year, with a $20 million club option for 2014 that becomes guaranteed if he throws 225 IP in 2013, and 415 IP in 2012-13 — unlikely given his 89 1/3 innings to date this year — and doesn't end the 2013 season on the disabled list. If he can regain his old form to form a strong one-two punch with Hamels, and if Amaro can upgrade an offense that ranks ninth in the league in scoring, the team can probably afford to round out its 2013 rotation with something less than another ace.

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