Indulging: Cliff Lee For Justin Upton?

It was something a lot of us could sense, but not necessarily put our fingers on. The Phillies had been very quiet this offseason, linked in name to some outfield options only to see them be inked by other clubs. Then, just before 5 p.m. eastern Wednesday, Pedro Gomez unleashed this:

Now isn’t THAT something?

Now, Gomez is not typically known for his baseball news-breaking and the report was, as expected, shot down not long after by other reporters and (rather vehemently) by Amaro himself. So, knowing that this deal is nowhere near imminent and perhaps nothing more than a breath beyond “rumor,” let’s press on and ponder the hypothetical.

Removing personal attachments and viewing these players simply as baseball assets, the fit would seem to make sense for both sides. In Justin Upton, the Diamondbacks would be parting with a homegrown, cornerstone player who turned 25 in August, a right fielder that the Phillies had hoped Domonic Brown would one day be. In Cliff Lee, the Phillies would be parting with a 34-year-old ace who has posted excellent numbers each of the last five years, a formidable counterpart to Ian Kennedy, Daniel Hudson and, potentially, Trevor Bauer.

Each part of the deal carries risks complementary to their rewards. Could the Phillies deal from a supposed position of strength, with Roy Halladay’s health in question and immediate “prospect” replacements far from sure things? Could Arizona assume most of the difference between Lee’s and Upton’s salaries and expect him to keep pitching at a high level into and through his mid-30s?

Both Lee and Upton are signed through 2015.

Lee Upton
2013 $25M $9.75M
2014 $25M $14.25M
2015 $25M $14.5M

Lee also has a 2016 club option for $27.5M and a $12.5M buyout. Upton has no such provision.

The salary difference is striking, and would almost certainly have to be addressed in some capacity. But, assuming the entirety – or even the vast majority – of the difference is not accounted for, this could free the Phillies up to use the newly freed money to address another pressing need in CF or 3B. Or, to a lesser extent, a depth starter.

The Phillies’s new top of the lineup could look something like this:

SS Jimmy Rollins
RF Justin Upton
2B Chase Utley
1B Ryan Howard
C Carlos Ruiz

With other positions remaining to be addressed. The rotation, then, would be left as:

Cole Hamels
Roy Halladay
Vance Worley
Kyle Kendrick
Tyler Cloyd

It’s significantly worse without Lee. Yet the lineup has a great shot at being significantly better, with a payroll ultimately lower than it was before (prior to finishing moves). Is it worth it? The rumor may be dead for now, but it’s still one worth keeping an eye on.