Will Roy Be Leaving?

added 5/31/2009 by Bob Hulsey

Most Astro fans would consider it unthinkable that pitcher Roy Oswalt, third on the franchise’s all-time wins list, might wind up this season pitching for another ballclub and, while I think the possibility is still less than 50%, there are gathering signs that it might just happen.

Entering Monday’s start against Colorado, Oswalt has been underwhelming as the team’s ace. His 1-2 record and 4.62 ERA are unlike an ace as much as they are unlike Oswalt who has been perhaps the most steady pitcher of this decade (130-66, 3.18 ERA for his career).

It should be comforting to know Oswalt typically is a better pitcher in the second half of the season but will he do that in 2009 for the Astros or somebody else? Oswalt has a no-trade clause in his contract, so the ultimate answer to the question will be his.

Oswalt is unhappy with owner Drayton McLane who won’t push to acquire San Diego ace Jake Peavy, a personal friend of Roy’s. Oswalt’s also not happy with Manager Cecil Cooper who appears to have ruffled some clubhouse feathers with his lineup and pitching decisions.

Some saw Cooper’s postgame replies after Oswalt’s game in Cincinnati last week as more evidence that the two men are at an impasse:

"We just need him to step up to be who he's supposed to be," a frustrated Cooper said after the 6-4 loss to the Reds, a game which saw Oswalt struggle to hold a 4-3 lead in the middle innings.

So is Oswalt on the trading block? The Phillies and the White Sox apparently think so. The ChiSox have had team special assistant Bill Scherrer following the Astros since they were spurned by Peavy who used his own no-trade clause to nix a deal to Chicago the Padres approved. For his part, Oswalt has let it be known that he, too, would not accept a deal to Chicago.

The defending World Champion Phillies are also in desperate need of starting pitching after Brett Myers opted for hip surgery that will keep him out 3-4 months and 46-year-old junkballer Jamie Moyer is off to a bad start.

I’m not sure either destination would meet Oswalt’s approval. The White Sox are led by Ozzie Guillen who is just as apt to rub Roy the wrong way as Cooper has. The Phillies play in a bandbox that frustrates even the best of pitchers. The Mississippian may feel out of his element in either location although he has former teammates in both cities.

The Phillies and White Sox, for different reasons, are both in "win now" mode – something the Astros always profess to be in yet they haven’t made a move that truly reflects that since Roger Clemens was signed in 2006. Both teams have good but not great farm systems and aggressive general managers.

Selling themselves to Oswalt may be difficult but there’s one way they could probably get his approval. They could acquire his friend, Peavy. Since both men have no-trade clauses, the only way that will likely work is to make a three-way trade with the Padres and the Astros so each is aware that the other is part of the deal.

How might this work? Let’s presume that the framework of the Padres-White Sox deal remained in place and the Astros accepted a deal that would send them lefthanded pitcher John Danks, righthanded pitcher Jose Contreras and outfield prospect John Shelby, Jr.

Danks is talented, still young (24), cheap and under club control. Contreras, the Cuban defector, carries a $10 million dollar contract and has been terrible this year. His presence in the trade is simply to make the money fit. His contract is up at the end of the year so he’d only be a liability this season. Shelby projects to play like his old man, the former Oriole and Dodger from the 1980s who hit for power and speed. He probably wouldn’t be a star but should be a productive big leaguer.

The Padres and Phillies have not had discussions about Peavy to my knowledge so it is hard to know what the Padres would require to unleash their star but let’s say a hypothetical agreement included pitcher Kyle Kendrick, catcher Lou Marson and outfielder John Mayberry, Jr. The Astros might then opt to receive for Oswalt lefty relief pitcher J.C. Romero and pitching prospects Antonio Bastardo and Kyle Drabek.

Romero would provide immediate bullpen help and some financial softener for the deal to go through. Bastardo is a lefthander who is dominating AA hitters in Reading while Drabek is the son of former Astro Doug Drabek who is projected to be a relief pitcher after going through Tommy John ligament surgery.

Any team thinking of pulling off a trade for both Oswalt and Peavy would be surrendering the potential fruits of their farm system and blowing out their payroll budget. But that’s what teams who feel they must "win now" are often tempted to do. For the Astros, the end game is to slash payroll and get younger while provide the best route to replenishing the farm and yet staying competitive.

It’s a sticky deal because you have to make five parties happy – the three teams and the two All-Star pitchers. Any one of them who doesn’t like the deal torpedoes the whole mission.

The Astros are very unlikely to send Oswalt to another team in the N.L. Central. The Padres are very unlikely to send Peavy to any rivals in the N.L. West. Neither Peavy or Oswalt are particularly fond of the American League. The Marlins and Nationals are too broke to make such a deal work. The Braves aren’t playing well enough to be thinking about this year. That leaves the Mets and Phillies, two destinations not high on the list of either pitcher.

That’s why it’s important for some contender to trade for them both or they likely won’t get either. The Astros won’t trade for Peavy. The Padres won’t trade for Oswalt. Both are in the middle of multi-year contracts. So the only way to lure one is to lure both and find a way to make the dollars work.

If they can accomplish that, the idea of a Buehrle-Oswalt-Peavy rotation for the ChiSox or a Hamels-Oswalt-Peavy rotation for the Phils should subdue some of the anxiety a little bit about taking on more debt than your local mortgage bank. It would make the team that has them instant favorites to win their division and make the postseason.

For both hurlers, part of the problem is that their current homes are getting less comfortable and, face it, nobody likes losing which is what both the Astros and Padres will spend this year doing.

Of course, the Astros might not be so bad if Oswalt steps up the way Cooper implores. But should there be irreconcilable differences between the ace and his manager, perhaps a change in scenery will serve all parties well.