Is It Time To Trade Oswalt?

added 8/28/2009 by Bob Hulsey

For most of the decade, Roy Oswalt has been the one constant on the Houston pitching staff. You could pencil him in for 15-20 wins every year and know he'd give you his best effort every time out on the mound. But it may be time to send him packing, not during the season but during the winter months.

Let me start by saying that, the Astros have many reasons to thank the young hurler from Wier, MS. Without him, the Astros would not have reached two LCS's and one World Series. He's been a stand-up guy and a fierce competitor. If the Astros looked like a team able to contend in the next few years, I'd want to keep him around.

But the reality is that the Astros are going to need to take a step or two backwards before they can go forward. Since 2007, they have tried to milk another title by putting older and older teams on the field and it clearly hasn't paid off.

Going into next season, the Astros will have to pay three big salaries, all with no-trade clauses. Two of them, Lance Berkman and Carlos Lee, give no indication they would approve a trade. Oswalt dances around the subject but it seems clear he would go someplace that could put a World Series ring on his finger and fit in with his lifestyle.

It's been a frustrating year for Roy who is not used to being this deep into the season and still be stuck on seven wins. He's in danger of not reaching ten wins for the first time in his big league career. He hasn't been honored by much run support and, when he has, something has often kept him from getting the win, whether it be a minor injury, some errors behind him or a bullpen meltdown.

Oswalt is not a subtle man and, though he tries to say the right things, I think it is clear he is not fond of Manager Cecil Cooper and he doesn't like the direction the ballclub has taken. He lobbied hard to have his friend Jake Peavy brought in from San Diego when the Padres put him on the trading block last winter but Owner Drayton McLane reportedly told Oswalt he wouldn't do it unless Oswalt agreed to sacrifice some of his own salary to make the numbers work.

You don't have to read much between the lines when he says he "didn't come here to be on a mediocre team" and claimed, after his most recent loss in St. Louis, that the players are "just going through the motions" to know he's not happy playing here.

If the Astros are able to jettison his $15 million salary for 2010, it will give the team a lot more payroll flexibility than they now appear to have. If, for example, Randy Wolf were to sign with Houston for the same $8.3 million the Astros were ready to sign him for last winter before pulling the offer back, that would still leave Ed Wade an extra $6.7 million to fill other needs. No doubt, we would miss Roy's talent but an ace isn't that valuable when the rest of the team doesn't produce (ask the Blue Jays).

So, regretfully, it may be time to say goodbye to Roy while his trade value is still high and he still has some time left on his contract for a new club to enjoy. Since Oswalt has a no-trade clause, the trade partner would have to be one that can give Roy what he wants.

Reportedly, the Cardinals and Cubs are two teams on his short list but there's almost no chance the Astros will deal him within the division. The Braves are another team that might be a preferred destination. However, Atlanta has good starting pitching and a limited budget. It doesn't appear to be a good match.

So, where else could Oswalt go? I think Oswalt would prefer to be in the South or the Midwest. Teams like Arizona, Kansas City and Minnesota don't have the payroll to take Roy's contract. Likewise, Florida and Tampa Bay would be good fits except the teams don't have the money.

I see only two prospective matches that might be darkhorse winners in the derby to add Oswalt to their pitching staffs. One would be the Chicago White Sox. The Sox now have Peavy under contract but could they add Oswalt's $15 million as well? They'll be free of Jose Contreras' $10 million contract and Jim Thome's $13 million deal this winter plus the six million owed to former Astro Octavio Dotel. I think Oswalt would prefer to stay in the National League but his hunting buddy Peavy eventually relented and so could Roy.

What I'd like to see the Astros get back in return is lefthanded starter John Danks, a developing pitcher who will be under club control until 2012, then toss in one or two other prospects like AAA reliever John Link and AA 3B-OF Dayan Viciendo. The latter is a Cuban immigrant who was signed to a 4-year, $10 million dollar contract through 2012. His numbers haven't been great either on offense or defense during his first season in American baseball but the 20-year-old is facing older competition and could be a star in a few years. His 240-lb weight is a bit scary for a third baseman but he'll probably hit the bigs about the time that either Berkman or Lee is ready to move on.

There are a few other ways a deal could work although the Sox gave up some top prospects to get Peavy and would be hit hard again for any trade involving Oswalt.

The other possibility is the Philadelphia Phillies. There's an $8 million option on Cliff Lee which would seem to be a bargain, Brett Myers hits free agency and the Phils will also be almost done paying off a combined $15.58 million in bad money owed to Adam Eaton and Geoff Jenkins. I'm not sure what the Astros could get in return for Oswalt but Ed Wade certainly knows their farm system and there are some sons of past Astros who could generate a little splash. I could also see the Texas Rangers as an outside possibility if they can get their ownership issues behind them.

Until recently, the thought of dealing Oswalt would have been met with knee-jerk rejection but it seems clear Roy doesn't want to stay through a rebuilding run (if there is one) and he won't be happy about being an Astro if Cooper is still the manager. Dealing away his salary brings relief and flexibility to Houston's payroll which might make them a little more daring to offer arbitration to players who will bring draft choices our way if they sign elsewhere.

Oswalt watched Billy Wagner get increasingly mouthy in 2003 about McLane not being willing to spend for a winner. It eventually forced a trade that coincidentally freed up salary for Houston to bring in Andy Pettitte and Roger Clemens. I don't think Oswalt wants to leave town the same way, but every week he seems to get a little bolder in saying the same things Wagner did and, perhaps, will get a similar result.

There's some talk that Oswalt is simply trying to be a team leader and fire up his teammates. I think he'd prefer McLane simply spend more money to make the Astros a winner. It doesn't seem to fit a likely downsizing the Astros will do next year, given the economy and the drop in attendance. I think it would be better for Roy's competitive nature if he isn't around to watch the rebuilding and, instead, concentrates his last few years on being a champion somewhere else.

In agreeing to go, he also helps the Astros get serious about starting fresh with a new generation of stars instead of trying to wring one more season out of some dying careers. It seems odd to say it, but trading Roy could be the best thing for both parties.