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With the major-league trading deadline right around the corner, it is safe to say that we are going to soon find ourselves immersed in rumor after rumor, proposed trade after proposed trade, and we will love every single minute of it. Cliff Lee can no longer be had after the Rangers executed what felt like the baseball equivalent of a last-second eBay sniping, but there are still a bevy of potential playoff contenders with starting pitching improvements on their radar. Even though Lee is off of the table, these teams can still bolster their starting staff, be it through impact toward the middle in the form of Ted Lilly, or the removal of waste at the back end by adding the likes of Jeremy Guthrie.

One name that remains rather interesting is Roy Oswalt, the beleaguered face of the Astros, who has seemingly reminded everyone listening each and every week that he would waive his no-trade clause to join a team that matters either now or into the future. I half-expect to wake up each morning to find out that Oswalt is now willing to accept a trade to Japan, the independent leagues, or whatever softball team Eric Byrnes currently rakes for, just to get out of the miserable situation in Houston. But will he actually be traded this year?

He needs to be traded this year, to really help his current employer, but it is a wonky situation for sure. The Astros are in dire straits as far as their farm system goes, and they lack impact talent at the major-league level capable of netting minor-league depth in a fire sale. In other words, they don’t even have what it takes to start the rebuilding phase they needed to start four years ago. In Oswalt they have an asset that could conceivably extract a good amount of talent from an acquiring team in return, but a huge roadblock apparently exists in the mind of owner Drayton McLane, who still values the righty as if this was the 2005 season.

Contractually, Oswalt will make $15 million this year and $16 million next, with a club option worth $16 million for the 2012 campaign that comes attached to a $2 million buyout. Given that the season is past the halfway point at its current juncture, an acquiring team could be responsible for $24-25 million, given the remainder of his 2010 salary, the entirety of what he is owed in 2011, and the buyout prior to the 2012 season. If it decides to hold onto Oswalt, we are talking about a potential $40 million commitment over the next 2 1/2 seasons. On top of that, because of the situation in which the Astros currently find themselves, you can see how they'd expect a good amount of minor-league talent to be sent their way to make the trade worthwhile.

Put yourselves in the shoes of one of the contending teams looking to improve their rotation. Do you really think it prudent to absorb that hefty a financial commitment for Oswalt and part with potential major-league talent of the future? It seems to me to be one of those one-or-the-other type of trades, where the acquiring team either gives up plenty of talent while the Astros pay a decent portion of Oswalt’s salary, or the acquiring team takes on all of the remaining salary but does not part ways with much in the talent department. I would find it very hard to believe that too many teams are going to line up to trade away their talent and pay that salary.

McLane could help matters by kicking in enough of Oswalt’s salary to entice a return more commensurate with how he values Oswalt, but he has previously alluded to the idea that such kick-ins went against his grain. Perhaps the dire nature of the situation has helped to change his mind recently, because the Astros are not going to improve themselves without a very good return, which will not be achieved if a team has to pay Oswalt’s entire remaining salary. One thing to keep in mind is that Oswalt is still a very good pitcher, and if his first-half resurgence is any indication, he could certainly have an impact on the playoff picture down the stretch.

But here is where the situation gets even more interesting: the teams that could utilize his services the most do not necessarily have what it would or should take to pry Oswalt away. To that end, I tried to identify several teams who might be in the hunt, in order to propose some potential trades. This way, we can more readily visualize what could be heading the Astros' way as opposed to the blanket suggestion that they trade the pitcher for prospects. The teams that could use another front-of-the-rotation pitcher but could also conceivably make a move are the White Sox, Twins, Mets, and Red Sox. Resisting middle-relief jokes, with who would these teams have to part with to get Ed Wade to pull the trigger? Assume that the Astros would add $8-10 million to the deal.

White Sox trade Dayan Viciedo, Brent Morel, and David Holmberg: Ken Williams might be the most creative general manager in the league, what with his absorption of Alex Rios’ contract for nothing tangible in return, or with the blockbuster deal involving Jake Peavy that seemingly came out of nowhere. A month ago the White Sox would not even have been mentioned in the same breath as a trade to sure up a potential playoff rotation, but after going 26-5 in their last 31 games the Sox are atop the AL Central. They may have been playing over their heads, but an acquisition of Oswalt could serve as a counteractive measure against regression.

Viciedo would be the centerpiece of this deal from the Astros' point of view. The Cuban defector had a mediocre rookie season in Double-A last season, but a .290/.329/.525 showing at Triple-A Charlotte this season proved worthy of a major-league call-up toward the end of June. Since entering The Show, he isn’t lighting the world on fire, but he has become a regular in the lineup at the hot corner. Realistically, he isn’t good enough in the field to man the position, and likely has a shift to first base in his future. At just 21 years old, he could blossom into a very nice hitter, and while he won’t make Astros fans forget Jeff Bagwell, he could certainly make them forget that they actually used Pedro Feliz at the position for part of the season. This deal would be contingent upon the Sox re-signing Paul Konerko; if the veteran departs, Viciedo would make a ready replacement.

In Morel the Astros would get a third baseman who can play the position in case the Chris Johnson experiment fails. He is a good hitter with gap power who gets good marks for his makeup. He won’t make a huge impact in the major leagues, but he is still a worthwhile piece, as he has very few weaknesses, even if his strengths aren’t that strong. Holmberg was drafted in the second round last year out of high school and what the lefty hurler lacks in pure stuff he is known to make up with in polish. He has a plus curveball and consistently hits the low 90s with his heater. His rookie league numbers over the last two seasons have not been insanely impressive, but the potential is there.

Mets trade Fernando Martinez, Kirk Nieuwenhuis, and Reese Havens: Martinez is one of those prospects given a free pass due to several caveats, such as consistently being three or four years younger than his competition or suffering from injuries, but as our comment in the most recent annual suggests, at some point, the guy has to start hitting, excuses or not. He is still young enough to make an impact in the majors, but his .258/.320/.429 line pales in comparison to the .290/.337/.540 he displayed before suffering a knee injury last season. He is only 21 years old, so it would be premature to say he will never work out, but if the Mets are starting to sour on the speedy outfielder, it would behoove them to try and use his past reputation in an Oswalt deal.

Nieuwenhuis, appropriately nicknamed Captain Kirk, has good range in the outfield even if his future isn’t necessarily as a center fielder. Scouts say he has a big-league body, which is to say that when you look at him, he has the look of a major-league player. After a .282/.364/.479 showing at Hi-A St. Lucie and Double-A Binghamton last year, he has put up a .306/.348/.541 line in Binghamton this year. Add the hitting skills to the defensive chops, and you have an outfielder perhaps without the upside of Martinez, but with much less of the downside.

Havens entered the system as a shortstop but has since shifted to the keystone. That isn’t the only aspect of his game that has changed, as he has also altered his swing, leading to improved results. He is currently hitting .312/.386/.592 overall, with a .338/.400/.662 line since being promoted to Binghamton. Havens isn’t very fast and his defensive skills are nothing to write home about, but solid plate discipline in addition to the power at what is perceived to be a less powerful position earns him extra points.

Red Sox trade Lars Anderson, Ryan Kalish, and Drake Britton: While I immediately think of the character Lars from the film Heavyweights whenever I hear the name of the first prospect listed above, Anderson has fallen quite a bit since being labeled the Red Sox's top prospect entering the 2009 season. A back injury and perhaps nerves led to a sub-par second half, and while his .261/.354/.449 line represents an improvement from a year ago, it does not exactly scream big-league success. After all, when a first baseman hits like Lyle Overbay in Double-A, what can be expected in the majors? He wasn’t touted so highly for no reason, however, and would be a worthwhile acquisition for the talent-sapped Astros.

In Britton the Astros would be taking on risk with upside, as he is a southpaw currently rehabbing, but who can dial it up to 96 mph on the radar gun. Kalish is a much more polished player, and after hitting .302/.384/.561 in the second half of last season, he has split time at Double-A Portland and Triple-A Pawtucket this season, hitting a Willingham-like .307/.405/.502. A very solid base-stealer, Kalish could turn out to be a 20-20 player with more upside than Hunter Pence.

Twins trade Ben Revere, Joe Benson, and David Bromberg: It’s easy to suggest that the Twins could offer a package centered around Wilson Ramos to extract Oswalt, given that the Mauer-blocked catcher was reportedly the centerpiece of a purported Cliff Lee deal, but the one position at which the Astros have a decent prospect is behind the plate with Jason Castro. As the Rangers have shown recently, you can never have enough catching prospects, but the deal above would leave Ramos in the system while offering the Astros a variety of talent.

Revere is a very raw outfielder, with plenty of speed and range, the ability to hit to all fields, and plate discipline good enough to avoid strikeouts while sustaining a high on-base percentage. He hasn’t offered much in the power department lately, but at worst he could turn into a Michael Bourn clone when the current Astros center fielder becomes too expensive for what he brings to the table.

Benson is another center fielder with tools aplenty, but one who comes with question marks. The biggest question has been answered with his performance so far, as scouts were unsure of his power. Currently hitting .266/.354/.553 combined between time spent at Double-A New Britain and high-A Fort Myers, power has certainly been on display. Much as is the case with Martinez and Nieuwenhuis with the Mets, one member of this duo has much more upside than the other, while the other member offers much less downside.

Bromberg, despite leading just about every league in which he has pitched in strikeouts, is another of the prototypical Twins pitching prospects, someone armed with deception, solid off-speed offerings and pitching savvy to make up for a lack of pure stuff. Regardless, pitchers don’t consistently miss bats without reason and, again, to a system devoid of talent, even a pitcher that projects as a third or fourth starter is appetizing.

Where Will He Go?
Which of the above deals would make you pull the trigger? Are there other teams or players that could be included?

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crperry13
7/16
None of those deals excite me (an Astros fan), mostly because outfield is the one position in the minors that the Astros aren't bleeding. They have no great OF prospects certainly, but with Bogusevic waiting his turn, Jay Austin, J.D. Martinez, and a couple others performing well enough to exceed Carlos Lee's current production, the Astros would be better served with infield and pitching. That said, I would lean towards the White Sox deal, with the added incentive of Oswalt pitching with his hunting buddy Peavy next season.

One possibility I haven't heard mentioned: Obtaining a package from the Angels starting with Brandon Wood? Wood showed too much potential in the minors, but the Angels seem to be done with him. A position change might have negatively affected him, and he could be a change-of-scenery, change-of-coaching-voice kind of guy. For one, I would love to see Wood given a shot at shortstop with the Astros, with Jeff Bagwell as a hitting mentor. That's the type of gamble the Astros need to take, buying major-league ready players on the cheap, and restocking the very lower levels of the minors. The Angels could do that with little loss to their current situation, and they definitely could use Oswalt.
flalaw
7/16
I think we can cross Boston off the list. Acquiring Oswalt would trigger the luxury tax for the Red Sox, meaning there would be a 30% premium on top of what they'd have to pay Oswalt.
hennethannun
7/16
I don't think the red sox are likely to acquire Oswalt because of the length of his contract.

Having just signed Beckett and Lackey, the red sox now have Lester, Beckett, Lackey, Buchholz, Wakefield and Matsuzaka all under contract for at least the next 2 seasons (though wakefield's contract is at the team's discretion).

It wouldn't make much sense to invest another 25/40 million and at least 1.5 seasons in a seventh starting pitcher. Not unless they think they can get out from under Lackey or Beckett (or intend to Buchholz) this off-season.
TheBish
7/16
I think the Red Sox would love to get rid of Matsuzaka, who may find some success in the NL, should Brad Mills be willing to take on that headache. Would the Astros take him instead of throwing in cash?
russadams
7/16
Congratulations, Mr. Simms. You are the fattest boy in camp.
dantroy
7/16
Maybe I'm crazy, but if the Astros don't absorb some of the $, I think they get one good (B+) prospect and 1 or 2 meh guys, and that's it. E.g., using the NYM example, they get FMart but the other guys in the deal wouldn't be as as good. If they take on $, then some of the packages above look more realistic.
EJSeidman
7/16
Dan, I said in the article to assume the Astros kick in $8-10 mil to make these work.
dantroy
7/16
You did. My bad.
duanstokes
7/16
jaysus.
I don't think the mets are paying that much - I certainly hope not.
rjmoore
7/17
Agreed. I don't see much analysis in this piece frankly. It seems like the author just picked a few prospects from each team that might be interested. I'd have liked some explanation of how much these prospects are actually worth, maybe using Victor Wang-style analysis; how much exactly the Astros would have to chip in to make it fair; or even what prospects the Astros might be interested in, given their current farm system. The proposed Mets package is very outfielder heavy - is there a reason for that? Anyway, I've enjoyed Eric's work in the past and think he should revisit this subject.
thsaladboy
7/16
I think all the deals mentioned here look a bit ridiculous for a slightly overrated pitcher whose peripherals haven't looked this good since 2005, if ever.
crperry13
7/16
Back up your point, because that's a pretty weak statement without proof.
tbwhite
7/16
The notion that the man who traded Curt Schilling and Scott Rolen away in their primes for Omar Daal, Travis Lee, Vincente Padilla and Placido Polanco would be capable of getting the returns proposed here for Oswalt is ridiculous. Given Wade's track record another GM would be crazy to even offer him anything remotely close to fair value for Oswalt.

How about Oswalt to the Reds for Homer Bailey, Yonder Alonso and Micah Owings ? That sounds about right for Wade, a headcase, a guy more suspect than prospect, and a never-was.
hyprvypr
7/17
If I'm the reds, I'd turn that offer down by not replying. Who do people think Oswalt is? Cliff Lee?
tbwhite
7/17
I think your over-valuing those guys a bit. Bailey is hurt and has had almost no success in the majors. Alonso is a 23yo 1B is AAA with a .700 OPS, and Micah Owings is a good hitting pitcher. It's not that great a package. Two or three years ago maybe, but not today.
JoshC77
7/17
As a Reds fan, I'd be OK with that deal (or at least the general concept). Bailey strikes me very much as an Edinson Volquez (when he was still with the Rangers) type of pitcher, one with talent but one who needs a change of scenery. That said, I'd hate to see him blossom for a division rival. Now, if the Reds could somehow talk them into taking on Francisco Cordero's contract....even better.
Justice
7/16
For two reasons, I don't think the White Sox will get Oswalt. First, he doesn't seem to want to leave the NL and Ken Williams has recently voiced doubts about the effectiveness of NL pitchers who go to the AL. Second, the deal you propose would leave the Sox with very little in their farm system and would take away two players (Brent Morel and Dayan Viciedo) who could very well play third and first base, respectively, in 2011, even if the Sox do re-sign Paul Konerko. In that scenario, I could see Konerko and Viciedo splitting time at 1B, Viciedo occassionally spelling Morel at 3B and Konerko, Viciedo and others (Carlos Quentin, Juan Pierre, perhaps Andruw Jones) at DH.
hyprvypr
7/17
Why would any of those teams give up that amount of talent for a pitcher who's well past his prime and now only slightly above replacement level? I just don't see it, unless the Astros pay a huge portion of his salary.
JeffreyLyon
7/17
You do realize that Oswalt has a 3.34 SIERA, 11th in the majors for pitchers with over 60 IP, and a WARP of 4.3 at the moment, right? How is that "only slightly above replacement level"?
hyprvypr
7/17
Because his ERA over the last three years is a bit over 3.6. Maybe more accurate is 'slightly above average' pitcher. I just don't see him finishing with that low a SIERA, especially at his age.
mblthd
7/17
I think the Reds' GM busts a gut laughing at that offer.
Oleoay
7/18
Eh, the Pirates went through a rebuilding phase with an even more sparse major league and minor league roster... and they were able to get some talent back. I think the Astros have more pieces to move right now than the Pirates did when they started.

Also, I think a contender would be able to acquire Oswalt without making the Astros absorb much of his contract. It worked for Lee (twice) and Halladay and the prospects needed to acquire Lee and Halladay weren't too pricey.
antoine6
7/18
Wait, the Pirates are the model of rebuilding successfully?

They still don't have enough young talent to be able to compete successfully in the near future, and their two best young players (McCutcheon and Alvarez) were drafted, not acquired through trades. They haven't gotten anything back worth rebuilding around in any of their trades.
Oleoay
7/18
We can't measure whether the Pirates have been completely successful yet or not. But the Pirates seem to be at a better state at their major and minor league level then they were a year and a half ago.

My point is that the Astros have more quality players to trade/rebuild with than the Pirates did. The Pirates major and minor league system was almost completely barren... at the major league level, they had Jason Bay and a bunch of scrubs. The Astros have Oswalt, Berkman, and some other parts they can move. All they need to do is show some initiative by either by trading off veterans, refusing to sign free agents that would cost them draft picks and/or using those picks to draft smartly.
jake726
7/18
I wouldn't trade Kalish or Lars straight up for Oswalt, especially Kalish. Either player is superior to the package given up for Victor Martinez last year. And, Victor Martinez is a similarly valuable player to Oswalt, with a much cheaper contract who filled a very real need for the Red Sox. Oswalt is expensive, was on a steady 5-year decline going into this season, and starting pitching is about the furthest thing from a need for the Red Sox once another week passes and Beckett and Buchholz are back.