Bostong Red Sox: Trade-Deadline Possibilities

The Red Sox, year in and year out, have their name surfaced around the trade deadline and the weeks prior. The team is in contention annually, and they have the necessary payroll to make any type of deal without worrying too much about cost.

Boston often looks to upgrade with the ultimate goal of a world championship, along with possessing top prospects that teams covet.

The upgrade most Red Sox fans are eyeing is middle relief; a problem even more glaring than last season when Epstein felt it was necessary to trade for Eric Gagne. Manny Delcarmen is emerging quickly, but can he be trusted with Okajima falling so drastically from his elite set-up-man status?

Other than the bullpen, the obvious question for any contender is: can we upgrade the starting rotation?

Many names are being floated—Bronson Arroyo, Derek Lowe, Randy Wolf, Paul Byrd, Gil Meche, A.J. Burnett, Roy Oswalt—but in my mind, only two names really stick out as guys who can make an impact for a contender looking to win a title: Erik Bedard and C.C. Sabathia.

In order to acquire either one, a team needs A) motivation and B) prospects. A slim number of teams have both; the Red Sox are one and the Brewers could be the other. The Phillies, Cubs, and certainly the White Sox are questionable in terms of prospects.

Do the Red Sox need to deal for a starter? Not in any desperate way, but it wouldn’t hurt. Is it worth dealing a package of say, Michael Bowden, Josh Reddick, and Oscar Tejeda for three months of C.C. Sabathia, with the possibility of a costly extension or Erik Bedard for a year-and-a-half?

I would argue that Theo Epstein would be making a grave mistake if he pulled the trigger on either one of those. Any team is going to demand Bowden; he’s shooting up on prospect rankings with his performance in AA Portland as a 21-year old and is a future No. 2. It would be wise to hold off on trading him with a package for either Sabathia or Bedard, but it would probably be necessary.

Exhibit A: Erik Bedard. As we all know, Bedard was dealt by the rebuilding Orioles to the up-and-coming Mariners this winter. It turns out that the teams have switched roles; the Orioles turned out to be the winners with closer George Sherrill and CF-of-the-future Adam Jones, and the Mariners, weeks after firing their GM and coaching staff, are looking to deal Bedard.

I’m not convinced Adam Jones is going to become a star, but that trade has to be considered one of the worst of the last decade.

Bedard is a risky proposition for any contender. He’s very injury prone, having already aggravated his hip and back at some point this season. Bedard performed at the highest level of his career in 2007 with the Orioles (near Cy-Young level if he hadn’t been hurt) and is now falling back down to earth.

His ERA in 2008 is 3.97, compared to his career mark of 3.84. His K/9 last year hit 10.93, and it has now fallen to 8.06. He’s surrendered eight home runs while pitching in pitcher-friendly Safeco Field, and his FB rate is up.

Still, he has to be considered a coup for any contender—his 3.97 ERA, 1.32 WHIP, and 63 K in 70 IP is solid. He does come with a few red flags, mentioned very candidly in this News Tribune article.

I’m not the biggest proponent of team chemistry being vital for a team to win, but Bedard certainly seems like a prima donna with a long injury history. How would he fare in a rough-and-tough environment like Boston? Can he stay healthy for the stretch run? Are the declining statistics just a small sample size, or did Bedard experience his peak in 2007?

Too many question marks for me. I wouldn’t dare deal Bowden, Anderson (who should be untouchable), Reddick, Bard, Tejeda, or any big-time package for Bedard.

The other option is C.C. Sabathia, who has just begun pitching like the reigning Cy Young award winner. He started off 2008 in nightmarish fashion: 7.76 ERA, 34 hits in 26 innings, and 4 HR in April. Like any small sample for a good player, Sabathia has recovered to a tune of a 2.44 ERA in May and 2.40 in June.

Now that the Indians look destined for mediocrity, Sabathia’s name has been mentioned more than any other on the trade market. The Yankees have to be interested, as are the Phillies and Cubs. The Red Sox have also been uttered as a possibility.

The large caveat with Sabathia is that he’s a free agent at the end of the year, and surely he’ll demand a contract somewhere near the deal that Johan Santana got with the Mets. The problem with Sabathia is that he’s a much riskier bet than Santana, due to his stature and shorter track record.

In order for Theo to make a deal for C.C, he’d likely demand a timeframe to negotiate a contract extension. If Indians GM Mark Shapiro declines, I find it very unlikely Epstein trades his top prospects for three months of Sabathia.

Unless more names begin to emerge, the Red Sox may be better off holding on to their prospects and payroll flexibility, and going to battle with the current rotation. Beckett is an October dynamo and a bona fide ace when the chips are down. Even if the rest of the rotation is questionable, Dice-K and Lester for Games Two and Three is nothing to get worried about.

I’d even go to war with Bartolo Colon in Game Four. I would advise the front office to keep the idea of dealing for Bedard or Sabathia on the table for a tremendous offer, but instead, look towards help in the bullpen (hello Huston Street?).