As we head into the last two months of the season, it's becoming pretty clear which teams are willing to buy and which are willing to sell; the teams that believe they're "in it" then have to decide whether or not to make a big push at the trade deadline. The Rangers, who now have the fourth best record in baseball, decided to make a splash earlier this month when they acquired Cliff Lee, and that trade has undoubtedly paid huge dividends so far. The Angels, who are now hovering around .500 and are 8 1/2 games out of a playoff spot, were also aggressive, trading for Dan Haren last weekend. The Red Sox are five games behind the Rays for the wildcard lead in the AL and would seem like the type of team that would be big-time buyers at the trading deadline, but it's also important to remember that they now have Victor Martinez, Josh Beckett, and Mike Cameron back on the team; all three missed many weeks during the season. The team could also have Dustin Pedroia back at second base within a month. Basically, the point is that they may have enough players returning from injury that they don't feel they need to make a big move at the trading deadline. The Yankees are currently in first place and have the best record in the majors. Depending on how long Andy Pettitte's groin injury sidelines him for, the team may be looking at another starting pitcher. With Lee and Haren off the market, it's realistic to figure that they would go after someone like Ted Lilly or Jake Westbrook.
What the Red Sox and Yankees seem most interested in is relief help; the Red Sox have a bullpen ERA/FIP/xFIP triple slash line of 4.45/4.81/4.68, and the Yankees' is 4.03/4.06/4.20. For the Sox, Hideki Okajima in particular has been a disappointment; his combination of increased walks (4.06 BB/9, a career high), decreased strikeouts (6.97 K/9, a career low), and an inability to get big outs (-1.18 WPA) has helped make him a below replacement level reliever so far. As for the Yankees, Damaso Marte's shoulder injury and Joba Chamberlain's habit of giving up a lot of hits have made them investigate the market for bullpen pitchers. The player that both teams are very interested in is Scott Downs. As of Sunday, they were considered by Fox Sports to be the front-runners in acquiring Downs. However, trading for him will certainly be difficult for both teams, as Blue Jays GM Alex Anthopoulos has demaded a very strong return package. From the Red Sox, Anthopoulos said that he would trade Downs for no less than either Casey Kelly or Jose Iglesias, who are both currently in Double A (click on the links for minor league stats from Baseball-Reference). As for the Yankees, the Blue Jays seemed to be in fierce pursuit of Chamberlain, and have reportedly given the Yankees the option of substituting Jesus Montero in the deal.
Personally, I have a hard time imagining either team saying yes to the Blue Jays. Kelly and Igleias are considered two of Boston's top prospects, and Montero is viewed the same way in New York. Chamberlain is obviously having his share of struggles this year, but the Yankees seem unwilling to part with a 24 year old who can throw in the upper 90s. Scott Downs is an excellent reliever: he has both strikeout and groundball tendencies while keeping walks to a minimum (he's posted an xFIP under 4 in all of his five previous seasons with the Blue Jays). But combine his age of 34 and his free agency at the end of the season with the fact that relievers are less valuable than starters, and you get a mismatch in terms of what the buyers and sellers want.
Stats are from Fangraphs and Baseball-Reference.