Charles Krupa/AP
By Jay Jaffe
July 29, 2014

Given the Rays' surge back into the playoff picture, Red Sox lefty Jon Lester has taken over the trade market's center stage from David Price. A key component of Boston's 2007 and 2013 championship run, the 30-year-old southpaw is a pending free agent, and the Sox (48-58, 1.0 percent playoff odds) are dead and buried in both the division and Wild Card races. With the two sides far apart in contract extension talks, the question as to whether the Red Sox will deal Lester — and if so, what they can get in return for a two-month rental — looms large.

Trade rumors: Red Sox listening on Lackey, Dodgers moving Kemp?

While the rest of Boston's rotation aside from John Lackey has crumbled around him, Lester has been at the top of his game this season. Despite lousy support from the defense behind him via a .312 batting average on balls in play, his 6.8 innings per start, 76-percent quality start rate, 4.7 strikeout-to-walk ratio, 2.62 FIP, 2.52 ERA and 155 ERA+ are all career bests, and his strikeout rate — 9.4 per nine or 25.7 percent of all hitters faced — is near his high. His performance has made clear that his dismal 2012 (4.82 ERA, 0.7 Wins Above Replacement) was an aberration, and he's actually outpitched Price in terms of run prevention (2.96 FIP, 3.08 ERA, 122 ERA+) and value (3.0 WAR to 2.7).

Keeping the homegrown Lester — who has put up a 3.64 ERA and 120 ERA+ through his nine seasons — would seem to be a no-brainer given his performance and popularity, but the Red Sox haven't been willing to offer him an extension in line with the going rate. They reportedly offered him a four-year, $70 million deal during the past offseason, and while they're said to have increased that somewhat, they probably have to get to at least five years and $100 million to have a chance, even if Lester is willing to take a hometown discount.

The two sides have broken off talks until after the season, and while Lester has said he's willing to return via free agency if he’s traded, dealing him would mean the Sox lose their exclusive negotiation period with him (the first five days after the World Series) and the right to make him a qualifying offer. The loss of a compensatory draft pick wouldn't matter to the Sox given the potential haul in prospects, but under such circumstances, other suitors wouldn't have to surrender their first-round pick either, likely broadening his market.

What follows here is a quick look at eight potential buyers connected to him in recent days, and what Boston's top trade targets within those organizations might be, given that they're reportedly asking for one elite prospect and at least one lesser one; note that I’m providing a thumbnail sketch, not trying to craft the perfect deal. The teams are listed alphabetically.


Having already traded their top two prospects in the Jeff Samardzija/Jason Hammel blockbuster, the A's wouldn't appear to have enough to acquire Lester, but that didn't stop them from reaching out. Oakland's top remaining prospect is 2012 supplemental first-round pick Daniel Robertston, a 20-year-old shortstop who's currently batting .296/.398/.465 at High-A, but he's said to be untouchable, and third baseman Renato Nunez (a 20-year old hitting .284/.345/.553 with 25 homers at High-A) probably has less appeal to an organization with such a glut of hot corner candidates as Boston. Club-controlled lefty Drew Pomeranz, the fifth pick of the 2010 draft and a player who won't be eligible for arbitration until after the 2016 season, could figure in such a deal, but Oakland has to be considered longshots in this race.

Blue Jays

According to CSNNE's Sean McAdam, the Jays have been the most aggressive of the latest wave of teams in pursuit of Lester. That would seem to hint that a power arm such as Marcus Stroman or Aaron Sanchez — both currently pitching for Toronto, the former in the rotation, the latter out of the bullpen — could headline the deal. Stroman has put up a 3.21 ERA while striking out 7.9 per nine thus far, though it's doubtful the Jays would give him up, given that he's a key figure in their contending bid. Sanchez, who outranked him on Baseball America's preseason list (32nd versus 55th) before battling control problems this year, might be easier to part with.

A pair of 21-year-olds who have split their seasons between High-A and Double-A, lefty Daniel Norris and centerfielder Dalton Pompey, could also figure into the mix. Norris, 25th on BA's Midseason Top 50 Prospects list, has three plus-pitches and has whiffed 11.0 per nine this year, while Pompey, 47th on that list, has hit .310/.390/.465 with 35 steals.


The Braves have shown significant interest in lefty reliever Andrew Miller, but via McAdam, they're said to have asked about Lester as well. With no prospect in the BA or Baseball Prospectus midseason top-50 lists, they may not have an elite prospect who would trigger a deal. Jose Pereza ranked 39th on the midseason list of ESPN's Keith Law; he’s a 22-year-old middle infielder who has hit .349/.375/.455 split between High-A and Double-A. Shifted from shortstop to second base this season because he was blocked by Andrelton Simmons, he’s an outstanding defender who would figure to move back to short with Dustin Pedroia ahead of him at second. Righty Lucas Sims, a 20-year-old who placed 40th on the preseason lists of ESPN and BP, is seen as a future No. 2 starter, but his strikeout rate has plummeted with a move to High-A.


Milwaukee's farm system isn't strong, but according to CBS Sports' Jon Heyman, general manager Doug Melvin hasn't been afraid to ask about Price or Lester. A trade for either would almost certainly center around 6-foot-6 righty Jimmy Nelson, a 2010 second-round pick who posted a 1.46 ERA and 9.2 strikeouts per nine at Triple-A Nashville before being recalled by the Brewers; he's got a 4.30 ERA and 22 strikeouts in 23 innings over four starts thus far. Ranked 38th on BA's midseason list, he's considered to be a future No. 2 starter. Alas, none of the team's other top prospects — centerfielder Tyrone Taylor, shortstop Orlando Arcia (brother of Twins outfielder Oswaldo) and catcher Clint Coulter — have climbed above High-A or are as highly regarded.


Via the New York Post's Joel Sherman and ESPN's Jim Bowden, the Cardinals are in the hunt for Lester as well. They're almost certainly not going to trade top prospect Oscar Taveras for a two-month rental, but the team does have a deep system and a crowded big league roster that could give them the edge in such a deal.

Triple-A outfielders Randall Grichuk and Steven Piscotty are nearly ready, while major league pitchers Shelby Miller and Carlos Martinez are under club control through 2018 and 2019, respectively. Grichuk, 22, was a 2009 first-round pick by the Angels who has been up and down with the Cardinals this year; he's hit .269/.320/.514 with 20 homers while playing all three outfield positions at Memphis, while Piscotty, 23, is a 2012 supplemental first-round pick currently hitting .293/.355/.412 as Memphis' regular rightfielder. As Sherman points out, also potentially in play is the Cardinals' Competitive Balance Round A pick, which can be dealt.


On Sunday, a club source told ESPN Boston's Gordon Edes that the Sox were considering a trade with the Dodgers involving Lester and Matt Kemp, but such a deal makes little sense given the outfielder's declining performance on both sides of the ball, the $107 million still owed on his contract, and his vocal disgruntlement; few players seem less tailor-made for the Boston fishbowl. Almost certainly, the only way such a deal would get done would be if the Dodgers also include one of their top two prospects, centerfielder Joc Pederson or shortstop Corey Seager.

The 22-year-old Pederson ranked 18th on BA’s midseason list and is currently tearing up the Pacific Coast League (.318/.450/.585 at hitter-friendly Albuquerque), but maturity issues and a 27.0 percent strikeout rate suggest he's not yet a finished product. Seager, the younger brother of Mariners third baseman Kyle, is a 20-year-old shortstop who ranked 16th on BA's midseason list; he's batting a searing .352/.411/.633 at hitter-friendly Rancho Cucamonga of the High-A California League. The Dodgers appear bent on keeping both, so unless they're willing to move 17-year-old lefty phenom Julio Urias (13th on BA's list), a deal for Lester appears unlikely.


Given a rotation fronted by Felix Hernandez and Hisashi Iwakuma and an offense that ranks dead last in the league in scoring at 3.84 runs per game, bats would appear to trump arms on the Mariners' shopping list, but they've been connected to Price and Lester nonetheless. The problem for them is that shoulder woes have dented the values of top pitching prospects Taijuan Walker and James Paxton; the former, 11th on BA's preseason list, missed seven weeks due to bursitis and has walked 13 in 15 innings over three major league starts since returning, while the latter, 99th on BA's preseason list, missed eight weeks due to a lat strain and is still rehabbing his way back. D.J. Peterson, who placed 46th on BA's midseason list, could be a target; a third baseman likely bound for first base or leftfield long-term, he has hit .318/.375/.586 with 23 homers at High-A and Double-A.


It would be a surprise to see Lester dealt within the AL East; the Boston Globe's Pete Abraham has reported that the Sox won't consider dealing Lester to the Yankees, but it's not known whether that prohibition extends to Baltimore. Via Fox Sports, the O's are known to have inquired; if Kevin Gausman isn't an option to be dealt, their package would likely center around either Dylan Bundy or Hunter Harvey.

The 21-year-old Bundy, the fourth pick of the 2011 draft, ranked second on BA's 2013 preseason list but didn't pitch due to elbow problems that culminated in June Tommy John surgery; he's made seven rehab starts and his stuff is starting to return. The 19-year-old Harvey, the team's first-round pick in 2013, has put up a 3.18 ERA with 10.9 strikeouts per nine in the A-level South Atlantic League, propelling him to 31st on BA's midseason list (Bundy was 10th there). Another pitcher likely to figure into such a deal would be 21-year-old lefty Eduardo Rodriguez, who's scuffled a bit at Double-A (4.79 ERA) but is young for the level and profiles as a mid-rotation starter.


Via Twitter, the Boston Globe's Nick Cafardo reported that "a couple of baseball executives think the Pirates may get into" the Lester talks, but that's about as much heat has been generated on this front. Even with Gregory Polanco now in the majors and Jameson Taillon missing the year due to Tommy John surgery, the team did place four players besides the latter on BA's midseason list: Righty Tyler Glasnow (21st), rightfielder Josh Bell (35th), righty Nick Kingham (37th) and outfielder Austin Meadows (47th).

The overpowering, 6-7 Glasgow has posted a 1.74 ERA with 10.8 strikeouts per nine at High-A Bradenton, though the 20-year-old righty needs to improve his ability to repeat his delivery. The 21-year-old Bell, a switch-hitter with a mature approach at the plate and a strong arm in the field, hit .335/.384/.502 at Bradenton before being promoted to Double-A Altoona, where he's still adapting. Kingham, a 6-5, 22-year-old, is nearly ready, posting a 3.08 ERA at Double-A and Triple-A; he could be up later this year. Meadows, the No. 9 pick of last year's draft, is a 19-year-old centerfielder with five-tool potential, but he's played in just 20 games this year after missing three months due to hamstring woes.

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