Pirates Emerging as Dark Horse for Red Sox Ace Jon Lester

Jul 25, 2014; St. Petersburg, FL, USA; Boston Red Sox starting pitcher

Jon Lester

(31) throws a pitch during the second inning against the Tampa Bay Rays at Tropicana Field. Mandatory Credit: Kim Klement-USA TODAY Sports

Out of the haze that annually surrounds sweepstakes for premier players at the trade deadline, the Pittsburgh Pirates are emerging as a dark horse to acquire Red Sox right-hander Jon Lester, Jeff Passan and Tim Brown of Yahoo Sports report. 

If this is indeed the case, then the Pittsburgh would appear to become the immediate favorites to land Boston’s ace. For all the talk of Corey Seager, Julio Urias, Joc Pederson and all the high-end young talent that the Dodgers – the other organization most commonly linked to Lester, and his AL East competitor, David Price – the Pirates have more.

ESPN.com’s senior writer Keith Law recently ranked their farm system as the fifth best in the game. In right-handers Tyler Glasnow, Jameson Taillon and Nick Kingham, and outfielders Josh Bell and Austin Meadows,   the Pirates have five prospects listed in Baseball America’s mid-season top 50 rankings, four of which are near major league ready. They also have a pair of hitters – shortstop Alen Hanson and catcher Reese McGuire who ranked in the latter half of MLB.com’s recently updated top 100 list, coming in at  #80 and #81, respectively.

But as with every other team in these Lester negotiations, the Pirates appear bent on acquiring the free-agent-to-be without giving up their top young plays. As MLB.com’s Tom Singer writes, Pittsburgh is unwilling to include any of the top five prospects on BA’s list in a potential deal. Instead, they are attempting to structure a deal around Hanson and JaCoby Jones, a 2013 third round pick who is enjoying a strong season in the Class-A South Atlantic League – .834 OPS, 16 home runs – but who, at 22, is a little old for the league. 25 year old Major League Outfielder Jose Tabata, a former Baseball America top 100 who has fallen out of favor in Pittsburgh, is reportedly a “wild card” in trade talks.

Considering Hanson’s proximity to the majors and Boston’s uncertainty over the future at shortstop, that might be enough to swing a deal. It doesn’t come close to crowning them outright front-runners, though.

If the Dodgers acquiesced on just one of their top three prospects, they would have a better offer on the table than Pittsburgh. And the same almost definitely holds true for if the Mariners offered starter Taijuan Walker, if the Orioles relented on one member of their age 23 and under pitching trio of Kevin Gausman, Dylan Bundy or Hunter Harvey, or if the Cardinals included outfielder Oscar Taveras.

None of those teams have shown any inclination to do so, however, and this may come down to whichever organization balks first. If no team does – and with little over 24 hours left before the deadline, its looking increasingly like they won’t – then Hanson, Jones, and Tabata could the best proposal Boston receives. Or Pittsburgh could be the team that balks.

The Pirates do have at least one sign in their favor.

Singer also wrote in his piece that Pittsburgh informed Boston of their own deadline for a deal: 7 PM ET, just before Lester made his scheduled start at Fenway Park. Several hours later, the Red Sox announced that Lester had been scratched from that start. Its possible that other teams made the same demand as the Pirates, but they are the only ones known for sure, and this just extended their negotiating window by nearly a full day.