We've heard about negotiations between Lester and the Red Sox—or perhaps the lack thereof—for months now. With each passing week that Lester remained unsigned for 2015—and with each additional loss suffered by the Sox—this scenario became more and more likely.
But it's still hard to believe that the Red Sox seem not only willing to, but rather insistent on trading their homegrown ace at the deadline, as they look to capitalize on a seller's market.
Those rumors have only intensified in the last few hours, as late Tuesday night Lester was scratched from his scheduled start against the Toronto Blue Jays tonight. Brandon Workman will start in his stead, and while there's no deal in place yet for Lester, the writing is on the wall: Lester has likely thrown his last pitch for the Red Sox in 2014, and there's a chance he's thrown his last pitch for the Red Sox ever.
When a pitcher of Lester's caliber is made available, most teams in the game will have some interest. But according to ESPNBoston's Gordon Edes, six teams remained in the hunt for Lester as of Tuesday night:
Six teams still in on Lester, according to source with direct knowledge: Dodgers, Cardinals, Pirates, Blue Jays, Orioles, Athletics— Gordon Edes (@GordonEdes) July 30, 2014
While Edes lists those teams as contenders, as is the nature with trade rumors, we've seen conflicting reports about whose interest is sincere. FoxSports.com's Ken Rosenthal tweeted that the Milwaukee Brewers were out on Lester on Tuesday night, and WEEI.com's Rob Bradford tweeted that the Baltimore Orioles and Toronto Blue Jays were largely out of the running, too.
Those teams could resurface with new offers in the coming hours, to be sure, but for now let's focus on the four teams no one's ruled out yet: the Pittsburgh Pirates, the St. Louis Cardinals, the Los Angeles Dodgers and the Oakland Athletics.
As Yahoo Sports' Jeff Passan and Tim Brown wrote on Tuesday, the Pirates have emerged as a "dark-horse" candidate to land Lester, and they have the type of young talent the Red Sox would likely be looking for in return for their ace. Outfield prospect Josh Bell has been a popular name bandied about as the central piece in a Lester deal, though Edes cautioned that Bell may not necessarily be involved.
But with or without Bell, the Pirates would seem to have the motive and the assets to acquire Lester, and the southpaw could make the difference in a tight NL Central race.
The Cardinals know that too, of course, and as ESPN.com's Buster Olney tweeted out Wednesday morning, that could be a big part of the reason they've maintained interest in the Lester sweepstakes:
At this point, the interest of Jon Lester from Cardinals, Pirates and Brewers is almost as much about keeping him from rivals as adding him.— Buster Olney (@Buster_ESPN) July 30, 2014
St. Louis is stacked with young outfield and starting pitching talent in the majors and upper minors, and so is a natural fit when it comes to potential trade partners. Yet the Cards are in on a ton of different pitchers, according to MLBTradeRumors.com, so they may shy away from Lester should the asking price be too high.
Despite the emergence of the Pirates as serious contenders for Lester over the past 24 hours, most Lester rumors still link back to Boston's old trading partner, the Dodgers. Los Angeles is looking to clear some of the congestion in its outfield, has several top prospects to offer and is in a competitive race for the NL West crown.
Pairing Lester with Clayton Kershaw and Zack Greinke would be downright unfair to the competition should the Dodgers reach the postseason, so it's easy to see why the Dodgers would be tempted to make such a deal.
CBSSports.com's Jon Heyman cited one "rival GM" as calling the Dodgers "still the best fit" for Lester in a post on Tuesday, naming Joc Pederson and Julio Urias as two potentially attractive pieces going back to the Red Sox.
There are also the never-ending Matt Kemp-for-Lester rumors to consider, but for that I'll simply leave you with this outstanding breakdown by Marc Normandin of Over the Monster.
Last, and perhaps in this case also least, we have the A's, who are somewhat of a surprise contender given their earlier trade with the Cubs for Jeff Samardzija and Jason Hammel. As SI.com's Jay Jaffe notes, the A's could attempt to entice Boston with prospects like Daniel Robertson and Renato Nunez, plus young players with some upside like Drew Pomeranz.
That seems pretty unlikely, though, and unless a third team gets involved, it's tough to see the Athletics and the Red Sox matching up.
Instead, the bet here is that Lester does indeed end up with the Pirates or the Dodgers by the end of the day on Thursday, with the Sox acquiring a major leaguer, a prominent prospect and a lesser prospect in return. Maybe that's Kemp, Zach Lee and a reliever. Maybe it's Jose Tabata, Josh Bell and Nick Kingham. Maybe we've yet to hear of the players who will be involved in the end.
But either way, Lester appears as good as gone from the Red Sox. And while he's professed a willingness to re-sign with Boston even if traded, the odds of that happening are rather slim.
And yes, we've heard some trade rumors about other players on the Sox, too. WEEI.com's Bradford told us on Tuesday that the Kansas City Royals were no longer in on Jonny Gomes, who they'd been linked to over the past week. And in the same piece, Bradford states that the Royals are interested in Andrew Miller, who is perhaps the player most likely to be dealt aside from Lester over the next two days.
But from now until Thursday, everything Boston does will revolve around Lester and the potential franchise-altering move that Ben Cherington and company are about to make.
There's a real opportunity to add more young talent to an exciting nucleus here, and to position the Red Sox for success in 2016 and beyond. But miss on this trade, and the Sox will be depriving themselves of arguably their best player for the next few seasons, and they won't have so much as a draft pick to show for him.
That reality is what's going to make the trade deadline such a tense one in Boston, as a city prepares to say goodbye to one of the most celebrated and popular Red Sox in recent years.