The Red Sox are nine games back in the current AL Wild Card standings. It's not where they'd like to be, of course, but they'll have some unfamiliar decisions to make when the trade deadline rolls around. There are already trade rumors about Jake Peavy, but another one of the Red Sox starters might be joining him soon.
Earlier this week, ESPN's Buster Olney reported that the team had resumed extension negotiations with the 30-year-old left hander, but now he believes those negotiations tare "all but over." In other words, Lester looks like he's headed for the open market this winter.
"I think it’s all but over that Jon Lester is going into free agency and I think the only way that they circumvent that is if the Red Sox do what the Phillies did two years ago with Cole Hamels and say, ‘OK, sorry about that. We’re totally wrong and we’re willing to give you a top-of-the-market deal for [$140 million-$150 million],’ and I think there’s no chance of that happening."
Things could have gone differently, but the Red Sox may have waited to long.
"I think that the Red Sox [have made an] effort in the last couple of weeks to put an offer in front of him. The bottom line is that the situation has changed. … If they had gone to him in spring training and said, ‘Look, would you do something like five years and [$100 million-$110 million]?’ which, within the context of Clayton Kershaw getting $215 million, Felix Hernandez getting $175 million, that would have been a nice, fair, team-friendly, middle-of-the-road deal, but that’s not what they did."
So, what do they do now?
It seems as though they have three options. They could step back their current position and take the Cole Hamels route Olney mentioned this year or during the offseason, they could keep him for the rest of the year and recoup the draft pick they would ostensibly earn via the qualifying offer, or they could attempt to trade him for a package they like more than what would probably end up being a late first round pick in the 2015 draft.
That last scenario might not be the most likely, but it's possible. The Red Sox could catch fire and jump right back into the mix for one of the AL Wild Cards, but if things look bleak at the end of the month, gauging the trade market for Lester would be worthwhile even if general manager Ben Cherington has no real intention of moving him.
David Price looks like the biggest name available on the starting pitcher market, but Lester would be highly sought-after if he made it to the trading block. He's having the best year of his career according to both ERA and FIP, and his postseason experience would be a plus for the team's that have a tendency to value intangible things like that.
Placing Lester on the market would also be a subtle way of competing with the Rays as well, despite the fact that both clubs are unlikely to make it to the postseason. If the Red Sox were to make Lester available, they could injure the Rays leverage in trade talks for Price. They could even accomplish that effect to some extent if they pulled Lester back at the last minute and kept him in favor of the qualifying offer or a chance to negotiate an extension with him in the offseason.
No matter what happens with Lester and the Sox, there's sure to be a lot of posturing between now and the point at which a transaction is made.
Actually, that's probably already the case.