Rarely does an elite starting pitcher change zip codes in the week leading up to the trade deadline, especially one that was part of a world championship team the year before. However the Boston Red Sox find themselves in a difficult situation with their ace Jon Lester who is set for a major payday as a free agent this winter. There’s mutual interest in keeping the southpaw in Beantown, but the two sides weren’t able to agree to an extension in Spring Training and a deal before the end of the season seems unlikely at this point. The 48-57 Red Sox have already dealt one of their starters, Jake Peavy, and should take advantage of a market inefficiency and deal Lester before July 31st as well.

Lester, 30, is in the midst of an outstanding season in which he’s posted a 2.52 ERA and a 2.63 FIP in 143 innings pitched. His 4.5 fWAR on the season has already eclipsed last year’s mark of 4.2. The Red Sox second-round pick in the 2002 amateur draft is owed around $4 million for the remainder of the season and is all but guaranteed to receive a qualifying offer should he remain with the organization beyond the deadline. There’s no question that Lester would be a significant addition to any team looking for starting pitching help, and there are plenty, and could easily be the best available starter given the uncertainty surrounding David Price.

The Tampa Bay Rays have been on a hot streak of late and have propelled themselves within a few games of a wild card spot and may prefer to hold on to their ace for the stretch run. Reports indicate that they need to be blown away by an offer for their star and have yet to be. The major point of contention for the Rays, no doubt, is Price’s salary is expected to be in the $20 million range for the 2015 season, his last year of club control before hitting free agency. The Rays are built to win now however, and at this point in time he seems more likely to be dealt in the offseason. Although plenty could change before Thursday’s deadline.

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[pullquote]Lester owns a 110-63 record in 241 starts across nine big league seasons. His 33.7 career fWAR is 15th among active pitchers and is ahead of both Cole Hamels and Clayton Kershaw.[/pullquote]

We do know that Tampa Bay is looking for a blue chip prospect, see the Seattle Mariners Taijuan Walker, as well as a couple other pieces in exchange for Price considering the acquiring team would have an extra year of control. Lester would be a pure rental should he be dealt this week and the acquiring team wouldn’t be able to cash in a draft pick if he signed elsewhere as he’d be ineligible to receive a qualifying offer at season’s end. So what would two months of Lester cost? A lot.

Perhaps the best comparison for a Lester deal would be the July 2012 trade that sent Zack Greinke from the Milwaukee Brewers to the Los Angeles Angels. In exchange for two months of Greinke the Brewers received Jean Segura, Johnny Hellweg, and Ariel Pena. Segura was ranked No. 55 on Baseball America’s Top 100 Prospects list entering the 2012 season and is having a down 2014 after a 3.3 fWAR 2013 campaign for the Brew Crew. Hellweg and Pena are both playing at Triple-A this year and only Hellweg has reached the major league level where he played a handful of games last year.

Greinke had a 3.44 ERA and a 2.53 FIP in 123 innings pitched for the Brewers at the time of the trade so one could argue that two months and a potential playoff run from Lester should net more than what the Angels sent for the right-hander. There’s been a rumor circulating today in which the Red Sox have discussed sending Lester to the Los Angeles Dodgers in a deal involving outfielder Matt Kemp, but several outlets have cooled those reports and nothing appears to be imminent between the two clubs at the moment.

The Dodgers could be a fit for Lester as they’ve also been connected to Price and the idea of sending Clayton Kershaw, Greinke, Lester, and Hyun-jin Ryu out in a playoff series has to be awfully tantalizing. Los Angeles is loath to trade top prospects Joc Pederson and Corey Seager in a trade for Price but may be willing to move one of them in the right deal. One could argue that sending Pederson to Boston in a one-for-one trade for Lester would be an overpayment let alone adding another piece or two to the pie.

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The Giants probably wouldn’t be interested in Lester now that they’ve added Peavy, but the New York Yankees, Toronto Blue Jays, St. Louis Cardinals, and Mariners have had varying levels of interest in adding a top tier starting pitcher according to reports, but it’s unlikely the Red Sox would trade Lester within their own division, even if he is willing to re-sign in Boston despite being dealt.

ESPN’s Buster Olney also tweeted today that the Red Sox are still listening on Lester and would be willing to trade him if their asking price is met, and it could be higher than the draft pick they’d receive if he walked. Well that much was obvious — why would the Sox deal for something less than the first-round pick which would likely be in the No. 30-40 overall range? Stranger things have happened of course, but it’d likely take multiple pieces to land the left-hander.

Seager, the younger brother of Mariner Kyle Seager, entered the year as the No. 37 prospect in baseball according to Baseball America, so a package including him and a couple Double-A types of players that offer some upside would be similar to what the Brewers received for Greinke while accounting for the fact Lester likely has slightly more value. It’s worth noting he’s playoff proven and has had no issue with pitching in the spotlight.

The Cardinals have plenty of prospect currency to deal from but it’s doubtful they’d want to give up an Oscar Taveras or a Carlos Martinez in exchange for two months of Lester. There’s a possibility they’d deal Tavares and another fairly significant piece in exchange for a year and a half of Price, but even that appears slim.

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The defending World Series champions have had a disappointing year riddled with injuries and under-performing prospects and have already started turning their attention to 2015. If they feel their best shot at extending Lester is to hold on to him until the offseason, that’s a chance they’re willing to take. Though considering the southpaw is thought to be looking for a six-year deal in the $140 million range, a la Cole Hamels, and the Sox are said to have offered four years and $70 million in Spring Training, it could be difficult to consummate a deal regardless.

Bottom line: with David Price looking more and more like he’ll stay with the Rays for the time being, Lester would easily be the best available starter on the market and Boston should have no problem picking up at least one elite prospect if not a pair of very good young players in a trade. Or even Kemp or another major league player if those talks end up materializing.

The draft pick would be nice, but the Red Sox are in a position to turn the ship around quick and be serious contenders in 2015. They have plenty of young talent and a solid pool of pitching depth to work with and adding to it would only be a good thing. Considering the potential return Lester could net, Boston should take the risk and deal their ace before the deadline on Thursday. It doesn’t sound as though extending him will be any easier come November and December, and they simply can’t let a player of Lester’s calibre to walk for a draft pick.

Just ask the Yankees about losing Robinson Cano.

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