How did we get here?
Well, the Red Sox lowballed Lester with a reported four-year, $70 million offer in Spring Training, chump change at a time when a less-accomplished pitcher in Homer Bailey got the same average annual value ($17.5 million) over six years from the small-market Reds.
That said, while the actual offer to Lester was a non-starter (and, some would say, an insult), the overall stance made sense. Financial prudence with guys on the wrong side of 30 is, after all, how the Red Sox put together a World Series-caliber club in 2013, when they, quite literally, didn't overextend themselves on aging veterans.
But if reports of Boston only moderately upping that offer over the course of the year are true, it was not exactly time well spent on the part of the Sox, because Lester, with a 2.52 ERA over 21 starts in what is clearly the best season of his career, has put himself in prime position to find the market money he seeks.
So now the Red Sox really have no choice but to trade him. The potential Draft pick compensation should Lester depart in free agency is negligible for an elite organization perpetually built to win now, and trading Lester won't preclude them from engaging with Lester in offseason contract talks. If Boston can get one upper-echelon prospect -- preferably an impact outfield bat -- in exchange for its ace in this hangover season, it's worth whatever emotion is expended.
From the perspective of contending teams, as the David Price banter gets continually loaded with caveats (the Rays won again Monday night), Lester arguably becomes the market's most accessible, attractive commodity -- an elite left-handed arm with two months of contractual control and, therefore, a more palatable price tag.
Here are the six scenarios in which the price tag is well worth it:
1. Pirates. They've built not only a contending club in a market that was starved for playoff baseball for far too long, but the Bucs also own one of the deeper and more dynamic farm systems in the sport. Time to capitalize. Pittsburgh woke Tuesday with just a two-game deficit in a winnable National League Central. The Brewers are sputtering, 8-15 in July. The Cardinals haven't hit all season and are likely without Michael Wacha until early September and Yadier Molina until late September. The Reds have won just one game since the All-Star break to fall below .500.
Pittsburgh needs to pounce, and in Josh Bell, Austin Meadows and Harold Ramirez, it has outfield trade chips that are both attractive and expendable, given the long-term contractual control the Pirates hold on Andrew McCutchen, Starling Marte and Gregory Polanco. Pair Lester with Gerrit Cole, who just made a successful first rehab start in Triple-A on Monday night, and you've got a top-of-the-rotation pair capable of leading you through October.
2. Dodgers. They probably had (and still have) the best shot at landing Price, given their general lack of financial limitations and their prized prospect stash that includes three of the Top 20 Prospects from MLB.com's updated rankings.
Vying for Lester might be a satisfying alternative for the Dodgers, as they could probably get a deal done by only dealing one (not two) of the three from shortstop Corey Seager (ranked No. 17), left-hander Julio Urias (No. 18) and outfielder Joc Pederson (No. 19). Recent struggles for Dan Haren underscore the merits of such a move. Maybe the Dodgers and Red Sox could -- as they did in 2012 -- get really creative with a trade that involves Matt Kemp, but Boston's top priority is (and should be) acquiring young players with big upside, not old players with big contracts.
3. Mariners. Thirteen years removed from their last playoff appearance, the M's have to acknowledge that the American League West title is out of reach, but an AL Wild Card run is worth the effort. Even after the Kendrys Morales addition, their biggest need remains a bat. But with slim pickings in that particular marketplace, another elite arm to pair with Felix Hernandez and Hisashi Iwakuma would ensure that if Seattle is able to escape the AL Wild Card Game, it would still be well-positioned for a best-of-five AL Division Series set.
The question is what specific package it would take to get it done. Even amid shoulder issues, Taijuan Walker and left-hander James Paxton are enticing trade chips. Either of them could be the centerpiece of a deal. In this particular instance, one wonders how much value the Red Sox would place on outfielders Gabriel Guerrero and Austin Wilson, who MLB.com's analyst Jim Callis deemed to be in the "high-risk/high-reward" vein.
4. Cardinals. Maybe the Cards prefer a bat over an arm at this stage, though their right-field logjam complicates things, and Kolten Wong's recent improvement probably nullifies their search for a second or third baseman. What the Cardinals can't ignore is the toll Wacha's injury has taken on the rotation's endurance and, ergo, the bullpen's workload. St. Louis has the NL's fifth-highest relief innings tally since June 18, the day after Wacha's last start.
Lester could certainly reverse that trend, though, and if I'm general manager John Mozeliak, there's no way I'd part with six years of Oscar Taveras for two months of Lester, no matter how shaky Taveras' early results have been. A preferable option might be to make one of the Cards' other on-the-cusp outfielders -- Stephen Piscotty, James Ramsey or Randal Grichuk -- available as the centerpiece of a deal for Lester. Really, the primary takeaway here is that St. Louis has both the trade options and the need for a move of this magnitude.
5. Orioles and Blue Jays. The merits of such a move are obvious for the first-place O's and second-place Jays, both of whom would benefit from another top-of-the-rotation option. But realistically, the Red Sox would have to be completely overwhelmed to deal within their division.
Of the two clubs, the Orioles probably have the better chance of putting a satisfying package together, but they haven't shown much willingness to part with their young pitching, which includes Kevin Gausman, Dylan Bundy, Hunter Harvey and Eduardo Rodriguez. As an alternative, maybe they could build something around outfielder Dariel Alvarez, first baseman Christian Walker or young lefty Tim Berry, but, again, intradivision trades of this magnitude are especially difficult to nail down.
6. Giants. Going back to June 1, San Francisco has a 4.14 starters' ERA, versus a 3.10 mark from the rival Dodgers. This is a discrepancy the Giants would love to address, but they also have a hole at second base that they'd love to address, too. San Francisco has a solid system with particular depth in pitching prospects, and that tends to go a long way in July. Three years ago, the Giants traded top pitching prospect Zack Wheeler for two months of Carlos Beltran. Would they go a similar route with 2013 first-round Draft pick Kyle Crick or '14 top pick Tyler Beede? It's a big question.
But if the Red Sox specifically target a bat, there might not be a match here, as arguably the best one San Francisco has to offer is catcher Andrew Susac, and Boston recently handed the catching keys over to highly regarded prospect Christian Vazquez.