MINNEAPOLIS -- Risk goes both ways.
Ever since the Red Sox and Jon Lester agreed to break off contract negotiations at the end of spring training, most of the analysis has focused on the idea that the Red Sox cost themselves tens of millions of dollars by failing to take advantage of a player's self-declared willingness to accept a hometown discount. And with good reason.
Lester has been dominant so far in 2014 on the way to his third All-Star Game. The value to the left-hander of accepting anything less than full market value is dwindling as he edges closer and closer to an opportunity to talk to all 30 teams.
But as brilliantly as Lester has pitched to date, the risks to his own potential earning power -- and, for that matter, the risks of fellow free agent-to-be and 2014 All-Star Max Scherzer, who turned down a six-year, $144 million offer from the Tigers in spring training -- should not be overlooked.
Zack Greinke, who signed a six-year, $144 million contract as a free agent after the 2012 season that will be used as a reference point in negotiations for both Scherzer and Lester this winter, made clear what's at stake in the second half of 2014.
"There's still a long time to go with the season," said Greinke. "Their contracts could go from $100 million to $200 million or $100 million to $20 million over the next two months, depending on how they pitch, if they're healthy and all that stuff."
There's plenty of risk for everyone involved -- particularly given that the potential free agency of Lester comes at an utterly fascinating time on a number of levels, with all kinds of contradictory signals for his market.
Start with this: He's been as dominant as any American League pitcher over the last calendar year. After he struggled for much of the final eight weeks of the first half of 2013, Lester had 10 days between his final start of the first half and his first outing following the All-Star break.
That first start of the second half -- 6 1/3 innings in which he allowed two runs, punched out eight and walked none -- began the best stretch of Lester's career and the best year of any hurler in the American League.
He has made 32 starts, throwing 216 2/3 innings with a 2.62 ERA (second in the AL behind Hisashi Iwakuma, who has a 2.58 ERA in 30 fewer innings), 8.6 strikeouts and 2.1 walks per nine innings. Add in Lester's five postseason starts and he's at 20-10 with a 2.47 ERA with 8.5 strikeouts and 2.1 walks per nine over more than 250 innings.
No one can compare to that ERA. Only David Price can challenge that innings total.
He's been dominant, he's been a workhorse, he's excelled on the biggest stage. He's been consistently brilliant, at a time when elite pitchers are rarely available on the open market.
Teams are locking up their homegrown pitching with tremendous frequency (indeed, Lester helped to define the long-term market for young, pre-arbitration-eligible pitchers with his five-year, $30 million deal signed prior to the 2009 season). There's scarcity of pitchers like Lester. That helps to drive the market for their services and highlights the risk the Red Sox took in not signing him.
"There are so few pitchers who are in the No. 1 category," said agent Scott Boras. "They're just in a different category of the risk you're willing to take because the reward is so great."
Meanwhile, while the Red Sox started negotiations with a four-year, $70 million offer that was more appropriate for the beginning of the 2010 season, when Josh Beckett and the Sox reached a four-year, $68 million agreement, market inflation has been considerable.
"There's a lot of money in the game," noted Greinke. "You still don't know how much money is in the game for how much the owners are making, but obviously they're making a lot because the salaries are still going up."
So: There's tons of money in the game, there are few top players and fewer top pitchers upon whom to spend it, suggesting that the mere mention of Lester's name should be greeted with an audible "cha-ching."
Consider: Of the 81 players named to the All-Star team this year, just 18 (22 percent) have reached free agency -- and a number of those reached free agency as a result of their struggles, when a team decided to release them, rather than when they'd earned the right through six-plus years of big league service time.
So, Lester represents a scarce commodity. The Red Sox ostensibly had a chance to maintain the scarcity of that commodity by keeping him off the market; that outcome appears to be a dwindling likelihood at this point.
But, his potential free agency also arrives at a time when the industry is more aware than ever about the risks of signing pitchers in their 30s, and at a time when pitchers seem to be dropping like fruit flies. Matt Harvey, Masahiro Tanaka, Matt Moore, Jose Fernandez, Kris Medlen, Brandon Beachy, Jarrod Parker, Patrick Corbin, and on, and on ...
The aversion to payroll-choking high-cost risk has taken a number of teams off the market for established stars. Teams are more interested in finding -- and locking up -- the next big thing than they are in securing the services of an established big thing for whom decline is around an invisible corner.
"It seems like teams are more interested in paying younger, less-proven guys," said Greinke. "They're paying more for future performance, where in the past, it seemed like they paid for past performance. So that's one thing tricky in my situation, when you get older. Now, they'll be paying guys according to what they think they'll do for the next five years, not the last five years. That'll be something you'll have to weigh in.
"It's weird it hasn't always been done that way," he added. "It still isn't completely done that way, but it seems that teams are trying to do it more often, and there's more teams refusing to pay for someone that's more on their decline. There's a lot more projecting future talent, it seems like, than how it was in the past."
That's not just a small-market mentality -- though, of course, a number of teams would be priced out of a pitcher like Lester whose market seems likely to sail north of $20 million. Even teams like the Red Sox with robust resources and payrolls are exercising unprecedented caution about top-of-the-market contracts, given the awareness of how drastic a roster swing can occur when a player like John Lackey is an efficient investment (as in 2013) or a player who offers zero return (2012).
And Beckett offers an interesting case study about why the Red Sox might want to exercise caution in their talks with Lester. The team extended the right-hander at the start of the 2010 season. That year proved an injury-driven train wreck.
Had the Sox waited out that season to talk with Beckett, they likely could have retained his services for a fraction of the cost they committed to him at the start of the year. An ill-timed injury for Lester in the second half of 2014, as Greinke noted, could drastically impact the pitcher's earning potential in a way that would suggest that pre-season or mid-season negotiations were imprudent.
Indeed, big-market teams see considerable benefit from walking away from their free agents, even the very good ones. They typically secure a supplemental first-round draft pick if the player is good enough to be granted a qualifying offer, and they avoid making the riskiest forms of investment.
The Sox have exhibited a philosophical preference to let their top free agents walk for most of the tenure of the current ownership group, both under former GM Theo Epstein and current GM Ben Cherington.
"We had more [early-round] picks because of the strategy we employed of walking away from free agents -- which, by the way, also has the added benefit of keeping you away for the most part from albatross contracts," Epstein said recently on the Minor Details podcast. "Players in their 30s decline and you end up paying for past performance. You pay peak prices for a player's decline.
"For most of my time [in Boston], we stayed away from it. It got us in trouble when we didn't at the end. So the added benefit of giving you more bites of the [draft] apple than everyone else, staying away from expensive decline -- more bites of the younger, ripening apple, fewer bites of the older, rotten apple. You combine that with an excellent scouting operation and we did fairly well."
It is undoubtedly true that the Red Sox don't have an in-house successor to Lester as their front-of-the-rotation pitcher. Again, it is worth reiterating: A compelling case can be made that he has been THE BEST pitcher in the American League over a period of 365 days.
But, just because there's not a ready-made alternative does not mean that committing to Lester is free of risk. And therein lies the complexity of the negotiations, the tug-of-war between wanting to retain a pitching anchor and wanting to avoid a potentially bad investment.
And the reality of pitching is that there are no safe bets. There are no risk-free investments. There are only degrees of risk, even for pitchers with established track records. And so, even the suggestion by Lester that he would accept a "hometown discount" represented something other than an obvious course of action for the Red Sox.
Ultimately, the Red Sox may yet conclude that the right move is to re-sign Lester. But the notion that the team followed a terribly misguided course in its conservative approach to negotiations ignores the nature of reasonable risk assessment, or the inherent risks involved in signing a player to a so-called hometown discount.
"It's not my area to try to sign their players, so I don't know, I'm not privy to any of that nor I should be," said Indians and former Red Sox manager Terry Francona. "My guess is that Lester's going to make a lot of money. Not sure where, but my guess is he'll be pretty well compensated, and I know the Red Sox are pretty smart people. Sometimes these things take time. When you're talking about that many millions of dollars, it can't just happen overnight.
"We try real hard to monitor and learn about guys' deliveries, their build, volume, to see if there's any way to maybe get an edge," he added. "I don't care how much you're paying guys. When you lose guys to injuries, it's going to hurt your chances. There's some of the guys that have the cleanest deliveries in the world and they get Tommy John or hurt their shoulders, and there are some guys who have some funky arm action that pitch for years. So you just don't quite know, really."
It is a position that can be difficult to fathom when there is no clear fallback plan. Yet perhaps more than anyone else who has followed the negotiations between the Sox and Lester, it is Lester himself who articulates an almost sympathetic stance to the Sox' position, who seems to accept the idea that a team's hesitancy to extend itself -- even for a discount -- early is neither an indication of insanity nor a stance meant to signal the inevitable end of a career-long relationship.
"Hopefully I come back [to the All-Star Game] a couple of more times to this wearing the same jersey. That's the ultimate goal. All of that nostalgic stuff, this could be last time with that, the last time pitching at Fenway, that's a bridge I guess you'll cross when and if you end up holding a different jersey in front of you," said Lester. "I'm worried about right now pitching for the Red Sox and whatever happens, happens. We're optimistic on everything.
"I get it. I told John [Henry] and the ownership that to their face. This is a business and [they] have a business to run. and when you think about it, I have a business to run," said Lester. "Like I said before, I've expressed it to them, this is where I want to stay. Regardless of whether we do it tomorrow or we wait until the end of the season, this is where I want to be. Hopefully when we get to the end of the season we can figure out something and get it done."