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If the Red Sox won't pay up for Jon Lester, will they pay for anyone?

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The Red Sox' search for an ace probably isn't as simple as throwing the unused Lester money at someone, either now or a year from now.

Johnny Cueto is incredible, and could cost even more than Lester.
Johnny Cueto is incredible, and could cost even more than Lester.
David Kohl-USA TODAY Sports

The Red Sox offered Jon Lester six years and $135 million to return to Boston, and he declined to do so. They offered the free agent they are most familiar with -- and most likely the most comfortable with given that familiarity -- a sixth year and $22.5 million per season, and it wasn't enough to get the job done. This isn't brought up to reignite debate over how much Lester was worth, or whether he should have been offered more, or if the Red Sox were right to stop where they did. The question worth pondering now is whether this offer to the greatest pitcher Boston has developed in decades, this offer that wasn't good enough to reunite the two, was something that was only available to Jon Lester.

The Red Sox have signed a pitcher to a major six-year deal just twice before. Former general manager Dan Duquette traded for Pedro Martinez before the 1998 season, and then signed him to a six-year, $75 million contract with an option for a seventh year. Pedro was new to the Sox, but he was not new to Duke, who had already pried him loose from the Dodgers in November of 1993 back when he was the GM of the Montreal Expos. In this way, Pedro was similar to Lester and these Red Sox, as the front office was familiar with his background and how he worked and handled himself off the field in addition to his stellar performances on it. There were also key differences worth noting here, though, chiefly that Martinez was still under control for a year and therefore negotiating from a different position, as well as his being just 26 at the time: Martinez became a free agent for the first time at 33, seven years after signing this extension, whereas Lester's first post-free agency season will be his age-31 campaign. Also, he was Pedro Martinez as we know him already, as he won his first Cy Young in 1997 while posting a 1.90 ERA over 241 innings for the Expos. Lester is tremendous, but he's no Pedro.

Don't feel bad, Jon, no one is Pedro. Especially Daisuke Matsuzaka, the other pitcher to end up with a six-year deal in Boston. It is worth pointing out, though, that Dice-K's contract, like Pedro's, does not fit in with the present-day market. Someone with his upside is going to get six years still, but Matsuzaka was being paid like he could be an above-average pitcher, not a rotation leader. The still somewhat unknown expectations for Japanese pitchers at the time allowed such a thing, even when his ceiling suggested there could be more to him than that, and the limitless posting fees of the time also complicated matters in a way they won't today.

That was the lone six-year deal for a pitcher during Theo Epstein's tenure, with the Sox instead playing it somewhat safe with free agent pitchers for a while. They traded for Curt Schilling, then extended him for four years with an option for a fifth. They let Martinez walk due to injury concerns and the knowledge the Mets would keep tacking on years to their offer, years the Sox were not comfortable guaranteeing. They also let the erratic Derek Lowe leave, and settled for the less expensive Matt Clement to replace him. When these sorts of moves -- Schilling aside -- didn't work out as hoped, the Sox went shopping for a young ace once more, settling on the Marlins' Josh Beckett. He was signed to a three-year deal with an option, and then a five-year extension in 2010, the second five-year deal handed out by Epstein's Sox. The first was for free agent John Lackey, who signed for five years and $82.5 million with an insurance option for a sixth year that would be triggered by a recurrence of his elbow problems.

Lackey
Photo credit: Kim Klement-USA TODAY Sports

Cherington's history with these deals is even shorter: the closest the Red Sox have come to a long-term deal for a high-end pitcher is the offer they just made to Lester. That guarantees nothing about their future under Cherington, but it is something to remember when assuming that Lester's replacement at the top of the rotation is going to come from free agency and Boston's deep pockets.

James Shields should only require five years, and maybe even just four, as he'll be 33 years old in 2015. Max Scherzer is going to cost upwards of $200 million and probably seven years, never mind six. Those are the remaining aces this winter with Lester off the market, and while there will be more available a year from now, they're probably out of Boston's price range just like Lester was. Johnny Cueto is incredible when he's on the mound, and will be just 30 years old in the first season of his new deal, but he's also missed time with injuries on a few occasions, making him a real risk for a long-term deal. At the same time, he's second to Clayton Kershaw in ERA+ since 2011 (155), so someone is going to take that risk with gusto. It probably won't be the Sox. Jordan Zimmermann could also price himself out of Boston if he has another Zimmermann-esque campaign in 2015.

Doug Fister will be playing the James Shields' role of dependable veteran you could live with atop your rotation, but he'll be 32 instead of 33 and is therefore a potential six-year guy if the market gets a little nutty. Yovani Gallardo will be 30, but he's not an ace so much as a guy who has run mostly unopposed for the position in Milwaukee. Zack Greinke could be available, but if he's opting out of his six-year, $147 million deal, it's to sign a lengthier, more lucrative deal, only this time when he's a few years older. Mat Latos is more of a two than an ace, Jeff Samardzija is going to get one of the biggest deals of the offseason, Hisashi Iwakuma will be 35... there are no guarantees the Red Sox end up with, or are willing to end up with, any of these players on the contracts they will command, which is part of why Lester was so appealing to begin with.

Maybe the Sox trade for one of them this offseason and, after a season working with whichever of them it is, feel they are worthy of a six-year deal for Lester money. Maybe losing Lester, and whatever that causes to happen in 2015, makes them feel better or worse about their decision, so they stay the course or make necessary adjustments to their philosophy based on that. The most-likely scenarios, though, are the ones where they grab James Shields now while they can get someone for fewer than six years, or simply hope one of their own arms or one they trade for can develop into a dependable, rotation-leading arm before they get expensive. That's mostly been how the Sox have done things for years now, and it's worked out well. They might even already have that guy in Rick Porcello, though, there are some major questions yet to be answered there.

Let's be honest here. We -- meaning any of us who are not working for the Red Sox -- likely just don't know who Boston would pay up for if not Jon Lester, and that makes us all a little nervous in the wake of his departure. Someone like Jose Fernandez could hit free agency in their mid-to-late 20s, making the decision to go long-term easier for the Sox, who can bid with anyone if they have the desire. The prospects could fail to be what they need to be, forcing Boston to spend on someone a little older when they would prefer not to. It's not impossible that the Sox trade for someone like Jordan Zimmermann and then decide to pay him what it will take to keep him around, or find the next Beckett a year or two down the road. Failure to sign Lester doesn't tell us that the Red Sox will never pay for a big-money pitcher, but it is a reminder that this sort of thing isn't automatic just because they have the budget. The Red Sox were willing to bring Lester back because he was their best option. The next time someone that pricey is their best option, they'll likely be willing to jump in again. Whether that will work better or the same as it did for Lester is just something we'll have to wait to find out.