The Red Sox came into the winter with a clear need for starting pitching, and a lot of money to spend. Yesterday, they spent a big chunk of that money, adding $41 million in AAV to their payrolls for the next four or five years. And yet, today, they still have the same glaring need for starting pitching. Evaluating the wisdom of the Red Sox spending spree is an interesting challenge, because unlike most free agent signings, these feel like half of the transaction.

We can still evaluate the signings of Pablo Sandoval and Hanley Ramirez based on the production the Red Sox should expect going forward and the money that was surrendered to acquire that future production, but we don’t really know the whole picture here. The signings of two of the winter’s premier free agent hitters very likely mean that Yoenis Cespedes is getting traded, and I think Mike Napoli might be on his way out of town too. What the team gets back in trade, and how they choose to reallocate money that could be saved through those trades, will affect what else the Red Sox can choose to do this winter. They know they need pitching, and it seems essentially impossible that they won’t make further moves to address that need; moves that were made possible by these signings.

So without those pieces of information in place, I’m hesitant to draw any strong conclusions about the new contracts given to Sandoval or Ramirez. If the team trades Cespedes and Napoli for young arms, then spends the $25 million in savings on Max Scherzer, then these moves start to more clearly address the team’s need for a frontline starter. But we don’t know if they’re going to do that. We don’t know what they’re going to do, so we can’t be too strongly convicted about whether these signings were a wise use of resources.

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Heading into the 2009 draft, Baseball America wrote the following about Kyle Seager’s future while rating him as the 97th best prospect in the draft.

A three-year starter for North Carolina, Seager is an area scout favorite, not to mention a player opposing coaches respect immensely. National evaluators have a harder time pegging him because he doesn’t fit a neat profile. His best tool is his bat. He has a smooth, balanced swing and makes consistent contact with gap power. He ranked third in the nation in 2008 with 30 doubles and was on a similar pace in 2009. He has a patient approach but doesn’t project to hit for much home run power because of his modest bat speed and flat swing plane. While he’s a fringy runner, he’s a fine baserunner.

Seager played second base for his first two seasons and moved to third this year, where he has played good defense. Featuring an average arm and impressive agility, he’s an average defender at third, if not a tick above. Scouts who like him see a Bill Mueller type who doesn’t fit the profile but grinds out at-bats and outs in the field. His detractors see him as a safe pick with low upside and a future reserve or utility player.

Major League teams agreed with the assessment, and Seager went 82nd overall, sandwiched between Trevor Holder and Jerry Sullivan. He was a classic low upside guy, taken because he looked like he could provide some value with minimal risk, but no one expected Seager to turn into a star.

After three seasons (and some change) in the big leagues, though, it’s probably time to throw that profile out the window. In 2,200 big league plate appearances, Seager has now launched 70 home runs, or an average of 19 longballs per 600 plate appearances. For comparison, Pablo Sandoval has averaged 20 home runs per 600 plate appearances through his career, and has been the focus of a pretty significant bidding war for his services. The market recognizes Sandoval as a significant offensive force, and is paying him as such; given that, we probably have to recognize Seager as a legitimate asset at the plate as well.

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The Red Sox are reportedly on the verge of signing Hanley Ramirez for something “in the range” of $90 million over five years, according to Ken Rosenthal. The vagueness associated with the “range” wording means that we don’t know exactly how many years or how many dollars Ramirez is getting, but it seems like anything in the range of $90 million for Ramirez is going to be a pretty good deal for the Red Sox. That said, we’ll hold off on a full analysis of the contract until we actually know what the contract is going to look like.

So for now, let’s talk about what this move does to the Red Sox roster and the rest of their offseason plans.

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Justin Upton is probably going to get traded. If you believe Joel Sherman’s source, there’s no probably about it; Upton is the next Brave out of town. And it makes sense; the team is clearly retooling for the future, while Upton is entering the final year of his contract. If the Braves don’t think they’re going to sign him long-term, better to trade him now than settle a compensation pick next year.

The question will be the price. Sherman reports that the asking price for Upton is going to be higher than the return they got for Jason Heyward, and that was already a pretty solid package. As I noted this morning, teams are paying through the moon for right-handed power right now, and so Upton will be an attractive option for teams looking to balance out their line-ups.

But even with the advantage of his handedness, I’d like to suggest that the price for Upton should be less than what St. Louis gave up for Heyward. And I promise, this isn’t another discussion of Heyward’s defensive metrics. I can make the point without even needing to cite UZR or DRS, because the offensive gap just isn’t as large as people think. Here are their respective lines over the past three seasons.

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Ten years ago, everyone wanted young pitching. It was the considered the currency of baseball, the thing you could always trade if you needed to acquire something else. But these days, random kids on the street can throw 100 mph, the strike zone is gigantic, and preventing runs is now the easy part of the game. What everyone wants now is offense, and seemingly, offense in the form of good right-handed hitters.

This seems a reaction to the fact that the league’s platoon splits have gotten larger over the last few years; specifically, left-handed hitters have been exploited more often by left-handed pitching. Here is the league average wRC+ for LHP vs LHB match-ups in each year since 2002:

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$325 million. That’s the number that gets your attention, and it should; the contract that Giancarlo Stanton signed with the Marlins is the largest in the history of baseball, and it will span the next 13 years. There are kids currently in first grade who could theoretically get to the big leagues in time to play with Stanton before this contract expires. The $325 million commitment is twice as much as Loria paid to buy the entire Marlins organization back back in 2002. The deal is staggering in both length and cost, but as Jeff Sullivan wrote last week, it’s an entirely reasonable contract for one of the game’s best players.

But there’s another fascinating aspect to Stanton’s contract: the $325 million figure might end up being nothing more than a mirage. Because of the leverage he commanded, and potentially some lingering distrust of the franchise after their last spend-a-bunch-of-money-then-trade-everyone fake out, Stanton’s representatives were able to negotiate an opt out clause into the deal, meaning that he can choose to void the deal after the 2020 season.

If Stanton continues to perform at an elite level, it’s entirely possible that he could void the last half of the deal and land a new contract for even more than this deal guarantees him next decade. After all, Stanton will have just finished his age-30 season when the opt-out decision comes due, and even at that age, elite players are landing 10 year contracts in free agency. Alex Rodriguez used this exact tactic in 2007 to opt-out of the final three years of his initial mega-contract, turning the remaining $72 million into a new 10 year, $275 million contract that the Yankees are still regretting.

Since that deal, the opt-out clause has become an increasing popular request for premium free agents, as Clayton Kershaw, Zack Greinke, and Masahiro Tanaka — among others — have had opt-outs negotiated into their contracts. Greinke’s decision comes next winter, when he’ll have $71 million remaining on the last three years of his deal; assuming he stays healthy and pitches reasonably well in 2015, opting out should be a pretty easy call, given the market price for high quality arms.

And that is exactly why the game’s best players are increasingly asking for these options to be inserted into their deals. For the player, a large guarantee with an opt-out is the ultimate win-win, as they secure a significant paycheck even if their performance declines or they suffer an injury, but they aren’t stuck with a below-market salary over the long term if they play well, or if the economic status of the league improves after they sign their mega-contract.

Read the rest on Just a Bit Outside.

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In yesterday’s write-up of the Jason Heyward/Shelby Miller trade, I wrote this:

Because of how quickly he got to the big leagues, Heyward is in line to hit free agency after his age-25 season, and he’s going to have roughly +25 career WAR when he reaches the open market. Barring a disastrous 2015 season, he’s going to get paid, and you can be certain that his agents will be pointing to the 13 year, $325 million deal that Giancarlo Stanton has agreed to as the new precedent. Sure, Heyward isn’t going to get 13/$325M, given the massive differences in power, but it seems likely that he’ll demand a deal that starts at 10 years and goes north of $200 million.

Robinson Cano got $240 million as a similarly valuable player entering his age-31 season; Heyward might not have Cano’s offensive track record, but he’s going to be selling his prime years, and the deal won’t extend into the period of his career where you’d expect him to essentially be worthless. If the Cardinals want to lock up Heyward before he gets to free agency, it’s probably going to take something like the contract they refused to give Albert Pujols. Maybe they might be able get him to take a slight pre-free agent discount and get him for 9/$200M or something in that range, but let’s dispel the notion that the Cardinals are going to be able to sign Heyward for anything other than a mountain of cash.

Which generated a lot of responses like this.

Since I basically just made the claim without any evidence to support it, I figure it’s on me to actually back up my assertion. So, let’s go through and see if we can estimate what Jason Heyward’s market price would be as a free agent next winter.

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Maybe we should have seen this coming. It was pretty clear that the Braves were going to trade an outfielder this winter, with both Justin Upton and Jason Heyward entering their final season before they became free agents, and the team apparently preferring to employ Evan Gattis as a left fielder rather than as a catcher. The team tried to re-sign Heyward when they spent last year locking up their young core, but found his price prohibitive, so he almost certainly wasn’t staying in Atlanta beyond the 2015 season, and the Braves probably aren’t good enough to be pushing all of their chips in for the upcoming season.

So, trading Heyward now makes a good amount of sense for the Braves, and they made it clear that acquiring starting pitching was their #1 priority this winter. A natural trade partner would have a hole in right field, some rotation depth, and the potential desire and ability to try and sign Heyward to a long-term deal before hit the open market next winter. No team in baseball fit that description as well as the St. Louis Cardinals, so while we didn’t hear any pre-deal rumors of the deal that sent Shelby Miller and Tyrell Jenkins to Atlanta for Heyward and Jordan Walden, it feels like we should have anticipated something like this. It’s the kind of move that seemingly makes a lot of sense for both sides.

We’ll start with the Cardinals side of things, since they’re acquiring the best player in this deal. Jason Heyward is a stud, and you don’t even have to buy into defensive metrics to agree with that statement. For 2015, Steamer projects him at +4.5 WAR per 600 plate appearances, the 16th highest total of any position player in baseball, and that’s with him grading out as just a slightly above average defender: the +10 fielding projection right field adds up to a +3.5 DEF rating, which includes the positional adjustment for playing a corner spot. In terms of forecast defensive value, Heyward’s projection puts him in roughly a similar group to guys like David Wright, Robinson Cano, Pablo Sandoval, and Josh Reddick.

It’s also a significant step back from what he’s done previously, as his career DEF/600 PA rating is +10. In other words, Steamer is projecting Heyward to take a big step back defensively and still be one of the best players in the game, because the forecast sees a 25 year old with a career 117 wRC+ and positive contact rate trends, so it thinks Heyward is on the verge of a big offensive breakout. From a purely offensive standpoint, Steamer expects Heyward to be as good (or slightly better than) the good Upton, Matt Kemp, Ryan Braun, or Hanley Ramirez. If you combine the offensive level of those players with above average defensive value, well, you’re left with a superstar.

And that’s why the Cardinals have to be pretty thrilled with this move. They’re legitimately getting one of the best young players in baseball, and at the only position where they had a glaring need. Adding Heyward to fill their right field hole will end up being one of the largest improvements any team makes this winter. The question for the Cardinals is how long they’ll get to keep him.

Because of how quickly he got to the big leagues, Heyward is in line to hit free agency after his age-25 season, and he’s going to have roughly +25 career WAR when he reaches the open market. Barring a disastrous 2015 season, he’s going to get paid, and you can be certain that his agents will be pointing to the 13 year, $325 million deal that Giancarlo Stanton has agreed to as the new precedent. Sure, Heyward isn’t going to get 13/$325M, given the massive differences in power, but it seems likely that he’ll demand a deal that starts at 10 years and goes north of $200 million.

Robinson Cano got $240 million as a similarly valuable player entering his age-31 season; Heyward might not have Cano’s offensive track record, but he’s going to be selling his prime years, and the deal won’t extend into the period of his career where you’d expect him to essentially be worthless. If the Cardinals want to lock up Heyward before he gets to free agency, it’s probably going to take something like the contract they refused to give Albert Pujols. Maybe they might be able get him to take a slight pre-free agent discount and get him for 9/$200M or something in that range, but let’s dispel the notion that the Cardinals are going to be able to sign Heyward for anything other than a mountain of cash.

The team definitely has the means to take on a contract like that. They only have $73 million in committed contracts for next season, and Matt Holliday’s contract expires at the end of the 2016 season, so they have the flexibility to make Heyward a franchise-player type offer. And they do have a history of acquiring players on the cusp of free agency, only to convince them to stick around instead, but stretching for a single player the way Heyward will require would be something new for this front office.

For now, this has to be viewed as a rental. A rental with a chance to purchase, perhaps, but this isn’t a trade-and-sign deal like we’ve seen with the R.A. Dickey or Martin Prado trades the last few years. The Cardinals are getting a great right fielder, but they’re only guaranteed to get him for one year, and then it’s either a really large long-term commitment or settling for the compensation pick that comes from letting a premium free agent walk away at year’s end. There’s a non-zero chance that the long-term return on this deal for St. Louis will be minimal.

But the short-term upgrade is huge, especially if they flip Peter Bourjos for a starting pitcher to replace Miller, which shouldn’t be too terribly difficult. Having Heyward/Walden/Pitcher To Be Named instead of Bourjos/Miller/Jenkins could be a three or four win upgrade in 2015, depending on what kind of starter they get in return, and that’s three or four wins in a year in which marginal upgrades are going to be extremely valuable to the Cardinals.

Adam Wainwright is probably just about finished as an ace, and is headed for a decline. Yadier Molina won’t be able to hit forever. Holliday isn’t a spring chicken anymore. The Cardinals have plenty of good young talent, but their best players are getting worse, and the Cardinals needed a significant upgrade to put themselves in position to win the NL Central once again. This move does just that.

The long-term cost will essentially boil down to what you believe Shelby Miller is. Is he a top-flight young pitcher, the guy who has produced +6 WAR by runs allowed in 370 big league innings, and just turned 24? or is he a two-pitch tease, overrated by run prevention, heading for a short-term crash when his mediocre peripherals catch up with him? A strong case could be made for both outcomes.

Miller throws a lot of fastballs up in the zone, and as Eno noted through multiple conversations with pitchers this year, high fastballs can produce some terrific results, often inducing a lot of useless contact that isn’t captured in FIP-type metrics. If Miller’s approach to pitching up with a good fastball makes him a guy who can sustain a BABIP in the .270-.280 range, the underwhelming strikeout rates become a lot less problematic. If you’re a Braves fan who wants to be excited about this deal, here’s the first ~400 IP comparison you want to use.

Cain was always better at home run prevention than Miller, but the template is similar, and it’s certainly possible that Miller is a (somewhat worse) new version of the Cain skillset. If Miller’s FIP-beating ways prove sustainable to a significant degree, picking up four discounted years of a quality young arm is a very solid return for a single year of Heyward, especially if the Braves don’t see themselves as strong contenders in 2015.

But Cain is notable because most pitchers can’t do what he’s done, and not every young hurler who posts a low BABIP for 400 innings is definitely going to follow in his footsteps. Here’s another, less-rosy comparison for Miller, again with career performance through the equivalent of two full seasons.

A couple of years ago, the arguments for Hellickson were the same as they are for Miller today. Maybe he’s just good at inducing a lot of popups, and because he’s a flyball guy, he’s always going to run lower than average BABIPs, so he’s underrated by metrics that focus only on walks, strikeouts, and home runs or ground balls. Hellickson managed to keep things going through age-25, and then promptly fell apart, pitching poorly and getting injured. The Rays just shipped him to Arizona for two lower level prospects rather than bet on him returning to prior form.

More often than not, guys who post big gaps between their ERAs and their FIPs regress towards the latter, which is why FIP and xFIP work for most pitchers. It doesn’t mean Miller is definitely not an outlier, but he probably isn’t at outlier to the degree that he’s been so far, and he’s probably more of an okay pitcher than a very good one.

But even four years of an okay young arm is pretty valuable. After all, we’re looking at league average starters making $10-$12 million per year in free agency, and Miller will a little more than the league minimum this year, with three below-market arbitration years to follow. Even if Miller is more of a solid arm than a future ace, the Braves are getting a lot more quantity of value here, and they’re allocating it into the years where they think they might be more able to contend.

And Miller isn’t the only thing they’re getting. Tyrell Jenkins was a first round pick a couple of years ago, and while he’s battled arm problems since, Kiley McDaniel remains somewhat intrigued by his potential. Here’s Kiley’s updated take on Jenkins:

Jenkins missed the first half of 2014 recovering from shoulder surgery on a muscle in his shoulder (not the joint itself), something that had been bothering him for years. He turned 22 in the middle of this season and was understandably a bit rusty in half a season at High-A, but started to find his stride in the Arizona Fall League, where I scouted him a few weeks ago. He sat 92-94 and hit 96 mph, flashing above average fastball life at times, with an above average 80-83 mph hard curveball and a changeup at 81-84 mph that’s average when he keeps it down in the zone.

He’s incredibly athletic and the breaking ball has flashed plus at higher velocites, so there could still be even more in the tank than what I saw. I’d like to get a full, healthy 2015 on the books for Jenkins before i give a projection with some certainty, but he seems to be headed in the right direction now with enough starter traits to project him in a rotation. I’d grade him as a 50 FV/#4 starter now, but I could edit that up a notch by the middle of next season.

The combination of Miller and Jenkins give the Braves two live-arms that they’re buying somewhat low on, and if both end up pitching to their previously-believed potential, this would turn into a huge win for Atlanta. If either of them turn into quality mid-rotation starters, or if you think Miller is already that now, then this probably is a smart enough move for a somewhat-rebuilding team to divest a short-term asset into some future value.

Of course, if Miller is Hellickson 2.0 instead of Cain 2.0, and Jenkins is just another power arm who can’t miss bats, then this could look pretty terrible for the Braves as well. If Steamer is correct about Hewyard’s impending breakout, this could turn out to be a franchise player for a couple of arms with legitimate question marks who might turn out to be nothing at all. This move could be great, okay, or terrible for Atlanta, and it all depends on how the young arms develop, which is maybe the most difficult thing to project.

The fact that there’s no obvious most likely outcome suggests this is a pretty fair move for both sides. I probably prefer this a little bit from St. Louis’ perspective, since I lean more towards assuming Miller’s strikeout regression is a concern, but even I’d still say this is a fair return for a single year of a player looking at a monster paycheck next winter. The Cardinals get better now, and get a chance to make Heyward the new face of their franchise, while the Braves probaby get better for the future.

And that makes this seem like a smart trade for both teams. The Cardinals get the better player and a chance to extend a player the Braves weren’t going to keep, while the Braves get some good young pitching to make a stronger run in 2016. This is a deal that serves the purposes of both sides. It might end up favoring one or the other, but at the time of the deal, it makes sense for both Atlanta and St. Louis.