By Neil deMause

We're most of the way through free-agent season now, and it's even more clear that this will be remembered as the Winter of Robinson Cano. The Mariners' signing of the five-time All-Star not only set off cascade effects in Seattle, where the M's grabbed Corey Hart and Logan Morrison to continue the overhaul of their offense (and, in a less positive direction, their defense), and New York, where the Yankees have now collected every outfielder on the face of the earth but may be forced to spend a season with a second baseman assembled from bits of Kelly Johnson and what's left of Brian Roberts -- but it also ratcheted up yet again baseball's top salary standards: Cano's haul of $240 million over 10 years ties Albert Pujols for the highest total contract value ever for any MLB player not named Alex Rodriguez.

The obvious question: Was it worth it? It's a tough question to guess at in advance, made even tougher by the fact that, as we discussed here earlier this month, there are a couple of competing ways of looking at "worth." It's two questions, really: Is Cano worth more in wins than the Mariners could get by spending $24 million on something else? And will he sell enough tickets (and beers, and TV ads, and Robinson Cano sublimated plaques) to enable the Mariners to pay off his mammoth contract?

My conclusion two weeks ago to the second question indicated no: Each extra win appears to be worth at best $1.5 million in new revenue, and Cano, even if he somehow keeps up his 7-9 win pace of recent season (per Baseball-Reference's Wins Above Replacement stat) well into his 30s, is going to cost the M's close to double that.

That initial answer may have been too simple, though. As Vince Gennaro, Society of American Baseball Research president and author of the 2007 book Diamond Dollars, points out, revenue-per-win varies by team, with some franchises able to leverage a pennant race or postseason appearance into greater riches than others. (Or, if you prefer, some teams have less fickle fan bases that make losing less painful, but also winning less advantageous.) The value of wins that help push a team like the Yankees into the postseason, says Gennaro, could be substantially higher: "I wouldn't be surprised if the 88th and 89th wins for the Yankees aren't nine- or ten-million-dollar wins."

Gennaro uses a slightly different methodology than Graham Tyler, whose work I have cited here previously (and Tyler, for his part, referenced Gennaro's work in his paper -- it's all one big, happy math family here), but Tyler likewise found higher benefits to the Yankees, meaning that the signings of Jacoby Ellsbury and Carlos Beltran for otherwise-ridiculous figures might come closer to paying off in sales of those $2,000 box seats -- though it makes big-money signings by low-marginal-revenue teams or those with slim postseason hopes even more baffling.

So could Cano actually be worth $24 million a year to the Mariners? "I still don't think you can get anywhere close," in new revenue stemming from any potential Seattle postseason appearances, says Gennaro. "It's a very tough one to justify."

Then there's the question of wins, which Gennaro acknowledges can be a goal above and beyond profits. ("If you told Mike Ilitch, the owner of the Tigers, that he could have one championship and $100 million less when he dies, he'd probably take that in a heartbeat.") If Cano keeps up his recent production in Seattle - which at age 31, even if his raw numbers go down from losing the short porch in the Bronx, he should be able to manage at least for his first couple years in the Northwest -- he should be worth about eight wins a year, which in 2013 would have been enough to push the M's all the way to third place, 17 games out of first. Add in Hart and Morrison and a full year from rookie shortstop Brad Miller and even a potential acquisition of David Price and you're still running the risk of spending $24 million a year just to trade up to a better brand of mediocrity.

Maybe an even more useful way to look at this, though, isn't to try to guess the future, but to look to the past. Let's take the 10 priciest baseball contracts in history by total value through the start of the 2012 season (because gauging the success or failure of a deal just signed last year is as much fortune-telling as guessing how Cano will turn out). How have previous contract record-breakers fared, and what do they bode for this year's big signing?

Alex Rodriguez (2001, $252 million/10 years, average annual value $25.2m)

Coming off the 2000 season, A-Rod was maybe the hottest free-agent commodity in the history of the game: Just 25 years old, coming off a year in which he hit .316 with 41 homers as a shortstop. He was rewarded by Texas Rangers owner Tom Hicks with a deal that still ranks as the second-largest of all time, more than a decade later. Over the next 10 years, Rodriguez would win three AL MVPs (one in Texas, two after his trade to the Yankees) and rack up 76.1 WAR, for a cost of about $3.3m/win. Hicks later regretted the signing as "dumb," but it's tough to argue that his teams could have expected any more out of A-Rod than they got.

Derek Jeter (2001, $189 million/10 years, AAV $18.9m)

Two months after A-Rod left Texas, his 26-year-old future teammate cashed in with a mega-deal of his own, coming off a third straight 200-hit season. Jeter was one of the best shortstops in the league at the time, and continued to be so for the life of his contract, clearing the .300 mark seven times out of 10 years, and accumulating 48.7 WAR, or $3.9m/win. Given that the Yankees won seven division titles and went to the Series three times in that span, that Jeter has been the most popular Yankee since the guy who built the old stadium, and that franchise revenues and value more than doubled, the Steinbrennertariat was no doubt happy with its investment.

Manny Ramirez (2001, $160 million/8 years, AAV $20m)

Before he became a walking punchline, Ramirez could hit: If he had retired a couple of years sooner, he'd have finished up with an OPS over 1.000, one of only nine players in history to manage that feat. After leaving Cleveland as a free agent in 2001, he was coming off two of the most dominant hitting seasons in MLB history, with 165 RBIs in 1999 and a .697 slugging percentage in 2000. Manny picked right up where he left off in Boston, racking up 30.7 WAR in eight seasons despite a glove that would have had to work its way up through tin and bronze to iron. That's a pretty pricey cost per win -- more than $5m per -- but two World Series titles and 793 straight sellouts will salve a lot of monetary wounds. The Sox likely could have spent their money better in retrospect, but at least the results were good.

Alex Rodriguez (2008, $275 million/10 years, AAV $27.5m)

Seven years after his big payday in Texas, A-Rod broke his own record by opting out of his contract with three years remaining and signing another 10-year deal. He was 32 years old at this point, and though coming off his third MVP season, wasn't a good bet to repeat; indeed, he had never hit more than 35 homers again after averaging 47 in the previous seven years. Over the first six years of his new deal, Rodriguez has provided a mere 22 WAR, and doesn't look set to produce many more; off the field, needless to say, he has been a non-stop PR disaster. The Yankees may have been counting on a big payday by selling tickets to fans eager to see A-Rod chase the career home run record, but as things stand now, they would have been better off scheduling a weekly A-Rod Complimentary Rotting Fruit Day.

Mark Teixeira (2009, $180 million/8 years, AAV $22.5m)

Getting tired of the Yankees on this list? Remember what Gennaro said about revenue-per-win varying by team. Anyway, Teixeira was the A-Rod of the 2008-09 free-agent crop, coming off what was by WAR his best season yet, and was rewarded by becoming the third-highest-paid Yankee. Only 28 years old at the time, Teixeira tailed off slightly upon arriving in the Bronx, keeping his power but losing about 50 points of batting average. His WAR total for the first five years of his eight-year deal is 16.3, for a cost/win of nearly $9 million, unsustainable even in Gennaro's wildest revenue dreams. (He did get to share that 2009 championship, but we can't credit everybody as being the difference-maker there; they might have won it all even with Jason Giambi at first base for all we know.) As for his intangible revenue creation, I do know one kid with a Mark Teixeira T-shirt; the fact that I think of him as "that kid who has a Mark Teixeira T-shirt" tells you all you need to know about Tex's marketing magic.

CC Sabathia (2009, $161 million/7 years, AAV $23m)

All done with Yankees after this, I swear. Brian Cashman's other big signing of the winter of 2008-09 was the pitching version of Teixeira: 28 years old and coming off his best season to date (6.8 WAR, split between Cleveland and Milwaukee). CC won 59 games over the next three seasons, lost several miles per hour off his fastball, and is now either going to follow the savvy revitalized-ace career path or the arm-fell-off one. (His top comparables through age 32 according to Baseball Reference are Greg Maddux and Dave McNally, which, yeah, that's about right.) He has been worth 22.1 wins over the first five years of his deal, which blows Teixeira out of the water, at least, but unless he can regain his 2009-11 form for the next two seasons, those $161 million in paychecks are going to look a bit pricey.

Joe Mauer (2011, $184 million/8 years, AAV $23m)

Following the 2010 season, the 27-year-old Mauer was one year removed from an MVP season in which he did absolutely everything, leading the league in batting average, on-base percentage and slugging percentage, while playing Gold Glove defense behind the plate. He was rewarded with the biggest Twins contract ever (not a really competitive field, admittedly), then immediately suffered through an injury-plagued season that saw him booed by his hometown fans. He bounced back to his usual hitting levels after that, but thanks to lingering injury issues the Twins have announced that they'll move Mauer to first base, where he suddenly goes from being the best-hitting catcher of his generation to a latter-day John Olerud. That's not without value, but it's hard to argue that his value is $23 million a year, even if a 35-year-old Mauer can still sell T-shirts.

Albert Pujols (2012, $240 million/10 years, AAV $24m)

Pujols' signing by the Angels two winters ago might be the most direct parallel to Cano: same age, same all-world status, same average salary, same 10-year span. As such, it should terrify Seattle fans. While Pujols' subsequent decline has looked even worse thanks to the bat-suppressing environment of Angel Stadium, he's still at best an above-average first baseman at this point in his career, with little hope of fully regaining his three-time MVP stroke. And that's now, at age 33; by the time he's 41, Pujols is likely to be little more than a $24 million line item on the Angels budget for a batting coach or Oldtimers' Game participant. The team that let him go, meanwhile, has remained a perennial postseason participant and seen its revenue continue to climb, making the real winners in the Pujols derby look to be all the teams that didn't sign Pujols.

Prince Fielder (2012, $214 million/nine years, AAV $23.8m)

Fielder signed at a younger age than Pujols (27), but was also never the same player, with zero range in the field (is it possible to have negative range?) and an inconsistent bat. He had one great year in Detroit, one moderately lousy one, and was shipped off to Texas along with a suitcase full of cash for Ian Kinsler. Unless Fielder can convert himself to a David Ortiz-level DH in short order, this contract is going to be somebody's problem for a long time: If this is how Fielder plays defense at age 29, can you imagine what he'll be like when he's 37?

Matt Kemp (2012, $160 million/8 years, AAV $20m)

Speaking of ideas that sounded good at the time: In 2011 Kemp was coming off one of the great all-time seasons, leading the NL in homers, runs scored and RBIs while batting .324 in the batting dead zone known as Dodger Stadium. He was amply rewarded, then immediately hurt his hamstring, and then his knee, at which point the Dodgers realized that even when he was healthy before 2011 he had hardly set the world on fire, and began shopping him around as a trade chip before backing off. Given that Kemp will have to be a 4-5 win player to come close to justifying that contract, and he has managed that exactly twice in his eight-year career, the Dodgers might want to reconsider their reconsideration.

The overall lesson here: If you want a $200 million contract to pay off, make sure you're getting one of the proven best players on earth, someone well under 30, or both, who plays a position where he's likely to age well, and be a team that is on the cusp on greatness and able to cash in by selling high-priced seats and cable eyeballs. The Mariners' Cano signing qualifies on one, maybe one-and-a-half counts. Odds are, it won't be a historic boat anchor, but it also won't be the best way for Seattle to either win the most games or make the most money.

Part of the explanation, says Gennaro, may be that teams are spending more freely in the wake of the new national TV deals that put nearly an extra $30 million in each team's pocket this winter -- something that makes zero sense from a rational economic perspective, since that's money they'll earn even with a team of no-names, but that's not necessarily how team owners think. "I think a rational person in another business that didn't have as much ego attached to it might think, 'How do I optimize the value of $30 million?'" he says. "These guys are more inclined to say, 'Do I invest it in payroll?'"

Gennaro suggests that there are probably smarter ways to spend money, such as, say, building a Latin American development and educational system to snag up-and-coming players at a discount. "All that sounds great," he says, but "the quick fix, the drug is the free-agent market, because it's fast." Even if it is a bit wack.

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Neil deMause is a Brooklyn-based journalist who has covered sports economics for Slate, the Village VoiceBaseball Prospectus and a bunch of other places you wouldn't remember. He runs the stadium news website Field of Schemes, and co-authored the book of the same name.