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Counting Pennies and Clipping Coupons in the Bronx

Thirty years of overspending have finally taught the Yankees that the biggest contract isn't always the best one

Friday marks the 36th anniversary of the Seitz decision, a ruling by arbitrator Peter Seitz that stated that any major league player who played one year for a team without a contract became a free agent. The ruling wiped out baseball’s cherished reserve clause, setting the stage for players to earn more money than they ever imagined. From that moment on, one team has been more generous in bestowing those riches than any other: the New York Yankees.

The Yankees are the team that’s synonymous with big spending, so eager to spend big bucks for top talent that they made Catfish Hunter the first big-ticket free agent in baseball history a year before free agency was a thing. They’re the team that has pulled off a big free-agent signing or traded for a big-money player more or less every year, for 36 years in a row.

That New York’s streak might come to an end this year tells us a little about the current crop of free agents, and a lot about how the Yankees do business now.

It’s a shallow group of free agents by historical standards. Only three players will end up with nine-figure contracts, with seven players likely to rake in $50 million or more. The positions those few elite free agents play mostly ran up against the Yankees’ biggest strengths and areas of depth: Mark Teixeira’s got five years left on his $180 million deal and Jesus Montero is poised to become the next star in the Bronx, so there was no room for Albert Pujols and Prince Fielder. Derek Jeter’s nearing the end, but signing Jose Reyes or Jimmy Rollins was still a practical impossibility. A loaded class of closers is irrelevant when you’ve got Mariano Rivera, not to mention nasty setup man David Robertson waiting in the wings.

But the fact that the Yankees were so well covered at these and nearly every other position speaks volumes about the job Brian Cashman has done the past few years. The Yankees have become more adept at recognizing talent, deciding who stays and who goes, and resisting the urge to break the bank or ditch a premium prospect for no good reason than at any other time in years — maybe decades.

From 1982 through 1994, the Yankees missed the playoffs 13 years in a row,1 the team’s longest stretch of futility since Babe Ruth’s arrival. Each failure made George Steinbrenner progressively angrier, more frustrated, and more eager to do something rash. Though the Yankees signed their share of free agents in those days, Steinbrenner’s signature move was to strip-mine the farm system, ordering good prospects to be traded even when the return wasn’t anything special. Trading Doug Drabek and two other players for an aging Rick Rhoden and two relievers was bad. Shipping Jay Buhner to Seattle for Ken Phelps was, as Frank Costanza would tell you, grounds for prosecution.

Then came the dynasty. The Yankees won four World Series in five years, and looked poised to win a fifth in 2001 … until they got Womacked. Losing for years can make a team increasingly antsy to make a big move. But tasting success over and over, then falling just short in heartbreaking fashion, can foster similar levels of angst. The Yankees had brought in plenty of outside help during their four-title run, but acquiring players like Tino Martinez, Paul O’Neill, and Scott Brosius didn’t require massive expenditures of money or talent. After the 2001 loss, Steinbrenner and Cashman started to raise the stakes.

The strategy mostly worked, at first. Homegrown players like Derek Jeter, Andy Pettitte, Bernie Williams, Jorge Posada, and Rivera had grown from up-and-comers to veteran fixtures through the World Series years. But the team’s complementary players started to grow old and increasingly ineffective. Spotting that trend, the Yankees signed Hideki Matsui from Japan, and reaped major benefits. Short-term contracts for still-solid veterans worked out even better than hoped, with Roger Clemens pitching well even as he passed age 40. Less heralded players like Robin Ventura also worked out in pinstripes. The biggest deal of the post-dynasty era also looked like a winner at first. In the first two years of his seven-year, $120 million megacontract, Jason Giambi blasted 82 homers and racked up 12 Wins Above Replacement, giving the Yankees reasonable bang for their copious bucks.

Trouble was, the Yankees weren’t winning; or, at least, they weren’t winning. In 2003, the Yanks notched their sixth straight division title, banked their second straight 100-win season, and made the playoffs for the ninth year in a row. But in the twisted world of Yankeedom, this wasn’t quite enough. Not when one of the greatest moments in franchise history was followed by Josh Beckett serving up a warm plate of STFD. So Cashman started getting even more aggressive.

He traded for Kevin Brown in the 2003-04 offseason, absorbing the $31.5 million Brown was due to make for the next two seasons in the hopes that he had something left at age 39 and 40.2 Brown wasn’t as bad as his 6.50 ERA in 2005 might suggest, yielding a .385 batting average on balls in play that year that was likely due partly to eroding skills, but also to bad luck. Gary Sheffield got a three-year deal extending into his late 30s; Year 1 was a success, Year 2 a disappointment, Year 3 a gigantic disaster. Expecting too much of old players became a damaging theme for the Yankees. But the team overreached in other ways, too. In the offseason of 2004-05, desperately needing capable starting pitchers to patch the rotation, the Yanks spent a combined $61 million on free agents Carl Pavano and Jaret Wright. Wright was terribly injury-prone; Pavano’s health issues were further in his past, but he brought the added risk of being a finesse pitcher coming off success in pitcher-friendly Miami, now going to the Bronx. The two pitchers teamed up to deliver 3.7 WAR over the seven years of their combined contracts.

Maybe it was the trauma of watching Carl Pavano spend four years doing everything other than actually pitch. But the types of deals Cashman made and the types of players he targeted thereafter were dramatically different from what he’d done before. The biggest change was to avoid paying up for old veterans. Cashman may have been learning along with the rest of baseball that players producing at high levels into their late 30s and early 40s wasn’t sustainable. Maybe he was specifically reacting to his own errors. Either way, he came to realize that having more spending power than everyone else only helps if you devote your resources to signing elite players in or near their prime, not older players or those with mediocre talent.

When the Rangers soured on Alex Rodriguez and his huge contract, the Yankees happily flipped Alfonso Soriano for him and got multiple MVP-caliber years for their trouble. When CC Sabathia hit the open market as one of the top pitchers in baseball with youth and unmatched durability on his side, they (smartly) didn’t blink at his $161 million asking price. When Rivera’s deals kept expiring, the Yankees kept re-signing him, because when Mariano Rivera had to pick out the correct Holy Grail he chose wisely. Like any other GM, Cashman still made mistakes. The same offseason he signed Sabathia, he also gifted $82.5 million to A.J. Burnett, a move that looks awful now. He’s also overpaid several incumbent Yankees to stay in town. In those cases, though, other factions may have intervened: We know that Randy Levine insisted on tossing a few extra million into a Jeter three-year deal that had little to no chance of paying off, and that Cashman wanted nothing to do with the $35 million the Yankees foolishly chucked at Rafael Soriano.

Perhaps the biggest change in Cashman’s approach has been the way he values the team’s own prospects. Three years ago, he dealt Jose Tabata and three other young players to Pittsburgh for Damaso Marte and Xavier Nady. Two years ago, he forgot the cardinal rule: Never trade anything of value to bring Javier Vazquez to New York. But Cashman has grown increasingly stingy in his willingness to give up homegrown potential stars. He held on to Robinson Cano for years amid swirling trade speculation and concerns about his young second baseman’s unrefined approach, and got an MVP candidate for his patience. He’s resisted all overtures for phenom Jesus Montero, preferring to let the 22-year-old slugger swing for the fences in Yankee Stadium next year, not somewhere else. Though they might still get dealt at some point, Cashman’s refusal to sell too quickly on pitching prospects Manny Banuelos and Dellin Betances has resulted in both pitchers maturing into hot commodities with big value to both the Yankees and potential suitors. When the team does decide to part with a top prospect, it can only be if an excellent player offering multiple years of team control is available, the way Curtis Granderson was after the 2009 season.

Hanging on to top prospects doesn’t only allow those players time to ripen and potentially become useful players on the big league club. It can also allow the Yankees to save money at select positions, paying half a million to a rookie where they might’ve once paid $10 million to a 38-year-old. If a thrifty approach seems puzzling given the Yankees’ massive revenue streams, consider the new luxury tax codified in the recently ratified collective bargaining agreement. Cashman has his eye squarely on the $189 million luxury tax threshold to avoid paying big penalties; if Montero’s whacking 30 homers a year in New York and making the league minimum, you’ve solved two potential problems at once.

But here’s the real $189 million question: Are prudence and austerity the right ways to run baseball’s marquee franchise? The Yankees have won just one World Series in the past 11 seasons. In 2010, they had a chance to trade for Cliff Lee, the best pitcher in baseball that year. As with all trade rumors, we can never exactly know what was discussed, and who may have turned down which offer. But the Yankees had Montero and other enticing prospects at their disposal to trade for Lee … and Lee instead went to the Rangers, who rode the lefty’s dominant performance in the ALDS and ALCS to the World Series that year, knocking off the Yanks in the process. When Lee spurned New York’s advances that offseason, the Yankees went bottom-fishing instead, taking flyers on Bartolo Colon and Freddy Garcia. Amazingly, both panned out. Still, there was a sense that last season’s team needed another front-line starter to make a title run. The Yankees never got that arm, watching the trade deadline pass without any major activity, then bowing out of the playoffs for a second straight year.

You can now make it three straight years that the Yankees could really use a strong no. 2 starter to slot in behind Sabathia. But the team’s lowball bid on Yu Darvish and lack of strong interest in C.J. Wilson and Mark Buehrle point to a GM who either didn’t want to spend a ton of money on free-agent pitchers this winter, didn’t like the names that were out there, or both.

Of all the lessons Cashman has learned in the past decade, none resonate more than this: The playoffs can be random, capricious, and cruel. He might still pursue a starting pitcher via trade, sign someone like Hiroki Kuroda as a solid tier-two option, or upgrade the roster in other ways. But if he doesn’t, he can look at a team built with true stars, not retreads, one with rare upside for a Yankees club with Montero poised to improve over a 162-game season. If the Yankees do nothing else this offseason, they’d be a strong bet to get back to the playoffs, where they’d have about as good a chance as anyone of going all the way.

The New York Yankees have become more frugal than they have in years, with enough patience to make them baseball’s most unlikely story of Zen. Wonder what George would say if he could see them now.

Jonah Keri’s new book, The Extra 2%: How Wall Street Strategies Took a Major League Baseball Team from Worst to First, is a national best-seller. Follow him on Twitter at @JonahKeri.

Previously from Jonah Keri:

Will Yu Darvish End The AL East’s Grip On The Wild Card?
Who Do ‘Yu’ Think Your Are?
Who Should Sign Prince Fielder?
What Do We Really Know About Ryan Braun?

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Jonah Keri is a staff writer for Grantland. His book The Extra 2%: How Wall Street Strategies Took a Major League Baseball Team From Worst to First is a New York Times best seller. The paperback edition of his new book, Up, Up, and Away, on the history of the Montreal Expos, is now available.

Archive @ jonahkeri