The long-term deals signed last winter have turned into one of the ugliest in recent memory, from the teams' perspectives.
If you look back at the biggest multi-year contracts signed by free agents every offseason, the rate of teams at some point wishing they could get out of the deal tends to be high. On the most basic level, there’s simply a lot of room for a nine-figure investment in a baseball player to go wrong, particularly when the player is usually on the wrong side of 30 years old and coming off a stretch of good performance that makes for a natural regression candidate. Beyond that, the notion of a “winner’s curse” is at work, in that any team bidding enough to secure a high-end free agent likely did so by paying a premium. And, of course, players sign deals when they're in their prime. They end them when they're old, but still getting paid like they're not.
None of which is to suggest that handing out $100 million-plus deals to free agents is always a bad idea, but rather that for the contract to be a good idea the team has to get tremendous value in the early years. There’s a tacit understanding that, for instance, a six-year, $150 million signing will not provide the team with as much value in Year 5 and Year 6 as it does in Year 1 and Year 2, but the team lives with the later years of the contract in order to get the early years. Another way of looking at it is that, if things don’t go well in those early years of a big long-term contract, the whole signing may turn very, very ugly.
Reimagining the trade deadline with just one small difference.
Consider this scenario: On July 1 a butterfly flaps its wings, which causes Red Sox president of baseball operations Dave Dombrowski to scratch his nose two weeks later, briefly postponing a scheduled phone call with Padres general manager A.J. Preller. In the meantime, Josh Byrnes, senior vice president of baseball operations for the Dodgers, calls Preller for a casual pre-deadline chat . . . so, how are the kids? Wait, do you have kids? Is Drew Pomeranz available? Dombrowski calls Preller, but it’s too late—by the time he gets through, LA’s cavalry of current and former GMs have all talked to Preller. Pomeranz is a Dodger, and the world is changed forever.
It’s a silly scenario, sure, but it’s fun to think about how much the trade deadline could have changed if just a single move had gone another way. The deadline—and the weeks preceding it—consists of many (many!) discrete trades, all interesting in various ways, even in isolation. But they’re all connected, too, and it’s always more entertaining to imagine what could have been rather than what is, at least after we’ve already analyzed what is to death. How would the baseball world have turned out different if Josh Byrnes beat Dave Dombrowski to A.J. Preller’s smart phone?
Double-switching makes for a very odd end-game in Cincinnati, Andrew Benintendi debuts with amazing hair, and David Price goes an inning too long.
The Tuesday Takeaway
The Reds entered the bottom of the eighth inning down 5-4 to the Cardinals. Of course, some things happened before that, with the most noteworthy including Adam Wainwright’s first home run since 2012
On Clay Buchholz, potential hero of the eighth month.
It’s the second of August, the Boxing Day of baseball. The buyers have bought, the sellers have sold, the fans have gnashed and fist-pumped. The players have been given their hugs and their plane tickets, published their thank yous on Twitter and the local paper, the various power rankings have been revisited and renumbered. Names have been tested, sounded out the way preteen girls don the last names of teenage heartthrobs. The games continue, even grow in importance, but there’s a psychological lull, like a racetrack straightaway.
Background: Benintendi wasn’t a complete unknown coming out of high school, but he wasn’t taken too seriously as a draft prospect in 2013 (though the Reds did pop him in the 31st round), and he honored his commitment to the University of Arkansas. After a solid but certainly not spectacular freshman campaign, Benintendi shined in 2015, putting up monster numbers in the loaded SEC conference and establishing himself as one of the best collegiate bats in the country. After Boston scooped him up with the seventh pick in the draft, he destroyed pitching at both of his professional stops (Lowell and Greenville) and earned a trip to High-A Salem to start 2016. After beating the crap out of that pitching, Benintendi was hitting .295/.357/.515 in Double-A Portland, and now will get a chance to maim pitching at the highest level.
The Red Sox signed David Price to make, roughly, 210 starts for them. The first tenth have not gone smoothly, but the next nine-tenths remain an open question.
Game 81 is long past, All-Star Week has come and gone, a handful of teams are admitting defeat with sell-offs this week, and pretty much every sample we look at feels like it's of sufficient size. We are deep into the season, which means that many deals that had fans starry-eyed in December are now leaving them wondering what went wrong in the summer.
Jeremy Hellickson aces his audition, the White Sox get to the Cubs' bullpen, and Dave Dombrowski has made so many trades that they're starting to overlap in a kind of baseball version of the grandfather paradox.
History tells us the story of two lopsided trades, but History ignores some nuance--and some lessons for this trade deadline.
There are lots of cautionary tales about trading prospects for pitchers in the heat of a pennant race. Some belong specifically to certain fan bases or regions; most also belong specifically to one or another generation. There’s the deal that sent Derek Lowe and Jason Varitek to the Red Sox in exchange for Heathcliff Slocumb, and the one that sent Grady Sizemore, Cliff Lee, and Brandon Phillips to the Indians in exchange for Bartolo Colon. More recently, there was Scott Kazmir for Victor Zambrano, and more recently still, there was Wilson Ramos for Matt Capps. There are tons of these, and because of that possessiveness each fan base and generation feels toward its favorites, you’re probably wondering why your personal highlight wasn’t among the ones I just rattled off.
I want to talk, though, about two of the highest-profile versions of this fable in history. As it happened, they occurred just three years apart, and almost 30 years ago. They’re the ones you probably conjured quickest, when you read the first sentence, even if they’re not the ones with which you identify most closely. Here they are: