You’ve Got Mail: Bill Simmons and Jonah Keri Discuss Desmond Jennings


From time to time, Grantland editor in chief Bill Simmons likes to harass his staff by e-mail, start arguments with them and prevent them from doing anything legitimately productive. Yesterday, he pulled that trick on Grantland’s lead baseball writer and resident Canadian, Jonah Keri.

The topic: Desmond Jennings.

Simmons
Jonah, I need you to climb off Andrew Friedman’s lap for a few minutes, stop feeding him grapes and answer the following question: Why did Tampa wait nearly four months to promote Desmond Jennings from Triple-A?

He’s a phenom. He’s terrifying. He’s doing things we haven’t seen since Kelly Leak was ripping up Little League fields in Southern California. In 134 at-bats since they brought him up on July 23, he’s gone .351/.439/.634 with 8 homers, 14 steals and a WAR of WTF. Sometime over the next week, Jennings could pass Carl Crawford in steals, homers and walks while also having a higher slugging percentage than Crawford’s OPS … which, by the way, makes me want to sit on a pitchfork. With apologies to Justin Verlander and Jose “I’m sure as hell not the same at home after that ESPN Mag sign-stealing story” Bautista, Jennings has been the best player in either league since Tampa brought him up. With apologies to my man Jacoby Ellsbury, Jennings has been baseball’s most exciting player and the most exciting player in any team sport save for Lionel Messi. Actually, screw that midget Messi; I’d rather watch Jennings. He’s been so ridiculous that Bill James is going to have to release another Historical Baseball Abstract just to figure out where D.J. ranks against Ruth, Cobb and Hornsby.

Normally I would be delighted that Tampa screwed up this badly and played the likes of Sam Fuld and Justin Ruggiano ahead of Willie Mays 2.0. But I have Jennings on my League of Dorks team. We were counting him on this season, but by the time Tampa called him up, our season was already in shambles. This makes me angry because, for three solid months my co-owner, Hench, and I couldn’t figure out — for the life of us — why they wouldn’t call Jennings up. So they could delay his free agency for another year? He’s already 24 years old! By the time he hits free agency, he’ll be in his 30s!!!!! And it’s not like the 2011 Rays were in rebuilding mode — they were a borderline playoff team with some genuine A-listers (Shields, Price, Longoria, Zobrist, etc.); Manny’s steroid suspension was the perfect opportunity for them to say, “Screw it, let’s give the kid a shot.” What the hell took them so long?

Here’s where you say, “They never thought Jennings would be this good.”

NOOOOOOOOOOOOOO! NOOOOOOOOOOOOO! We knew Jennings was going to be good! Keith Law ranked him as the 20th-best prospect in baseball in the preseason … one spot ahead of Michael Pineda. You know, the guy who made Seattle say in late-March, “Screw the free agency thing, this guy is ready, we’re bringing him up.” At what point can you get TOO cute? I think we’re here. Congratulations, Tampa, you delayed Desmond’s free agency for an extra year … and ruined your own season and my fantasy season in the process. I’m going to mail you the extra 2 percent of the crap I took this morning.

Keri
Bill, I’m hurt and offended that you think of me that way. Grapes are a commoner’s food. I only feed Andrew the finest medallions of Wagyu beef, drizzled with truffle oil and seasoned in unicorn’s blood. Nothing but the best for the greatest general manager in the history of organized sport. Nay, the greatest man who ever lived.

Let’s get the obvious stuff out of the way: Jennings is an absolute joy to watch, no doubt about it. Hell, if the only time you ever watched Deezy play was Sunday against the Jays, that would be reason enough to go nuts. On the very first pitch of the game, Brandon Morrow, who’s a damn good pitcher despite his mediocre record and ERA, threw a high fastball, inside edge. Jennings hammered it, a line drive that left the park faster than a Red Sox fan fires off a creative nickname at J.D. Drew. He homered again later in the game, and reached base five out of six times up. I’d argue that Curtis Granderson and Troy Tulowitzki have been a little better than Jennings in the past five weeks, but it’s close.

In related news … it’s five weeks.

From July 4 to August 11, 1990, Yankees rookie Kevin Maas hit 13 homers in 30 games, and slugged .704.

From July 25 to August 25, 1987, Red Sox rookie Sam Horn hit .346/.418/.741.

Horn’s biggest claim to fame is that his name now adorns one of the best fan forums on the web. Maas is now an assistant fry cook at a McDonald’s in Hoboken.

Simmons
That’s not fair! You didn’t have to bring Sam Horn into this! NOT FAIR! I’m still trying to unload his rookie cards on eBay. Only 2,000 more to go.

Keri
You could spend days digging up other examples of rookies who went nuts in their first month in the majors. Did Maas and Horn come with as much prospect hype as Jennings did? Fair to say, no. But prospects are tough to predict. Taking nothing away from Keith Law (who obviously knows his stuff), you cite Jennings’ no. 20 ranking as if that automatically makes him the next Musial. Here are some of Baseball America’s no. 20 prospects:

    2003 Jeremy Bonderman
    2004 Josh Barfield
    2005 Jeff Niemann
    2006 Carlos Quentin
    2007 Mike Pelfrey
    2008 Fernando Martinez
    2009 Gordon Beckham

Josh Barfield is currently the assistant to the assistant Hoboken McDonald’s fry cook, in case you were wondering.

Simmons
And Gordon Beckham was one of the guys who destroyed my 2011 League of Dorks season. Even worse, we protected him for an extra two years, so going into next season, either we have to keep him at 15 dollars, or waive him and lose $8 at the 2012 auction. People have had easier times getting rid of STDs.

Keri
Back to Jennings. He played in 109 games last year at Triple-A. You know how many homers he hit? Three. He dealt with wrist and shoulder injuries all season, and hit just .278/.362/.393. Ninety-eight percent of the time, when a team says they’re keeping a hot prospect in the minors so he can get more seasoning, they’re spouting bullshit. The Rays themselves have been too conservative with several good, young players in the past few years. But if you’re going to be a starting corner outfielder on an AL East team that fancies itself a contender, walks and defense and speed aren’t enough. The Rays needed to see evidence that Jennings could turn on a fastball and do something with it. They didn’t have that at the start of the season. Even this year, Jennings dealt with some injuries, including more wrist soreness, and a broken bone in his finger. So when Manny got pinched, they had to decide if a prospect coming off a punchless, injury-plagued season was ready to become an everyday player, while also restarting his service time clock. It was hardly a sure thing.

Still, I don’t totally disagree with you. Sam Fuld went nuts in April (not that the Rays should have expected that), so they were more than covered. Then he stopped hitting, and they didn’t have a viable replacement on the major league roster. I still think they should have brought up Brandon Guyer, the other outfielder they got in the Garza deal who’s a prospect but not as good as Jennings … and even then, they got too cute. Both in 2008 and 2010 they had a chance to make a deadline deal for an impact player who might have put them over the top. Yes, they won the AL East both times, and yes, the playoffs are hard to predict. But flags fly forever. In 2010 especially, I felt strongly they should have done whatever it took to get Cliff Lee. They didn’t. The Rangers did. Texas was a great team last year. But if Lee went to the Rays instead, it would have been Tampa Bay battling the Yankees for the right to go to the World Series.

So yes, once Jennings proved he could hit, I’d have liked to have him come up. But they waited because of service time (since Deezy was up last September — July, not June, was the Super 2 cut-off) and because of the finger injury, and likely cost themselves a couple of games in the standings. It’s unfortunate, but it wouldn’t have been enough to catch the loaded Red Sox and Yankees this year anyway.

I’m sure Friedman’s really sorry about your fantasy team, though.

Simmons
Sorry, I’m not buying that “wouldn’t have been enough to catch the loaded Red Sox and Yankees this year anyway” spin. News flash: The Red Sox and Yankees will still be loaded in 2017 or 2018 or whenever Jennings’ extra free agency year kicks in … and then, the season after that, when Jennings signs for $165 million with the Red Sox or Yankees. How many more times will Tampa get the gift of a 2-10 Red Sox start, or the Red Sox’s spending one-third of their payroll on the likes of Lackey/Drew/Crawford/Cameron/Jenks? How many more times will Tampa get the gift of the Yankees being stuck in a transition year between “our guys for the next generation and our guys from the last one,” or mangling their pitching situation to the point that Ivan Nova might start Game 2 of a playoff series? (And lord, let’s hope so.)

Keri
OK, first if all, do you know what the Rays’ record was on the day that Manny bailed? 0-6. You can talk about a 2-10 start or Boston’s pissing away money on unproductive players all you want, Bill. The bottom line is that at that time, the Rays had reason to believe that a season projected to be merely pretty good might in fact be mediocre or worse. But let’s play optimists and say the Rays wouldn’t overreact to six lousy games. Then we have to do the same for Boston. And nearly five months later, the Sox are on pace to win 100 games and fulfill the nearly universal preseason prediction that they’d be the best team in the American League. As for the Yankees, they were seen as having rotation issues, yes. But they were widely picked as the second-best team in the league, and sure enough they’re on pace for 98 wins. It’s absolutely the case that only Bartolo Colon and the Dr. Moreau character he visited could have foreseen what he’s done. But they’ve also gotten disappointing seasons out of A-Rod, Burnett, and others. They had flaws, but they were still an excellent team coming into the season, and they are one now.

Simmons
After Monday’s games, Tampa has 60 losses, New York has 52 losses and Boston has 51. Tampa plays Boston and New York 13 more times. I don’t understand why you’re callously dismissing their admittedly slim playoff hopes, or pretending that an entire Jennings season wouldn’t have made the race much more interesting. Even I’m not dumb enough to think Jennings would be sitting on a 1.13 OPS, 55 steals and 30 homers had they brought him up in April, but even a reasonably good four months that included one hot streak — let’s say .290/.370/.490 with 45 steals and some sterling defense in left field — would have been worth three or four extra wins, right? Besides, this was ridiculous as it was happening! I mean, Jennings finished with nearly 1,000 Triple-A at-bats, which was great news if Tampa’s goal was to eventually inspire Bull Durham II.

Keri
Eight games in the loss column are a lot to make up, let alone in a month. On one hand, 13 games against the Yanks and Sox give the Rays a chance to kick ass in head-to-head play and get themselves right back in it. On the other hand, those are the two best teams in the league, so those are very tough games. (They also have six games left against a very good Texas team.) I absolutely buy the old saying that to be the best you have to beat the best. But this Rays team is not the best. Shortstop is a disaster, B.J. Upton’s had a lousy year by his standards, Evan Longoria’s been BABIP’d to death, catcher’s not pretty, nearly everyone in the bullpen outside of Farnsworth and maybe Peralta have been heinous, etc. Anything can happen in sports, of course. But this was not a great team at any point. I just don’t think — and more important, they didn’t think — this was their year.

Simmons
Please, you act like this was such a disastrous Tampa season. Good luck getting 700 innings, a 3.20 ERA and 600 Ks out of Hellickson, Price and Shields again … not to mention 27 shocking, decent starts (and counting) from Jeff Niemann and Alex Cobb, or even a ridiculously competent closer year from the one and only Kyle Farnsworth, or everything Matt Joyce and Casey Kotchman did, or Ben Zobrist’s second sneaky-ridiculous saber season. I’m not buying it. Although I like this year’s excuse for Longoria not living up to the “Next Big Superstar” hype again; now he was BABIP’d to death? Do we have any suspects yet? Is this going to be a Law and Order episode? And by the way, I’m sorry Bud Selig put a gun to Tampa’s head from April through July and prevented the Rays from trading Upton for additional help to open center field for Jennings.

Keri
I think we just fundamentally disagree on the meaning of those 35 games for Jennings. You say “.290/.370/.490 with 45 steals and some sterling defense in left field” like it’s a snap. That’s an elite player given where league-wide offense is right now and the pitcher’s park he plays in. Manny retired on April 8. Based on what Jennings had shown to that point, there was no way in hell anyone could reasonably project anything close to that kind of dominance by Jennings at that point.

But this assumes that all baseball decisions are linear, with one neat and clean answer to every question. Maybe that’s the way it is if you’re a Sox or Yanks fan. But it just isn’t that way for the Rays.

Simmons
(Oh, here we go. Lemme get my violin. Hold on …)

Keri
The Rays deal in odds and probabilities. It’s possible that Jennings could have terrorized the league all season. It’s possible that the Rays could have counted on dominant performances from the likes of Farnsworth and Kotchman. It’s possible that in addition to all that (we’ve established that would merely be enough to put the Rays within some kind of striking distance), Reid Brignac and Sean Rodriguez would have hit and John Jaso would have matched his 2010 performance and Longoria would have slayed the luck dragons and Upton would have finally fulfilled the superstar potential we all think he has but probably doesn’t exist. It’s possible they would have overcome their big offseason splurge being a total bust. It’s possible that all of those things would have fallen into place, that they would have won 100 games and banked their third division title in four years. Possible. But not likely.

So they played the percentages, waited for Jennings to prove himself in the minors first, and here we are.

Simmons
OK. But if you’re building a relationship with a potential star for the long haul, someone who can hopefully be tricked into signing one of those secretly evil Longoria-like extensions (in which a young player grabs money/security upfront but yields upside on the back end) someday soon, don’t you want to do right by that guy? If I’m Jennings and I’m looking at a FOURTH straight year in Triple-A, and I’m looking at the box score and seeing the likes of Ruggiano and Fuld playing ahead of me, here’s my mind-set: “I hate the Tampa Bay Rays.” That mind-set would affect my day-to-day approach, my spirits, my feelings about remaining in Tampa for as long as possible, you name it. Why risk jeopardizing your relationship with someone who, again, was considered one of the top prospects in baseball? And why risk pissing off your small base of fans who are already pissed off that they’re rooting for a team that spends one-fourth as much money as two other teams in its division? Isn’t the goodwill of your understanding the Rays’ fan base more important than anything?

What happened was a classic example of an extremely smart baseball team making a decision based on a variety of extremely logical assumptions— the biggest one being, “If we play this right, we get an extra year of Desmond Jennings!” — and ignoring some of the harder-to-measure human elements that accompanied such a decision. Yeah, you get an “extra year of Desmond Jennings” … but that “extra year” could have been this season, so it’s all relative. By the time he brought him up, it was too late. On the bright side, you have an outside chance of getting invited to Deezy’s 30th birthday party when you’re working on An Extra Extra 2 Percent: How Desmond Jennings Became An American Icon in 2017.

(By the way, am I allowed to called Jennings “Deezy” or is this privilege only extended to black people and Canadians?)

Keri
You’re exaggerating Jennings’ Triple-A time. He’d played a total of 140 games there coming into this season. Again, I don’t disagree that he was ready before they actually called him up. I do think there’s value in trying to make your prospects happy. I’ve interviewed players before who have told me how pissed they were that they’d been held back for service-time reasons.

But this wasn’t exactly the biggest miscarriage of justice in human history, either. He hit three homers last year, Bill. You’re basing your argument on after-the-fact assumptions. You say good luck getting 700 killer innings out of Price, Shields and Hellickson, a great season from Farnsworth, etc. But they had no way of knowing, on April 8, that all that would occur. And you’ve said yourself that Jennings at the very high end might have been worth three or four more wins than other left fielders (on top of his current contributions) if they’d played him all season (which, again, is an extremely optimistic scenario, but OK). Even after all those post-hoc analyses and perfect-world scenarios, they’re still four or five back of New York in the loss column with a month to play.

Simmons
But Jonah, you keep skipping over the part that there was blood in the water in April! The Red Sox flopped out of the gate. The Yankees were dealing with Phil Hughes’ dead arm, the Posada/Jeter aging issues and the disturbing fact that they were relying so heavily on Bartolo’s new and improved stem cells. On the morning of April 16, New York was 7-5, Tampa was 5-8 and Boston was 2-10. On the morning of May 7, New York was 18-12, Tampa was 18-14 and Boston was 14-18. Even on the morning of June 2, right after Sam Fuld’s historic 28-game stretch from April 28 through May 31 in which he finished .135/.164/.217 over 112 plate appearances, New York was 31-23, Boston was 30-26 and Tampa was 29-26. How does Jennings not get called up at that point? I always thought the point was, you know, to try to win. By the way, we’re ignoring the bigger issue: Any rule that discourages playoff contenders from promoting exciting rookies in Triple-A needs to be changed as fast as humanly possible.

Keri
So now we’re at June 2 being the obvious date for Jennings to get called up? He played his first game with the Rays seven weeks after that. In the interim, he hurt his wrist (again) and cracked his finger. But let’s say we’d have assumed he’d stay healthy. That’s seven weeks of extra Jennings. Even in a superoptimistic scenario, you’re getting two more wins from him vs. other left fielders over seven weeks.

As a fan of good baseball, and of teams showing not only smarts, but balls, I’d have loved to see Deezy play all season (my friend R.J. Anderson, who writes for Baseball Prospectus and chats with me 87 times a day about the Rays, calls him Deezy — you’re welcome to use it). As someone who over the course of writing a book about this team became a fan, I’d love to see a more compelling race. But from an analytical standpoint, this was the right play.

There’s no reason to lament that great seasons by a few players have been wasted. Deezy will be there on Opening Day next year, Matt Moore (who’s arguably a better prospect than Jennings or Hellickson ever was) will join the rotation at some point, they’ll upgrade their offense by trading Shields or Niemann or Davis or Cobb, and they’ll have a better chance to win next year than they did in 2011. It’d be wonderful to be able to go balls-out every year, doing everything you can to win the division. But baseball isn’t set up that way. Least of all for AL East teams outside New York and Boston. You pick your spots, then go for it.

This wasn’t that year, that’s all.

Simmons
You must be a blast at the poker tables. We’ll never agree on this Jennings thing. Alas, there’s good news — because Tampa brought Jennings up after the All Star break, we get to protect him in the League of Dorks through 2015 instead of 2014. I know you’re fired up about that, right?

Keri
You’re the guy who goes all-in with rags. I’m the guy who lets the game come to him.


Bill Simmons is the Editor in Chief of Grantland, the host of the BS Report and the author of the recent New York Times no. 1 best-seller The Book of Basketball. Follow him on Twitter and check out his new home on Facebook.

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.


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Filed Under: Jonah Keri, MLB, Tampa Bay Rays

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Bill Simmons is the editor-in-chief of Grantland and the author of the New York Times no. 1 best seller The Book of Basketball. For every Simmons column and podcast, log on to Grantland.

Archive @ BillSimmons