A dumbfounding night in the ‘Dumbleavy Era’

Tweet, tweet! The mailbag flies again

‘Now I Can Die In Peace’ — The Manny Signing

With an updated edition of "Now I Can Die In Peace" hitting the bookshelves, it's time to look back at the Red Sox courtship of Manny Ramirez. Bill Simmons

Editor’s note: The following is adapted from the new edition of Bill Simmons’s book,
Now I Can Die in Peace: How The Sports Guy Found Salvation Thanks to the World Champion (Twice!) Red Sox,”
copyright (c) 2009 by Bill Simmons. Excerpted by permission of ESPN Books. All rights reserved. No part of this excerpt may be reproduced or reprinted without permission in writing from the publisher. The following selection is from a column that was originally published on December 18, 2000.

“Outside The Lines” — The Manny Signing

Now I Can Die in Peace by Bill Simmons

I thought my winter peaked when Manny Ramirez signed with the Red Sox … and then I watched ESPN’s “Outside The Lines” documentary where they followed Manny’s agent around for two months. In case you missed it, here’s a running account of the most captivating Boston-related TV show in recent memory.

October 23: Jeff Moorad (Manny’s agent) and Scott Parker (Moorad’s associate) are riding around Cleveland in a limo. Moorad looks like a cross between Dan Fouts and Rob Reiner and has a bubbly, “Hey, I’m on TV!” glow about him. You have to question the motives of any agent who allows cameras to follow him for a pivotal six-week period of his career (he’s obviously seen “Jerry Maguire” one too many times). Anyway, Moorad tells the camera that he hopes to make Manny the highest-paid player in the game. Somewhere A-Rod giggles.179

That same day: After finishing an off-camera meeting with Tribe GM John Hart, Moorad calls Manny to recount the details of the negotiation. You just know Manny’s playing Nintendo or watching the Flintstones. Where’s the Manny-cam?

November 2: Moorad tells Hart by phone that he wants $200 million over 10 years, adding, “You have to swallow hard on something if you want the guy.” That choice of words narrowly edged the runner-up choice, “You’re gonna have to bend over and hold onto your ankles if you want the guy.”

November 9: Yankees GM Brian Cashman calls Moorad to express a “strong interest” in Manny, adding that they’re considering a few other big-name guys (like Mike Mussina) and that “whoever decides they want to be a Yankee the most, first, obviously is gonna take us in the direction we want to go.” Moorad responds with a hint of indignation: “Well that doesn’t sound like a real compelling reaching-out to Manny Ramirez.” Apparently grammar isn’t a major priority when you’re a big-time agent. At least his power play scares Cashman, who hems and haws before rushing off the phone. “Now we’ve got our 300-pound gorilla,” Moorad says, dollar signs dancing in his head.

That same day: Moorad eavesdrops on a conference call between Cleveland beat writers and [Cleveland GM John] Hart, who says that Moorad “made it very clear that this is going to be an economically-driven contract,” prompting Moorad to nod with a “You’re f—— right” look. That was fun. Later Moorad calls another associate and admits that he doesn’t know where the Indians are headed, wondering why they’re “almost daring us to go on the market.” Why is it so much fun to watch sports agents squirm?

November 11: The Indians fax an offer for $119 million over seven years. Moorad calls Hart and “respectfully” declines. All we’re missing at this point is a follow-up scene with Moorad driving in the car and belting out the words to “Freefallin'” by Tom Petty.

November 13: A Seattle meeting features Moorad (who used the Miami Vice beard trimmer for the El DeBarge180 look); ancient Mariners GM Pat Gillick (wearing a bright red sweater and looking ready for a bingo game); and Mariners president Chuck Armstrong (I’m pretty sure that’s a stage name). Moorad relays a special message from Manny (“Tell them to put up the money and I’m there!”), then giggles like a hyena. Mesmerizingly awkward.181 When Gillick asks if Manny would consider coming to Seattle, Moorad mentions Manny’s concerns about Safeco Field and wonders if they would move in the fences for him, prompting Armstrong to give one of those stammering, “Um, can I borrow your towel, my car just hit a water buffalo?” answers like John Koktostin in “Fletch.”182 Buh-bye, Seattle.

With free shipping on Amazon.com, you can buy the expanded edition of Bill Simmons’s New York Times best-selling book, Now I Can Die in Peace: How the Sports Guy Found Salvation Thanks to the World Champion (Twice!) Red Sox, in paperback for just $10.88, updated through 2009 with new takes on Pedro, Big Papi, Manny and more.
Buy at Barnes & Noble
Buy at Borders

November 14: By phone, Moorad updates Manny on his offers, tells him that the process won’t get going until the winter meetings, then adds this tidbit: “I told Dan Duquette that, listen, Pedro is a good friend of yours, that your preference was to stay in the American League. I also like the fact that there’s a significant Latino population in Boston … you know, when Pedro pitches up there, they have the entire ballpark filled with Dominican flags.” Apparently, Jeff hasn’t heard about the recent ticket hikes at Fenway; the only Dominican who can afford to go to Red Sox games anymore is Pedro.

(By the way, maybe it’s just me, but Moorad sounds more and more like Fouts every minute. I keep waiting for him to say things like, “One of the keys to this negotiation will be which team offers the most money” and, “Any time somebody offers you $160 million, that’s more money than $119 million.”)

December 1: One day after Mussina signs with the Yankees, Red Sox assistant GM Lee Thomas calls Moorad in a quivering voice and asks, “Dan wanted me to ask you and, to kinda put it bluntly, would there be any need for us to get involved with Ramirez? Are we out of the box already or is there any chance for us to talk about him?”

(Translation: “We screwed up with Mussina, we need Manny to save face, money is no object whatsoever, and we’re so embarrassed about this whole thing that my boss didn’t even have the balls to call you, he had me do it. Any interest on your end? Any at all?”)183

December 5: Duquette and Thomas arrive at Moorad’s hotel room in Miami to meet with Team Manny. After everyone sits down, Duke hands a sheet of statistics to Manny that shows “how we think you can really help the Red Sox,” which Manny examines like somebody checking out an unexpected subpoena.184 Not a good idea. They should have gone with Plan B: A $50 bill and the latest Marc Anthony CD.

(Please note that, for the duration of this show, Duquette wields the on-camera charisma of a seven-state serial killer being interviewed on an HBO “America Undercover” special. At every point in every conversation, you keep waiting for him to spring forward and jam a pencil into Moorad’s neck. You know it’s killing him that Moorad made him pitch that “Come to the Red Sox” spiel to Manny in front of ESPN’s cameras. Comedy galore.)185

Duke and Manny then combine for one of the most awkward exchanges ever captured in television history:

    Duke [monotone]: The fans in Boston appreciate your unique skill and your ability to hit.

    Manny [sounding like Chico Escuela]: I’m one of those guys that don’t talk a lot you know and just go and try to play the game and that’s it you know.

    Duke: Yeah. [Stifling silence] You’ve always been, uh, quiet and business-like and ready … [forced smile.]

    Manny: That’s the only thing you could do … you know, just work and see what happens. [Dead silence.]

    Duke: Sometimes I pick up prostitutes, bring them back to my apartment and strangle them to death.

    (I made that last part up, sorry about that. Couldn’t resist.)

    And then the phone rings … it’s No-mahhhhh! Manny looks and sounds like a 13-year-old girl getting called for her first date. Unfortunately we can’t hear what Nomar is saying on the line, but still …

    Manny [talking into phone, heavy Chico Escuela effect here]: Eh-lo?… Hey, wass goin’ on, man?… Everything’s fine so far… Yeah, everything’s cool… Yeah, well, joo know… I hope this will work out… Yeah, I like joo guys, joo know…

    (Another scene that simply can’t be done justice in print. Oh, well.)

December 6: Boston’s offer: Eight years, $136 million. Cleveland counters with five years and $100 million. Narrating the show, Bob Ley ominously says, “The numbers can only go up. The question is, how far?” Hmmmm.

December 9: One day after Duquette arrives in Moorad’s California office — and let the record show that there was a “Jerry Maguire” poster in the lobby — Moorad pushes Boston to increase its offer, forcing Duke to call Red Sox CEO John Harrington to seek approval for the extra funds.

(Now there’s a phone call that should been broadcast on live TV: “Hey, Mr. McDonough? It’s Duke. Is Mr. Harrington there? Can you roll over and wake him up?)186

Moorad tells an associate, “We’re close,” but that doesn’t stop him from calling Hart for leverage. Hart explains that he’s trying to get Cleveland’s owners to accept eight years and adds, “I made it clear that if all things were equal or close to being equal, you’re going to send Manny here.” Moorad replies that Manny’s No. 1 request was a competitive deal in Cleveland. He doesn’t elaborate on Manny’s No. 2 request, which was probably something like, “I want a never-ending supply of mint-flavored toothpicks!”187

December 10: Moorad arrives in Dallas for the winter meetings and updates Manny by phone, explaining that things should be settled soon. Cleveland finally raised its offer and went to eight years, but some money was deferred. Being a money-grubbing whore-er, talented agent, Moorad will use that offer to squeeze the Red Sox. Riveting stuff.

Later that night: Cut to Moorad and Duke negotiating in a hotel room. Duke looks like Nicholson at the end of “The Shining”; he’s only missing the five o’clock shadow, the typewriter and the axe. They have the following exchange:

    Duke [monotone voice, glazed expression, looking like an airplane crash survivor]: Our-our preference would be … to defer … two (million) … out of each of the years.

    Moorad: I know that at one point you proposed those without the deferrals.

    Duke: Um … [long pause, psychotic look, weight of Red Sox Nation on his shoulders] … I would say that, um … I would say that we would just prefer it, um … on a, uh, cash flow basis.

    Moorad: So you’re talking years nine and 10.

    Duke [staring straight ahead]: Correct.

    Moorad: So you’ll do the 20 (million per year) if you can defer two (million) each year. Correct?

    Duke [practically flat-lining]: Yes.

    Moorad: Both club options?

    Duke: Yes, yes.

    Moorad: I don’t think I have anything to ask for … other than more money!

    [Moorad unleashes a loud, grating laugh as Duke fantasizes about slitting his throat.]

With Boston’s offer in hand, Moorad scurries back to the Indians even after telling Duquette, “My gut is that (Manny) chooses Boston.” The Indians crunch some numbers and Moorad makes plans to fly Ramirez to Dallas for a final decision.

December 11: Moorad awakens to a morning phone call from Manny, who has a surprise announcement: He’s ready to accept Boston’s offer, but only if they agree to hire (Cleveland clubhouse attendant) Frankie Mancini as well. There’s comedy, there’s high comedy, there’s transcendent comedy, and then there’s the moment when Moorad relays his request to his associates by phone and explains, “Frankie Mancini … he sets up the pitching machine for him … [realizes how ridiculous this is, starts giggling hysterically] … are you kidding me??? [more giggles] That’s why he’s Manny.”

(There are a million different reasons why we’ll adore Manny over the next decade, but I can’t imagine anything topping, “I’ll move to Boston, but I have one last request — the guy who sets up the pitching machine for me gets to come, too.”188 Manny seems like one of those media-hyped “quirky characters” who really is quirky. The possibilities for the next eight years are limitless. In a good way. I keep telling myself this.)

Later that day: Mancini doesn’t want to leave Cleveland, but Ramirez still accepts Boston’s offer. GO SOX! Cut to Moorad and Duquette hammering out the final numbers, with a nodding Duquette looking like he just fought off another electroshock treatment. My only regret here is that I’m not talented enough to describe how freaking strange and disoriented the Duke seemed for this entire show. He should have been strapped to a stretcher and forced to wear a triple-pronged metal mask like Hannibal Lecter. Anyway, Moorad calls Manny to give him the good news, then puts Duke on the phone for the final dose of comedy:

Duke [monotone, strange smile]: Hi Manny, how are you? … Congratulations … we’re so happy to have you with us, I think it’s gonna be great. You’re gonna love Boston, the fans are gonna love you, and you’re gonna be able to get recognized among he great hitters in the history of the franchise. We’re so excited to have you. And you what the good news is? You don’t have to hit against Pedro!” [Loud, excited, startling out-of-character laugh.]

The end.

The question remains: Will we ever be able to take Duquette seriously again?189 Is he always like that? Did the cameras make him uncomfortable? Is part of his negotiating process to make other people feel uneasy? Does he remind anyone else of Johnny Depp afer the explosion in “The Astronaut’s Wife”? Did anyone else see “The Astronaut’s Wife”? Why does all the acrimony from the first six years of the Duquette Era suddenly make sense when you witness this man in action? I mean, seriously … should a man lacking any discernable social skills be allowed to run a major league baseball team?

Let’s save those questions for after the holidays. If you didn’t realize how close the Sox came to losing out on the premier righthanded slugger in baseball, check out the replay of this show on Christmas Day. My preference is, um … that … you watch … the show … just for the, um … Duquette stuff … because it’s, um … it’s that phenomenal … and I really, um, think it’s um, a special show … and, um, Merry, um Christmas …


179 The following winter, A-Rod’s Texas deal dwarfed Manny’s deal by two extra years and $92 million. Two winters after that, the two players were nearly traded for one another in the first Double Contract Dump trade. You have to love baseball.

180 I thought about changing this to the “Jerry Bruckheimer look,” just to make it a little more current … but there’s something funny about seeing El DeBarge in a Red Sox book. Even when I wrote that one, that reference was dated. Now it’s almost prehistoric.

181 When he watches a tape of this show now, Moorad must feel like one of those Real World castmates watching footage from that drunken threesome they couldn’t quite remember in Mexico. By the way, Moorad ended up leaving the sports agent business and signing a deal to run the Arizona Diamondbacks in 2004.

182 Huge internal debate on how to spell that one — was it Koktostin, Cocktoasten, Kocktostine … I mean, that could go 20 different ways, right?

183 The “Mussina or Manny?” debate was the No. 1 sports radio topic in Boston that winter, with the Sox targeting Mussina and losing out because Duquuette was outworked by Cashman and the Yanks. For some insane reason, the Sox decided to raise ticket prices at the same time, forcing Duquette to either land Manny or risk being drawn-and-quartered in Kenmore Square. This explains Boston’s sudden urgency.

184 Funniest moment in the whole show, by the way.

185 Duquette was a dead ringer for Sam Neill in “Omen III: The Final Conflict” to the point that I called him Damien Duke on my old website.

186 That was an inside Boston joke: John Harrington was the longtime Red Sox CEO; Will McDonough was the ledgendary Globe columnist who consistently defended certain players in the Boston scene (Harrington, Red Auerbach, Bill Parcells) and ripped others (Roger Clemens, Mo Vaughn, the late Reggie Lewis, Bob Kraft) before his death in 2003. You could always count on him to defend Harrington, no matter what the circumstances were, even if there was videotape of Harrington tossing babies off the Green Monster. McDonough’s son, Sean, the longtime broadcaster for the Red Sox, later confessed to me that this was his favorite joke in the whole column. Although he winced when he read it.

187 This is one of those shows where you know the ending, but every time the Yanks and Indians get involved, it’s still frightening for some reason — like every time the Nazis take a 4-0 lead in Victory.

188 This is actually now my second-favorite Manny story of all time. The first? When his mother revealed that Manny was breast-fed until he was four years old. Never has one sentence revealed so much.

189 Not only was the Duke fired 14 months later, he hasn’t worked in baseball since. And here’s the weird thing: He still lives in Massachusetts, attends Red Sox games, even calls to local radio shows. If Theo Epstein ever disappears without a trace, here’s your No. 1 suspect. By the way, after the 2001 season (Duquette’s last with the team), I wrote that he “failed spectacularly” and “even Sofia Coppola’s casting in ‘The Godfather III’ wasn’t this big of a misfire.” I also handed out 50 quotes from The Godfather as awards for the 2001 season, with Duquette receiving five in all, including “What guarantees can I give you, Mike? I am the hunted one. I missed my chance … ” “Dammit, if I had a wartime consigliere, a Sicilian, I wouldn’t be in this shape! Pop had Genco, look what I got!” … and “Barzini’s dead. So is Philip Tattaglia. Moe Greene. Scracci. Cunio. Today I settled all family business. So don’t tell me you’re innocent. Admit what you did. Don’t be afraid. Come on, you think I’d make my sister a widow?”

Bill Simmons is a columnist for Page 2 and ESPN The Magazine. For every Simmons column, as well as podcasts, videos, favorite links and more, check out the revamped Sports Guy’s World.

Filed Under: Bill Simmons, People, Series, Simmons, Sports, The Sports Guy

Bill Simmons is the founding editor of Grantland and the author of the New York Times no. 1 best seller The Book of Basketball. For every Simmons column and podcast, click here.

Archive @ BillSimmons