WHAT IF…the Houston Astros used the first pick of the 1992 draft and selected Derek Jeter?
T. Sean Shannon is an Emmy award winner, having written for Saturday Night Live for 8 years, 3 as writing supervisor. He is a life-long Houston Astros fan and answers the question.
1992 – 1995 - MINOR LEAGUES –
The Astros have the first pick of the 1992 draft and select 18 year-old Derek Jeter. Derek is assigned to the rookie ball and quickly climbs through the minor leagues with both his stick and his glove, quickly establishing himself as a leader.
Derek joins the killer B’s of Jeff Bagwell, Craig Biggio, Sean Berry and Derek Bell. Biggio at 30 is the oldest of the bunch and especially hard on rookies. With the press hyping the new, hot-shot, shortstop, Biggio focuses most of his negative attention towards Derek. But in typical Jeter fashion, he’s able to handle it and by midseason he wins Biggio’s respect. Biggio leaves Jeter alone and starts terrorizing Bobby Abreu.
Derek has a great year at the plate, taking full advantage of the spacious dome hitting .422 at home and .359 overall and wins the N.L. batting title, sadly the Astros finish 2 games behind the Cardinals in the N.L. Central.
Apologies to Todd Hollandsworth, but you no longer win the N.L. Rookie of the Year, it’s given unanimously to Derek Jeter.
Larry Dierker takes over as manager and everything falls in place and the Astros easily win the National League Central.
When the playoffs come around Derek Jeter sets the tone. Over his career, Jeter’s batting .500 against Greg Maddux and .350 against Tom Glavine so the Astros breeze past the Braves,sweep the Marlins and beat Cleveland and the Astros franchise win their first World Series!!!
During the off-season, Derek holds a black tie charity event at the Rice Hotel and wants to hire a comedian and someone gives him my name. I go up at the end of the night and have to follow the bachelor auction. The crowd is drunk and rowdy but I shut down a couple hecklers, take control of the room and end up killing for 45 minutes. After I get paid, I’m thinking about cutting out but Derek asks me to hang out. After the party dies down we spend the rest of the night with him quizzing me about my set. He wants to know how I think up jokes and how I was able to shut down the hecklers. I tell him it’s hard to explain, I was just in the zone. He smiles and knows exactly what I mean. We decide there’s a lot of similarities between baseball players and comedians.
The next day he stops by the house for dinner. My wife, Kitty is a trained chef, and fixes him Chicken Fried Steak. He can’t stop talking about how it’s the best thing he’s ever eaten. I say “This is amazing, but her specialty is breakfast.” I don’t even remember saying it till the next morning at 9 when Derek’s BANGING on the door.
By the end of breakfast Derek convinces us to become his partner in the restaurant biz. Derek wants to call it Number 2 until I convince him no one wants to eat food at a place called number 2. We name the restaurant The 713, after the local area code and it’s an immediate hit and gets 2 Michelin stars, which I guess is a big deal.
In the fall of ’97 I get hired at Saturday Night Live and Derek takes my wife and I to Galveston for a celebratory weekend.
Astros win their second World Series and Derek Jeter continues to use the confines of the Astrodome to his advantage. Derek ends up hitting .391 and winning his first MVP award, just nudging out Sosa and McGwire. I have an MVP year too, in my rookie year writing for Saturday Night Live, I tie for third on the staff with most sketches on the air.
Jeter starts his first All-Star game in Coors Field in Denver and we have a blast. Monday, we sat around talking to Cal Ripken Jr., Barry Bonds, and Tony Gwynn. Later, at the hotel bar, I some how piss off Gary Sheffield. I’m not even sure what happened, but he’s staring bullets at me the whole night.
The next day I’m shagging balls during batting practice, when a ball zips by my head. I can hear the whoosh as it buzzes by my ear. I can’t prove it, but I know it was Sheffield.
After the game, I’m in the hotel lobby waiting for Sheffield. Derek can tell I’m mad.
“T. Sean, you have every right to be pissed off and I know you want to fight Sheffield but as a favor to me, I’m asking you to let it go. Plus, Sheffield’s a big dude and I’m pretty sure he’ll beat the shit out of you.”
“As a favor to you, I’ll let it go.”
The next day I sign up for Krav Maga lessons. Two months later I’m a blue belt, which takes most people four years to earn.
The Astros are kicking ass in baseball, just like I’m kicking ass at Saturday Night Live. Derek is a very funny guy and sometime he phones me with ideas. I came up with the idea for Jimmy Fallon’s character Nick Burns – Your Company’s Computer guy based on stories Derek told me about the Astros computer guy.
The All-Star game is in Fenway and Derek hits for the cycle and makes and unassisted triple play to help the National League win 7 - 1. Derek is the obvious choice as MVP.
During warm ups, I’m hanging out behind the fence under the bleachers. Gary Sheffield said I was back their hiding, which is bullshit. I didn’t even know Gary made the team; last I looked he was batting .250. Plus I’m a first degree black belt in Krav Maga so I’m definitely not dodging him. I’ve fought a fifth degree black belt at my dojo and it wasn’t even close – I beat the crap out of her.
Anyway, I’m hanging under the bleachers and a golf cart rolls up carrying Ted Williams. Ted notices my t-shirt from the Golden Bosun Tavern.
“Golden Bosun Tavern? Where’d you get that shirt?” Ted asks.
“I bought it when I was down fly fishing on the Christmas Islands.”
“I like you, kid,” and he sticks out his hand, “I’m Ted Williams”.
We spend the next hour hanging out. Cut to - 2 weeks later, I’m in Florida and Ted takes me on his boat and drives to Cuba. We go fly fishing with Fidel Castro during the day and that night we smoke cigars and watch baseball. On the boat ride back to Florida, Ted and I laugh about how shitty Castro is at fly-fishing.
In the last baseball game ever to be played in the Astrodome, the Astros become World Champions in dramatic fashion when Derek Jeter hits a 2 run walk-off home run in the bottom of the ninth off Yankee reliever, Mariano Rivera. Not a bad way for Derek Jeter to enter the free agent market.
It’s 2 weeks after the World Series and I’m at SNL and Lorne invites me to party on a yacht circling Manhattan. We get there and there’s only about 20 other guest, but it’s a who’s who of New York; Mayor Giuliani, Billy Crystal, Jay-Z, Chef Mario Batali, Robert DeNiro, Donald Trump, Lou Reed…
So Lorne and I are at the front of the yacht and the ship goes through a fog bank and when we come out of it, George Steinbrenner is standing in front of us with a briefcase handcuffed to his arm.
“Hi, George. I’d like you to meet T. Sean Shannon. T. Sean, this is Mr. Steinbrenner.”
Steinbrenner uncuffs his arm, then opens the briefcase to reveal it’s full of stacks of 100 dollar bills. “There’s 250,000 dollars in here.” He closes it back up and handcuffs the briefcase to my wrist and gives me the key.
“A small gift so you’ll convince Derek Jeter to sign with the Yankees.”
“I’m flattered that you think I have that much influence on Derek, but he’s his own man and nobody can tell him what to do.”
“T. Sean. Can I call you T. Sean?”
“I am my own man, T. Sean and like Derek Jeter, no one can tell me what to do. That said, when I have an important, life-changing decision to make, I always seek counsel from my best friend.”
“Mr. Steinbrenner, we hang out, but I wouldn’t say we were best friend.”
“Oh please, every interview I read it’s like ‘my buddy T. Sean said this, my buddy T. Sean said that, if my friend T. Sean was here... ‘ It’s obvious you’re best friends.”
“I never put a label on it, but yes I guess you could say Derek Jeter and I are best friends, but his parents are the biggest influence.”
“And they love you,” exclaims Steinbrenner. “I read in an interview you taught his mom how to make red beans in rice.”
“Mom said that? – I mean Mrs. Jeter… she makes me call her Mom, but she’s an amazing cook to begin with. She say ‘I’m the older brother Derek never had’, so I wouldn’t feel right trying to influence them one way or the other.”
Mr. Steinbrenner says, “I understand, and respect your integrity, T. Sean. Derek Jeter is lucky to have a best friend like you. Thanks for listening and here’s a token of my appreciation. ” Mr. Steinbrenner shakes my hand and slips me Mickey Mantle’s 1953 World Series ring. He then grabs a rope ladder and starts climbing it as the helicopter whisk him off to his compound.
Lorne walks over. “I think what George is asking, whatever you can do to help the Yankees, it wouldn’t go unnoticed. In fact, I have some old Jack Handey and Tom Davis sketches that got cut at dress you might want to see. Plus for the season finale I took your suggestion… Jerry Orbach with musical guest Willie Nelson.”
“Lorne, you have my word, I’ll do everything in my power to make Derek Jeter a Yankee.”
“Thanks. Okay, I have a submarine waiting for me. I have to get out of here before Billy Crystal corners me..”
“Can I get a ride back with you?”
“No”. Lorne ties a rope to a railing and repels over the side.
Once I get home I call Derek and tell him the whole story.
He starts laughing. “If they give you quarter of a million, how much do you think they’ll give me?”
“What have you heard from the Astros?”
“They’re low balling me. They want me to give them a home town discount.”
“I’m an Astros fan, but screw them. They’re chiselers. They did the same thing to Nolan Ryan back in 1988. Since I live New York, I would dig you playing for the Yankees, but I would never tell you were to go.”
“I know that.”
“That said, I will tell you where you can’t go. St. Louis or Atlanta. I hate both those teams.”
Derek laughs, “I know, both of those guys always seem to be good.”
“And don’t worry, I won’t take any more payola from Steinbrenner.”
“Get everything you can out of him, it’s not going to effect my decision one way or the other.”
Derek ends up signing with the Yankees for 5 years and I recieve lifetime season tickets behind home plate, 24 hr car service and I get to play for the Yankees in a Spring Training game.
The Astros fans weren’t happy and boycotted our restaurant. I discuss the situation with Mr. Steinbrenner and he said he’d take care of it. Three days later the place burned down. The restaurant is heavily insured and both Derek and I end up pocketing 8 million a piece. We each give 3 mill to a kid’s baseball league “anonymously” but make sure it gets leaked to the press, and the attitude softens against us in Houston.
The Yankees have a hot start. In a pre-season game against the Montreal Expos, I play 3rd base and go two for two off Dustin Hermanson before I get pulled in the fifth inning for a throwing error. I still think Tito Martinez should have pulled that one out of the dirt. Sadly, it’s my last game as a pro ball player, but I leave the majors batting a thousand, which is hard to do.
Derek Jeter’s move to New York is a success and the Yankees win the World Series and Derek’s the series MVP. I continue to excel at SNL and average 2 sketches per show. Mr. Steinbrenner helps Kitty open a new restaurant and it gets 3 Michelin stars. Which is like some super big deal, I don’t know that much about it.
Derek Jeter and the Yankees have another great year. I don’t have a bad year myself. I tie for first with most sketches on the air and earn my third degree black belt
Derek calls me before the World Series and I mention in passing how I’ve noticed Luis Gonzalez hits a lot of bloops, straight up the middle, and maybe he should cheat more towards second base. Derek does and it comes in handy in Game 7 when Gonzo punches a soft liner up the middle and Jeter is there and sends the game into extra innings. In the top of the 11th, Jeter hits a grand slam to put the Yankees ahead for good. He’s the World Series MVP for the second year in a row.
As a thank you gift, Derek buys Kitty and I a first class vacation to Hawaii. Derek’s one of the only friends that my wife likes. He’s just a thoughtful person.
In only his third year with the Yankees, Derek gets voted captain. It happens on the same day I get promoted to writing supervisor at the SNL. So we both start the year off right. With the added responsibility I step up to the challenge and average 2 sketches per show. I also win an Emmy for Best Writing for a Variety Series.
Derek doesn’t do too bad either, he leads the Yankees to their third straight title and wins the American League MVP. Frank Robinson is the only other guy to win an MVP in both leagues.
They Yankees start hot and stay hot the entire season, exactly like me at SNL. I average 2.6 sketches a show.
The Yankees sweep through the first 2 rounds of the playoffs and then hit a brick wall in the World Series and lose to the Florida Marlins. You have to give it to Josh Beckett, he was nightmare for hitters.
Derek calls me laughing when the Yankees sign Gary Sheffield. “You have to come down to Spring Training to settle this. I don’t need any distractions during the season.”
I show up to practice and Gary Sheffield immediately starts in on me.
“I hope you came to beg for forgiveness and I might let you live.”
Derek’s laughing and goes “you better watch out Shef- My boy knows Krav Maga.”
Gary Sheffield gets right in my face. He’s much taller than that woman in my Krav Maga class. That doesn’t matter. I have been training for this moment for six years. He doesn’t want it as much as I do. I give him one last chance.
“Let’s just drop this before someone gets hurt. And that someone is you.” I poke my finger in his chest to make my point.
I wake up in the trainer’s room. He punched me straight in my chest. Once they realize I’m okay, Derek and Don Zimmer start laughing.
Jeter grabs my shoulders… “You know I love you bro, but when Sheffield hit you- BAM – You went flying like you’d been hit with a cannon ball.” Derek acts it out in slow motion as tears stream down Don Zimmer beet-red face.
“Tell him how funny it was, Zim.”
“It was pretty damn funny, kid.”
“I’m not sure I’m the best audience for this joke.”
“You’re right. I’m sorry.” It takes them five minutes to compose themselves. Then, Sheffield walks by and goes “Krav Maga my ass…”
Zimmer and Derek explode.
“Laugh it up, you two. You’re like Heckle and Jeckle. A couple of magpies.”
Things at SNL are going great. I make short films called Bear City and they’re a hit. It’s got a catchy theme song that Derek help write. He’s the one that came up with the lyrics, “Bear City, Bear-Bear City.” Derek really can do anything, like help the Yankees win their 5th straight division title.
That year in the Championship series, the Yankees are up 3 games to none over the Boston Red Sox. It’s the night before Game 4 and I’m in a hotel bar and I see a bunch of Boston’s players. I hear one of them say, “We have to Cowboy Up.”
And I say “more like, get in the Cowgirl position.”
Kevin Millar tries to come after me but a couple other players hold him back. I try to let it go, but I’m just pounding back drinks and fuming.
Half-hour later I see him go to the bathroom and I decide to take care of business. I haven’t been that confident in Krav Maga since Gary Sheffield cannon-balled me, so I grab a fire extinguisher off the wall. When the bathroom door opens I swing it and hit Johnny Damon in the face and his big caveman head flies back and knocks out most of Kevin Millar’s teeth. As I run out the bar I trample Dave Roberts and break his leg.
The next day it’s reported the players were attacked by a drunk Yankee fan. and the Red Sox lose Game 4 and the Curse continues.
For the record… I like the Yankees because my buddy plays for them, I played for them, plus I have free lifetime season tickets behind home plate, but make no mistake – I’m an Astros fan, through and through.
Yankees sweep the Cardinals in the World Series.
2004 OFF SEASON
Derek becomes a free agent and I tell him “I have a couple teams I need to add to the Can’t Play For list.” Derek laughs.
“Don’t try to laugh it off, I got 2 new teams. I’m serious.”
“I know you’re serious.” That’s when he drops the bombshell. “The Astros offered me a ton of money.”
“Why would they do that? They have Adam Everett.”
Jeter’s knees buckle with laughter.
“That’s cold, Teesh. C’mon man, he’s got a good glove.”
“That’s like saying a comedian is a good guy. That means he’s not funny. And last I checked, shortstops still have to bat in the National League, right?”
Two weeks later, Derek re-signs with the Astros.
The day after Derek signs with Houston, SNL informs me they won’t be ordering new episodes of Bear City. Bummer. I wrote a feature for Bear City but Lorne is no longer interested. Okay, he was never interested in it, but now he’s really not interested.
Jeter rejoining the Astros encourages Carlos Beltran to stick around after an epic post season. They also sign Adrian Beltre to play 3rd. Then the Astros send Sean Berry, Adam Evert, Jason lane and Brad Ausmus to the Boston Red Sox for catcher Justin Varitek and an unknown minor leaguer named Dustin Pedroia.
I have a kick ass year at SNL and dominate the season easily getting the most sketches on the show and with the short porch in left field at Minute Maid park, Jeter hits a career high 36 home runs and wins another MVP award. First guy ever to win the MVP in one league, go win it in another league, then go back to the first league and win it again.
Kitty reopens The 713 in a bigger space and it’s more popular than the first time. The overlords of restaurants only gave The 713 two Michelin star. That’s still supposed to be amazing, but Kitty’s restaurant in New York got 3 stars. I think they were being greedy with the stars.
2006 - 07
More of the same, the Astros and T. Sean continue to kick ass. Derek and the Astros win the World Series, T. Sean gets the most sketches on SNL.
I leave SNL to direct a movie I co-wrote called Harold.
Jeter and the Astros are still the team to beat. My movie Harold, does good, but doesn’t get a wide release. Jeter can tell I’m feeling down.
“You’re always talking about your Bear City movie, you should make that.”
“I don’t know, Derek. People think a movie with a bunch of people in bear suits is a crazy idea.”
“I think it’s a good idea and this is something you have to do. Your Ishmael and Bear City is your white whale. I’ll put up half the money and you put up the other half.”
The next day I start pre-production, and seven months later I finish T. SEAN’S BEAR CITY.
In the World Series, the Astros drop the first 3 games to the Red Sox. No team has ever come back from 3 games until the Astros defeats Boston in game 7 scoring 11 runs in the bottom of the ninth. Dustin Pedroia is the Series MVP. The Curse Continues.
The Astros beat the Yankees in six games for their 4th consecutive title.
As for T. Sean’s Bear City, it wins a bunch of awards at Sundance, gets translated into 14 different languages and has box office revenue worldwide of 1.6 billion dollars. It makes 482 million in America alone.
Derek’s share for investing in the movie comes out to about 200 million. My share of the profits, including merchandizing, comes to right around 800 million and when I hear the Astros are up for sale, I decide to buy them.
OFF SEASON - (2009)
I’m all lined up to buy the team and we’re at the contract signing when Drayton McClain and Commissioner Bud Selig try to pull the old bait and switch.
Bud puts a hand on my shoulder. “There’s one last thing I forgot to mention earlier, T. J.”
“It’s T. Sean.”
“I’m sorry, T. Sean. So one last thing, in 2013, the Astros are going to have to move to the American League.”
“No way, Jose. The American League blows.”
“It most certainly doesn’t.”
“Then you move Milwaukee back to the American League.”
Drayton steps in, “T. Sean, calm down.”
“No, you guys are trying to change our deal.”
“Just hear me out.” Bud says with a crooked smile. “Houston moving makes the most sense travel wise.”
“No, it doesn’t. And you got this stupid idea from Bob Costas book. When I catch that little dude, I'm going to put him under a laundry basket and sit on it.”
“We’ll knock 100 million off the price if you agree to the move.”
“No, I’m good. I’ll pay full price. Move your crappy Brewers back to the AL.”
“No, I’m not going to do that.” Bud then crosses his arms like a little kid. “Then I won’t let you buy the team. What do you think of that?”
“I think you’re both weasels.”
I’ve hated guys like them since I was in grade school. I fake a quick step towards them and they both flinch. They always do.
I leave the meeting and call Jeter and he tells me I should go to the press.
“I can’t because if a reporter writes something negative about him, Selig will single them out and make their life hell.”
“If enough guys rally against it, he won’t be able to punish them all. I’ve always gotten along with the press. Let me see what I can do.”
Derek spends the afternoon on the phone and that evening articles start popping up everywhere from reporters, current and former players, all of them denouncing the idea of the Astros being strong-armed into the American League. Derek even gets that little worm, Bob Costas to backtrack and say he no longer believes the Astros should be moved.
It takes about a month, but Bud Selig finally caves and agrees to let the Astros stay in the National League. Selig forces Colorado to move the AL. Yeah, Bud’s a classy guy to the bitter end. I buy the team and immediately hire my brother, Pat, as General Manager and he signs C.C. Sabathia, who’s our opening day starter.
The Astros are slow out of the gate with a 4-23 record and I fire the General Manager. That turns out to be the spark the team needed because we end up winning the division by 13 games. In my first year as an owner, I get a World Series Ring.
I write another movie, T. Sean’s Escape from Bear City. Derek has some great notes and helps me tighten up Act II.
The Astros continue to dominate the National League and win 3 more rings, C.C. Sabathia has been dominating so I rehire my brother as G.M. and as for Derek Jeter… in his last major league at bat, Derek hits a walk off single in Game 7 for the Astros to beat the Red Sox. The Curse continues.
My movie T. Sean’s Escape from Bear City exceeds initial expectations and grosses more than 4 billion dollars.
BACK TO REALITY
Look how different things could have been. Derek Jeter would have 17 World Series Rings and the Astros would have stayed in the National League with 13 World Series Titles, and I’d own a baseball team and made 2 Bear movies.
But no, the Astros drafted Phil Nevin.