Fantasy Life: The Outrageous, Uplifting, and Heartbreaking World of Fantasy Sports from the Guy Who's Lived It

by Matthew Berry

  Luckily, turnabout is fair play, and the woman gets the last laugh in the next story, where Jameson Singer talks about the Fantasy Game of Thrones League, where his buddy Alex owned a team. As did Alex’s girlfriend, Carly. Who wasn’t happy when she found out Alex had cheated on her. I’ve heard of women getting revenge by dating another friend or dishing secrets, but Carly hit Alex where it really hurts: she traded Arian Foster to a guy in her ex’s division for a backup. The happy recipient of Foster (the number one running back in fantasy at that point) ended up winning the division, the girl quit the league, and everyone learned a valuable lesson: hell hath no fury like a woman who owns Arian Foster scorned.

  It’s not just romance or avarice that fuels some trades. Sometimes it’s a bet or just sheer boredom. In Will “Wild Bill” Finnegan’s Steve T DFL Fantasy League, need met bizarre opportunity. An expansion team was desperate for players, and his roommate’s fish had died. The league bet him if he ate the dead fish, he’d get Jacoby Jones and Jacob Hester.

  So basically, he got screwed twice.

  But apparently that was business as usual for Will’s league. They are a goofy, trading bunch of fools.

  One time they took all their kickers, wrote their names down on separate pieces of paper, and put them in the blender. “We put the blender on without the lid, and whoever popped out when it was your turn, that was your kicker.” They also did something similar with their worst wideouts and a microwave. Kickers in a blender, wideouts in a microwave? Get out of the kitchen, guys. Go watch some football.

  Speaking of the kitchen, that’s exactly where Myles Pappadato’s Papalino’s Alumni League started eight years ago. A 10-team baseball keeper league comprising guys who used to work at a pizza place, they were all at a poker game in April of 2012. Myles remembers that, “after some adult beverages,” they got the idea that the poker winner could trade for anyone he wanted who was selected after the fifth round from one of the losing teams.

  Team Bandits prevailed and selected Tigers pitcher Doug Fister from Team Bad News Bears. But how many times do we have to warn of messing with the fantasy gods? The next morning, “Team Bandits posted a victory rant on our league message board and demanded the trading of Fister to his roster.” When reminded he had to send someone back for Fister, “the Bandits quickly replied that they knew exactly who to send back to the losing team, ‘that scrub from the Mets, R. A. Dickey.’”

  Final stats for Doug Fister in 2012: 10 wins, 137 strikeouts, 3.45 ERA, 1.19 WHIP, 162.2 innings.

  And for that “scrub” R. A. Dickey? 20 wins, 230 strikeouts, 2.73 ERA, 1.05 WHIP, 233.2 innings. He won the Cy Young Award that year.

  Chalk up another “w” for fantasy karma, as that was obviously not what Team Bandits had in mind. A feeling I could relate to as I tried to launch RotoPass.com. What was supposed to be a quick way to make a little money proved to be much more challenging. (Always the case, right?) Since fantasy sports is seasonal and many of the premier websites in the industry have very different price points, it took a while to figure out the exact business model: Do we charge by sport or by month? How much do we charge? One site costs $100 and another costs $20—how do we provide access to both sites so each website owner feels like he’s getting proper value with his cut of the total price? What do we do with existing customers of the sites if they upgrade to a RotoPass? And then how do we track them? The whole thing was a nightmare to figure out, especially since I was still doing my day job of writing movie scripts.

  Once I had a workable business plan, it took even longer to convince all the established websites to go along with an unproven idea run by an unproven guy. I went through many, many proposals, phone calls, and meetings with designers, lawyers, tech guys, and, of course, the other fantasy sports website owners.

  Took me over a year, but eventually it all got done, and it launched in June of 2004 while I was still writing for Rotoworld.com.

  Well, until I was fired.

  TIME-OUT:

  Trade Advice from My Late, Great Uncle Lester

  “Maaaaaaaaaaaatthewwwwwwwww.”

  Even though my name is only two syllables, he always stretched it out so that it sounded like four, in that unmistakable drawl.

  “Maaaaaaaaaaaatthewwwwwwwww,” he would say as he chomped on his cigar and adjusted his trademark 10-gallon hat. “Come philosophize with your old uncle.” And with a huge smile on my face, I would bound into his office and do just that.

  My great-uncle Lester Gold was 88 years old when he passed away February 28, 2011, and many of you reading this didn’t realize it at the time, but the world became a much lesser place that day. It’s rare, of course, that you have a close relationship with your great-uncle, but Lester was a rare man. It was impossible not to have a close relationship with him.

  My father, no slouch in his own right, gives Lester much of the credit for his focus, ambition, and success. Much of my drive, ambition, and focus comes from my father and my Uncle Lester, so, really, it all comes from him when you get down to it.

  I don’t know that there is any definitive way to judge whether a man had a successful life, but whatever metric you wanna use, Uncle Lester blew it out of the water. A self-made and self-taught man, Lester grew up the son of poor immigrants. When he was 13, his mother passed away, so he had to start working to help support the family. “I’m a peddler,” he would always say. “Just a peddler.” But Lester wasn’t “just” anything. He started with junk, biking back and forth between junkyards in Denver. Soon he had scraped together enough to buy his first car for $5. And then he promptly sold it for $10.

  He took that $10 and bought another car and sold that one and kept buying and selling cars and eventually was able to open his first used-car dealership. He was 18 years old.

  That year was a good one for my uncle. Because that was also the year he got together with my Aunt Cookie. They’ve been together for 70 years now, and nothing as simple as death is going to keep them apart. Their souls are together for eternity.

  My Uncle Lester was fantastically successful in business, opening up a chain of car dealerships and then getting into oil for a long time and then land development. I couldn’t possibly tell you how many millions of dollars the man was worth because he never flaunted his wealth. The only time it ever came up was to either donate it (he was very generous) or spend it on family.

  So many memories. Once, when I was 14 or so, I was having lunch with Lester and Cookie, and I asked him naively, “Uncle, you’re so successful. How do you do it? What’s the secret?”

  “Maaaaaaaaaaaatthewwwwwwwww,” he said, “it’s very simple. I figured out a long time ago it was just easier to make more money than it was to stop your Aunt Cookie from spending it.”

  My aunt cackled in that great laugh of hers and nodded. “He’s right. I grew up on a farm. And we had work horses and show horses. I told your uncle on our first date . . . I’m a show horse.” And they both laughed together. They did that a lot.

  As you might imagine from a man who started working at 13, served our country overseas in World War II, and was a self-made millionaire with the same girlfriend—as he always referred to Cookie—for seven decades, my uncle had a lot of strong opinions backed up by a wealth of life experience.

  He not only had a specific point of view on everything, he had a colorful phrase to describe it. We called them “Lesterisms,” and when I would go to Denver and “philosophize with my old uncle,” he would share them with me.

  I have found that Lesterisms are helpful in life and in fantasy sports. And before you flip to the next chapter because you think you know everything you need to about winning at fantasy—or life—consider my uncle, who always felt that we should never stop learning.

  As a man dedicated to the Jewish faith, he started a weekly Talmud study group with a local rabbi. When he was 64. And studied it for the 24 years up until his death. If Le
ster was still learning at 88, you can take a few moments to let my uncle help you the next time you are doing a fantasy trade. Here are some of my favorite Lesterisms.

  “Don’t make a decision until you have to.” Too many times I see players panic and make a deal because “this guy is coming back from injury,” or “I don’t have a quarterback for my bye week in three weeks.” Fantasy value changes all the time. Don’t make a deal or a decision on a player until you absolutely must. This is especially true in keeper leagues. I turn in my keepers at the very last possible minute. He can be a star one minute and sitting on the bench the next for a variety of reasons. Don’t make a decision until you have to.

  “Don’t risk what you cannot afford to lose.” A deal is not just about the upside but also about the downside. If this deal goes completely south, can your team still compete? People always look at the upside of the deal, but having a low downside is just as important. Understanding both potential outcomes of the deal will help you evaluate it better.

  “In the old used-car sales days, if a guy was trying to trade in one car for another and asked if the car leaked oil, that meant his car leaked oil.” It’s not just about what you are saying in the negotiation, it’s about what the other party is saying. Listening is much more important than talking when making a deal. Which is why talking in person or on the phone is much better than just emailing the guy a trade offer out of the blue. You want to get the most out of the deal? Talk. And listen.

  “If you’re in a poker game with five guys and each guy has $100 and you’ve won $400, it’s time to leave. You’ve already won most of the money.” . . . “If you can get 80 percent of what you want in a deal, take it. Most guys screw it up trying to get the last 20 percent.” . . . “It’s a good deal only if both sides are satisfied.” These three pieces of advice all tie together. The idea is to improve your team. Making it a superpower is great, but unrealistic in leagues where people know what they are doing. Don’t be greedy. Get a deal done that helps you, not a deal that kills the other guy. You’ll want to trade with him or her again, and setting fire to the earth doesn’t do that. Nor does gloating about the trade afterward to the league.

  “Don’t trade something you need for something you don’t.” Seems simple, but you’d be amazed how many people get enamored with big-name players and superstars without considering whether their team actually needs that big-name player. Always think about what your starting lineup will be once this deal is done, and whether that lineup is better than what you have. Tom Brady is great, but if you have to bench Drew Brees to play Brady, that’s not really a great trade for you since I’m sure you had to give up a stud RB or WR for Brady.

  “The best way to double your money is to fold it up and put it in your pocket.” Sometimes the best trades you make are the ones you don’t. It’s not always necessary to make a deal. Always be willing to walk away.

  “You don’t need to tell a man what he already knows.” Part of the art of negotiation. Tell him something he doesn’t know. He’s aware that his point guard can’t shoot or that his quarterback is a bum. Talk up your players. Tell him something to give him hope, not make him feel worse.

  “Do not presume an outcome before it occurs; more times than not you will be wrong.” Put yourself in a position to have the best possible chance at success, but understand it is just a chance. No deal is a slam-dunk. Nothing is guaranteed, so don’t treat any player or situation as such.

  “When a mouse is caught in a trap, he’s not thinking of the cheese, he’s thinking of how to get out. But once he’s out, he’s thinking about the cheese again.” This is about understanding that a deal is not just about what you get. It’s also about what the other guy gets. Understand the point of view of your opponent (and if you don’t know his or her point of view, listen) and realize that his point of view may very well change after the deal is done (or not). Tread carefully before, during, and after the negotiations.

  And my favorite . . .

  “Never chase a woman, a streetcar, or a deal.”

  My Uncle Lester preached being conservative in business (“Lucky is a bad business plan”) but being adventurous in life (“You never know how big of a ditch you can jump over until you fall in”).

  He had a million of them. “If you tell a lie, you better have a really good memory.” “Borrow money when you can get it, not when you need it.” And “Anyone can get along with easy people. A great executive can get along with difficult people.”

  But the one he used the most was the answer to a question. Every time I saw my uncle, I’d ask him how he was doing. He answered the same every time.

  “Still climbing that mountain, Maaaaathewwww. Still climbing that mountain.”

  He was never satisfied. He felt there was always something he could improve on and do better.

  As the Intermountain Jewish News wrote about him, “The word ‘colorful’ was invented for Lester Gold. We might call Gold, who died this week, a philanthropist, an astute businessman, a behind-the-scenes leader who made things happen. We might say all this, and even add that he was an extraordinarily devoted husband and father and grandfather. We may say all this, and be right, and still fail to capture him.”

  By his example, Lester set high expectations for anyone in his orbit. He and Aunt Cookie had three daughters. Those three daughters had seven kids. Those seven grandkids have 14 children of their own, with another on the way. They all live in Denver, very close to their Poppy and Gammy. I can still see my uncle now, sitting in his white recliner, a huge grin on his face, as any number of kids or grandkids or great-grandkids ran around with shrieks of joy.

  I know I’m not anywhere near the kind of man my uncle was, and I can’t imagine how I could ever be. But it’s a worthy goal to shoot for. So I’m still climbing that mountain.

  8.

  Not All Trades Go Smoothly

  or

  “We Created a Second Hakeem”

  They weren’t the only things in life Josh G. cherished. But they were up there.

  One was Josh’s best friend of 18 years. Another was being commissioner of their fantasy basketball league, Pimps Don’t Cry, a job he took seriously. And those two items were now conflicting.

  It was a few months into the season, and “Dan” (the friend) wanted a rule change. By having unlimited transactions in their head-to-head league, it “was punishing him for having a good draft,” Dan argued, “as he couldn’t drop his good players to fill in on off-days, the way others could.” Josh understood where he was coming from, but “I told Dan I was uncomfortable changing any rule after the season had started, especially since this was a money league.”

  Back and forth they went, with Dan pressuring Josh and Josh holding firm. And so, unable to get his way on the rule change, Dan used the fantasy trade, often a beautiful thing, for less than beautiful purposes. Dan and his brother dumped their entire teams in one-sided trades to try and destroy the league. They then both quit the league. Josh tried to make peace, asking the guys to stay and see if they could work something out. “It’s too late for that” Josh was told.

  As Josh let me know, “A few hours later, Dan texted me and told me that he had replaced me as a groomsman in his wedding.” Insane, right? Josh adds, “He was kind of known for throwing temper tantrums like an eight-year-old. While it sucks to lose a friend, I had been getting tired of his self-centeredness for years.”

  Still . . . 18 years of friendship is a long time. It’s been two years, and they haven’t spoken since. Someone who was supposed to be in his wedding. Over fantasy basketball. No one takes fantasy more seriously than I do, and even I will tell you it is not worth ruining relationships over, let alone with your best friend for almost two decades.

  Listen, you didn’t read this book for me to lecture you about the importance of relationships. Or even fairness. But the fantasy trade? That’s my wheelhouse.

 
; I hate hate HATE the veto. It’s the coward’s way out. If I were suddenly made the ruler of all things fantasy, there would never be a veto except in cases of obvious, provable collusion. And in that instance, only the commissioner or host website for the league should veto.

  They say there are only three things in this world you can truly count on: death, taxes, and that when you make a fantasy trade, someone will bitch about it. Which is a shame because people should almost never complain about a trade.

  Understand these two key things:

  First, the art of negotiating is a skill in fantasy. That’s part of being a general manager. A huge part, in fact. It’s a skill that is admired and sought after in real-life general managers. Why should it be any different in fantasy? Second, it is not your job to coach someone else’s team. If you think that tight end isn’t nearly enough for that quarterback and running back combo, it doesn’t matter. The only thing that matters is that the guy getting the tight end thinks so. Everyone should be allowed—encouraged, in fact—to coach his or her own team. Even if it’s stupidly.

  Because I got news for you. No one ever knows. I remember one of the first email flame wars I got into about a trade. In the Doug Logan League from chapter 2 (a dynasty fantasy football league), I traded a package of players for, in essence, Brett Favre, then one of the best quarterbacks in fantasy. It was a depth-for-a-superstar deal, perfectly legit. But the league went nuts because the only quarterback the guy was getting back was a recently promoted backup who got the job only because the starter had been injured in preseason. I argued that the point of the deal was to give him depth at RB and WR, which is what the guy said he wanted, and the backup was better than they realized. He was happy, I was happy, what’s the issue? On and on they bitched. Until about week three or four, when they realized the backup QB I had dealt—Kurt Warner, in his 1999 “greatest show on turf” season—was better than Favre would ever be.