Characters In Your Fantasy League

July 13, 2024

Back in 2003 when I first launched one of the staff’s early writers, Tom Pellegrino, came up with the concept of this feature article. Every fantasy football league in America has a least a few of these characters or some resemblance of them in their leagues.

These people all exist in the same social experiment that is fantasy football. This is the fun part of the league. If you just drafted and played the games, that’s not fun. Leagues fail because of that. You need villains, heroes, and all of the characters in between. You need to make it personal among your friends, family, and co-workers, that’s what make fantasy football so great: the ability to take this great game to another level through these relationships.

Over the last two decades I have revisited Pellegrino’s list on several of my radio shows and added and modified his list as new ideas came. Here’s an updated list of characters you are sure to find in your fantasy league:


They’re the villains of the league. They’ve won the championship before and often more than once. They’re shrewd, good, tough, and they know it. And everyone in the league hates them, and they know that too. They cause you to not really work together, but to work against them. In order to have a good league, your league needs to have at least one Darth Vader. And if you are the league’s Darth Vader, feel good about it. It’s a great thing that you are part of the reason that the league is fun.


They’re the owner that seems to always have a team where four of their first six picks get hurt within the first weeks of the season… EVERY YEAR! They are worse than the SI cover jinx, and the Madden curse combined. You want this person to draft people that are not on any other fantasy teams that you own; and it’s a bonus for them to draft people on teams that you hate. They’re the same owner that scavenges the waiver wire early and often to piece together a random team every week. Be fearful of this person though, because just as you are thinking, “Yeah, but who has Boston Scott on their team for his 3-TD game?” The answer: The Black Cat, the week that they played you.


If their team were the same five years ago, you could etch their name on the trophy now. But instead of the 2018 versions, they have the 2023 versions of Matthew Stafford, Ezekiel Elliott, Michael Thomas, Adam Thielen, and Zach Ertz. But since they’ve been frozen for five years, they have not noticed that these guys are far from their prime form. They will defend their picks by saying, “If they are anything close to the way they were a few years ago… LOOK OUT!”


Have you seen the Best Buy commercial where the guy celebrates his team’s fantasy player scoring a touchdown against the NFL team he roots for? Well, that’s our Benedict Arnold. They cannot discern which is better, the “W” for their fantasy team, or the “W” for their favorite NFL team. And if you have to think about it, seek help. This is the fantasy player you don’t want to sit next to when watching your favorite NFL team.


This is the opposite of Benedict Arnold. They are the Bengals’ fan with Tee Higgins, Joe Burrow, Joe Mixon, Tee Higgins, Isaac Curtis, James Brooks, Rudi Johnson, Ickey Woods, Jim Breech, Boomer Esiason, and Chad Johnson all on their team. And while it helps their rooting interest, it does not translate into a solid fantasy football strategy. They also might not necessarily show up to the draft prepared. “Well prepared” for them means borrowing a pen and a piece of paper.


This is the person that hopes that you didn’t notice that the guys they’re trying to trade you are broken or suck. They try to get you to trade Tyreek Hill for Evan Engram, Justin Tucker, and the Bills’ defense. And then do not get why you do not want to make the deal. So then they “sweeten” the deal by throwing in Daniel Jones, but they’ll want you to add in Jared Goff. When they get no takers, after offering the same deal to the rest of the league, they’ll end up dropping Tucker during his bye week. That’s when you attack. No, that does not mean pick the person up, rather to the guy who dropped him say, “How did you drop the greatest kicker in NFL history?”


They are the opposite of Crappy Trade Person. In a way, they’re even worse. They have a glaring need, they also have someone you could really use, and you have someone they need.

You make the offer. Nothing.

You even sweeten the deal. Nothing.

You make your absolute best possible offer. Nothing.

You bribe them. Nothing.

You buy them season tickets. Nothing.

You use calculus to prove that the deal will work for both sides. Nothing.

You bring in Matthew Berry, Mike Clay, Greg Cossell, Cris Collinsworth, and Tony Romo to break the deal down. Nothing.

You try the Jedi mind trick. Nothing.

You threaten to hit them with a boat oar. Nothing.

You actually hit them with a boat oar. Nothing.

They think that you must be trading him crap and what they have must be very good. They are so afraid to pull the trigger that they refuse to use the waiver wire to drop a player that sucks to get another player. Y’know? Just in case.


They are the owner that needs constant clarifications on the rules. And they act like this is all news to them. “So let me get this straight.”, they’ll say, “You can keep two players between one year and the next, right? What if I kept Justin Herbert, Justin Jefferson, two guys that aren’t even on my roster, Derrick Henry, DeVonta Smith, and Kyle Pitts? Would that work? Why not?” They also is the person that tries to start five running backs, instead of using any wide receivers. They are perpetually looking for an angle that just isn’t there.


They like football. They seem relatively intelligent. And they just want to try out this crazy fantasy football thing that the young people seem to be talking about these days. So they draft. And their team has every player on it that seems good (because they have TV ads, are talked about on TV or radio, and have lots of sound bites.) So their roster has players that are NFL good, but not really fantasy good. However, this owner winds up going 4-9 in their first year, and hosting the league for the Super Bowl party. In every league, The Rookie always takes a beating, and then they get smart, and mix in well. But that first year…can be rough.

THAT #@$&!%* GUY

I hate That #@$&!%* Guy. That #@$&!%* Guy is guy that is involved in every major controversy in the league. He’s the guy that thinks he got hosed on the draft order. He’s the guy that realizes he made a dumb trade, and wants it reversed; TWO WEEKS LATER. He’s the guy that thinks that league is specifically designed to destroy his team and rob him of his money. He thinks that every trade is an assault against his fantasy football empire. He thinks that the waiver system is football aristocracy and pure fascism. He’s the guy that calls you at 1:15pm on a Sunday while you are at a football game, out-of-town, or a family reunion out in the middle of nowhere and nowhere near a computer to inform you that the changes he wanted to make were not allowed because the games just started, but he SWEARS that he hasn’t watched a second of football (yet, they person he wants to start the game just caught a 90-yard bomb for a touchdown, but that’s just a huge co-inky-dink) AND DEMANDS THAT YOU DO SOMETHING ABOUT IT RIGHT NOW! He threatens to quit the league mid-season thus giving you the dreaded odd number of teams. You cringe when your caller ID says it’s him. He’s just That #@$&!%* Guy!!!!


With changing diapers, lack of sleep, and everything else that comes with having a new child, this league member is thoroughly enjoying the fact that they were able to get out of the house. However, they are simply going to replay what they last remembered working. They’ll forget who moved to what team, and most of his pics will come out like a question: “Mike Evans?” They are also the owner that will take someone who retired last year, like Tom Brady.


Believe it or not, doubles as “The Whipped Owner”. They are the person that keeps hitting refresh on his computer screen to see if that 4-yard run from Aaron Jones got them anything. Mainly because they’re either A) beyond obsessed with fantasy football; or B) their significant other is thinking about other ways they could have spent $20-500 rather than on your stupid stat game. This owner is like a stock market day trader, constantly seeing what a tiny occurrence did to their score instead of waiting for SportsCenter or looking around online at nine at night like the rest of us. They do this because if they had to report that they lost a fantasy football game, it would start another fight about money.


Routinely last in the waiver wire priority order, The Flipper has two or three moves to make every week. Their roster in the first week of the season looks vastly different from their roster at the end of the season. Usually they have about six of the same people.


They are the person that takes the phone calls. They set up the rules, interpret the rules, and run the league. And they deals with Flipper, Day Trader, The Rookie, The Lawyer, That #@$&!%* Guy, Crappy Trade Person, and Darth Vader all at the same time. And they’re the one drinking Pepto Bismol like they’re cold ones by Week Twelve.


Every league has a Speed Bump on draft day. In leagues that draft at bars you may have multiple speed bumps. The Speed Bump is the person whose turn to draft you can’t wait to come up for because you’ve got to pee. They are the reason the commissioner has to add a draft time rule and start displaying a clock on draft day. In auctions they’re the owner that always offers up a bid at the very last second after “going once, going twice”. Even in online drafts the Speed Bump waits to their 89th second on the 90-second clock to make a pick. The worst speed bumps are in slow drafts where you better believe they’re going to take at least eight hours to make every single pick.


She is the owner that everyone laughed at the commish when he asked if she could get in the league, but soon nobody wants to lose to. Losing your fantasy game is bad enough, but losing to her is the worst…and she lets you know it. She is the league’s biggest smack talker and most shrewd manipulator. Her trading skills don’t follow the norm so she is hard to read. The worst part is that even if she does struggle you can’t talk smack back because you’ll only look like a jerk.


This owner just retired and has a little too much time to spend on fantasy sports. Not only do they play seven teams seasonally, but they set like 25 daily lineups a week. They are not playing for an income nor do they make a ton of money doing it. They simply have too much time on their hands. This owner gets pissed when you don’t reply back to a trade offer within minutes and soon will be trying to call you to ask you why you haven’t responded. They are the league’s most stubborn player and the one most resistant to change. They’re still arguing to keep things as a TD-only league just like we did in 1993. They are the one that needs help with the league website every year and has to have everything repeated back due to bad hearing. None of it matters though because he’s just happy to be back for another fantasy season.

Here are some recent additions from my radio listeners…

The “Yes Dear” guy brings a spouse as the only female who helps (tries) draft the team.

The “Pimp” brings a hot girlfriend to run the draft board as a distraction for other teams.

The “Awful Pick” person. Not because their picks are necessarily awful, but rather because they berate everyone else’s picks with a line like: “awful pick”. What makes it most amusing is that this person always finishes in the bottom half of the league.

The “Biff Tannen” owner. (From Back to the Future) They are horrible at trash talking, not clever, and often they also have a horrible team, but they are the most obnoxious person in the league.

The “Bluffer” always throws out different names on who they are taking prior to draft day, because they pick before you.

The “Favre” always calls it quits mid season & then by next season he’s back to being all in.

The “Telecommuter” always has scheduling conflicts between the same 2 leagues that have forced me to be that guy that everyone is waiting to hear from once I go on the clock. They feel like a jerk, but under no conditions will auto draft.

The “Doomsday Owner” is the one that predicts doom for other owner’s picks on draft day. Throws out quips like “isn’t he injury prone”, “this is the year he falls off the cliff”, etc.

The “Cultivator” is the person when anyone has success in the league he chimes in with, “I could’ve had him in the third round, but I passed on him”. Or “I had him on my team but I had to dump him back into the waiver wire”. They basically take credit for your success. The Cultivator!

The “Taco/Andre”. They are the most clueless owner, but lucks into wins and makes a deep run in the playoffs.

The “Fantasy Philanthropist” constantly is donating of hundreds of dollars to fantasy leagues everywhere and never gets any money back in return.

The “Accidental Drunk” is the person who doesn’t mean to get buzzed on draft day and by Round 12 blacks out. The listener that submitted this said in their league there is a “take-a-shot” of Fireball penalty for any draft day error (i.e. drafting a player already drafted, having clock expire, etc).

The “Flip Flopper“. Expanding on the Flipper, we have a Flip Flopper. They drop a player, then add them back to the roster, then drop them again. Happens multiple times a year and is pretty funny to see on Tuesday morning. Just make up your mind.

The “Repicker” is they guy that drafts a guy already drafted.

The “Rule Waster” is the guy that brings up the same rule change every year before the draft that gets voted down 1-11 every time.

*Follow Dan Clasgens on Twitter at @DanClasgens and join the conversation.

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2 comments on “Characters In Your Fantasy League

  1. Brad Campbell Jul 29, 2017

    We had the “Inconvenienced Guy”. If the draft time didn’t fit HIS SCHEDULE he’d threaten to quit, and then constantly complain the draft is taking too long because HE has other things to do.