We all want to win some coin when we play fantasy sports. What if you want to crank things up to the next level, though, and instead of playing for money to take your significant other out to dinner you’re interested in joining a league where you can take her to dinner in Paris? This article shares some tips to keep in mind if you’re going to enter a high-stakes fantasy baseball league.

FIND A SOURCE YOU CAN TRUST

There are some leagues out there that play for money.

Not all of them payout the winners.

Do your homework.

Make sure you chose a company that is reputable and will be able to meet its financial commitments.

KNOW YOUR COST/RISK TOLERANCE

Be responsible.

Know how much disposable income you have to throw around. Don’t be one of those parents who can’t take his/her family to dinner because you’re spending all your money trying to hit a home run in fantasy sports. Be objective, rational and safe.

Note the term disposable income. Spend that. Don’t take chances with the money you need to live on.

LIMIT YOUR LEAGUES SO YOU CAN FOCUS

The first couple of points seem obvious. This one, maybe not as much.

We’ve all been there, and by that I mean we’ve all signed up for five leagues and feel good about it. Then our co-worker asks us to join another league. The next week your girlfriend challenges your manhood so you add another league to whip her ass. Then you run into your old high school homie at a bar Thursday night (yes it’s ok to drink Thursday night) and six Jack & Cokes later... yep, another league. In the end your five leagues swell to nine and you’re all kinds of committed and busy.

Yes, we’ve all been in this scenario before.

When you do more than a handful of leagues, your hobby can quickly become a job. You have to make sure you keep setting your rosters properly and free agency is a time crunch akin to watching an entire baseball game every Sunday. Life doesn’t stop, of course, so what happens? You run out of time for everything. That team in sixth place come mid-May? Maybe you spend four minutes on that one but that team in third, you spend like 20 minutes looking at it. Wait, what are the rules of that league? Was that the points league that counts innings or the one that doesn’t? Do we have DL spots in this league?

If you’re spread super-thin, things fall through the cracks. You probably don’t care too much if your old high school teammate beats you in fantasy, but what about that league with your girlfriend? You can’t have her beat you. Worse yet, what about that league with your co-worker in which you paid money to enter? You gotta pay attention to that one, right? Still, if it’s one of nine leagues maybe you just don’t have enough time...

Be honest with your time. How much can you afford to put into a league? When you’re talking a high-stakes league, understand that those folks are very serious. Someone is working harder than you, perhaps even multiple people in a money league, so don’t do the entire league a favor and only sort of pay attention.

Make sure you have the time needed to pay attention to every aspect of the league. If you aren’t willing to commit to that level, you’re simply donating your entry fee.

ARE YOU TRYING TO WIN YOUR LEAGUE OR THE OVERALL POOL?

You have to decide off the top how you want to play your league. Are you going to be happy taking down your league mates and doing something likely tripling your money? Will that be enough for you? Or, are you in the game to win the life-changing money you would rake in if you won the whole tournament? You have to decide.

Think investments.

If you're trying to win just your league, and not the overall title, think along the same lines as investing in a mutual fund. Invest safely, with little risk, and chose those assets expected to deliver solid returns without being overly risky. Steady and stable wins the day here.

If you’re trying to win the whole thing, well, then we invest all our money in that new tech company and hope they don’t go the way of the Samsung Galaxy Note 7 Phone. If you’re going for the overall win you take more chances. There are players about whom we all say, “if he could only stay healthy,” and these are the type of players you target if, this year, the goal is to win a gazillion dollars. You roster the risk that comes with Giancarlo Stanton, Rich Hill and Stephen Strasburg. The upside is immense. Of course, each man could spend more time on the disabled list than on the field, so the downside is similarly massive.

Decide before hand how you want to play it.

 

PLAY IT STRAIGHT

You will see folks trying exotic strategies.

Folks will punt saves and try to win the other categories.

Some will punt steals and try to power up in the offense categories.

Some will target a team of injury-prone players and hope they will all stay healthy.

Others will draft only players who are 26 years of age or younger.

Etc., etc., etc.

If you want to put your team together in this way, you’re better off playing in a league for less cashola. Try those exotic things with your friends. When you’re playing for real money, don’t try to outsmart the game – just play it straight.

BE PROACTIVE, NOT REACTIVE

In a league like this you have to be forward-thinking.

On draft day, you have to be willing to assume some risk, even if you’re “playing it straight.” In high-stakes leagues people always have their eye on the prize which means they are willing to be aggressive with rostering players. Ben Zobrist and Gio Gonzalez will likely be drafted well after their ADP suggests, but guys like Alex Bregman and Alex Reyes... those type of youngsters will often find themselves flying off the board ahead of ADP. The reason being that people are projecting what these players could be and are drafting them accordingly, as many think that they cannot win the league unless they take a risk. Therefore, people prioritize youngsters as a risk worth taking on draft day.

During the year, being proactive means attacking the waiver-wire with uncommon vigor. You won’t be finding that closer on waivers four days after he was named the closer by his manager. Someone in your league noticed that the previous “closer” was struggling so two weeks ago they added that middle reliever-turned-closer you were interested in adding. That rookie who was just called up? Nope, he ain’t there either. A league-mate of yours picked him up 10 days prior when they noticed he was batting .385 with six homers over the last three weeks while that 34-year old veteran at the big league level was merely taking up space hitting just .211 against right-handed pitching.

Another tip. When working the waiver-wire don’t just filter players by performance the past 10, 14, 21 days or whatever you normally do. Make sure to think your way through the process as well. Someone else is, so if you aren’t, you’re losing.

UNDERSTAND YOU WON’T BE ABLE TO TRADE

If trading is your jam, then high stakes leagues aren’t for you. To avoid any concern over collusion or any type of funny business at all, high stakes league do not allow trades. If you lose, it will because your guys stink, not because some moron in your league deals a .229 hitting Joey Votto for a .314 hitting Travis Shaw on May 1st (those were the batting average of both men on May 1st, 2016. In fact, Shaw had an .885 OPS at the time while Votto was at .640. We know how this one ended with Shaw posting an OPS of .726 versus the .985 mark of Votto). You will win/lose your high stakes leagues based on your draft and the way you utilize the waiver-wire. That’s it.