Drafting these players could make or break your fantasy hoops season

Jimmy Butler's fantasy value hinges on where he lands. Troy Taormina-USA TODAY Sports

How competitive is your league?

It's a simple question. One you should consider closely before entering your fantasy draft.

The tougher your league, the more risks you'll have to take. To win? You're going to have to roll the roto dice.

Rolling the dice means confronting the prospect of drafting a single player that could, all on his very own, make or break your season.

At its core, winning in fantasy hoops is about one thing: maximizing return on your draft-day investment. You need to create differentiation between your team's numbers and your fellow pseudo general managers. To do that, you'll have to balance risk versus reward in some extreme configurations.

If you're in it to win it, you'll need to venture out of your comfort zone and take a player with at least one red flag.

Red flags come in all shapes, sizes and hues. There are a lot of "maybes" in fantasy hoops.

Maybe a player is coming off a season-ending injury and has a return date you can't trust. Maybe a player just switched teams. Maybe a player just got relegated to a sixth-man role. Maybe a player is getting up there in years. Maybe a player is still a couple of seasons away from his peak. Maybe a player has a key statistical flaw you'll have to build the rest of your team around. Maybe a player is playing for a coach he can't stand ... and the feeling is mutual.

I play in a lot of expert leagues. To win in those, I'm looking to take at least two big swings. Players that might scare other experts off, but will provide the statistical differentiation I'll need to succeed.

Let's take a look at some polarizing options that could single-handedly make or break your season.

(For the purposes of this discussion, I'm going off of our preseason points rankings.)

PICK 1: Giannis Antetokoumpo, SF/PF, Milwaukee Bucks

Do you take Antetokoumpo No. 1 overall in a points league? Will he finish the season at No. 1 on the Player Rater? There's no question the Greek Freak is a top-five asset, but is his considerable upside worth risking a No. 1 overall pick over more established uber-talents like James Harden and Anthony Davis?

If you're picking No. 1 overall and you miss -- even by a few draft slots -- the squandered value can tank your team.

If you wager on Antetokoumpo at No. 1, you're betting on the 23-year-old's considerable upside. Unlike Harden and Davis, Antetokoumpo still has room to grow. In 2017-18, he only posted a middling 76.0 FT percentage. And although his 3-point production improved as the season progressed, he still only finished with a 30.7 3PT percentage.

With Antetokoumpo, you're also betting that new coach Mike Budenholzer will be as fantasy-friendly as he was in Atlanta. And that with Brook Lopez stretching the floor at the 5, Antetokoumpo will have more space to operate.

One area where Antetokoumpo beats out Davis and Harden: durability. He's never played fewer than 75 games in a single season.

When it comes to points leagues, think of said player's offensive system. With that in mind, I think Harden's a safer investment. Playing in Houston's offense makes him my No. 1 pick.

But if you want to go for it at the top of your draft, Antetokoumpo's your man.

PICK 6: LeBron James, SF/PF, Los Angeles Lakers

Can LeBron keep up his age-defying pace of 2017-18? Should he even try? Last season -- at age 33 -- LeBron led the league in minutes played while delivering perhaps his finest fantasy campaign.

Now with a developing, but deeper, supporting cast in Los Angeles, LeBron supposedly won't be called upon to repeat last season's 27.5 PPG, 8.6 RPG, 9.1 APG, 1.8 3PG. (Let's presume there will be a drop in volume: LeBron's usage rate probably drops back beneath 30.0.)

Can he make up for it in efficiency? History and the numbers say no. His TS percentage last season was already a gaudy 61.9. His PER has been trending downward since 2012-13.

Pick No. 6 would be when LeBron would start to make sense. But going into this season -- what feels like a developmental year in El Segundo -- No. 6 feels like a reach. I'd be more comfortable taking him in the 7-10 range.

PICK 10: John Wall, PG, Washington Wizards

The knee and the 3s. Those are the two factors that will decide whether or not Wall backs up a late- first-round selection.

First, the knee. It was tough to watch Wall last season... before he finally got his balky knee cleaned up. The knee was to blame for Wall's depressed 2017-18 season averages (19.4 PPG, 9.6 APG, 3.7 RPG).

Wall was a different player after he returned for the playoffs, averaging 26.0 PPG, 11.5 APG, 5.7 RPG, and 2.3 SPG. You can't count on those gaudy numbers over the course of an entire season, but a return to 2016-17's 23.1 PPG, 10.7 APG, 4.2 RPG and 2.0 SPG feels reasonable.

Second, the 3s. Wall will show in the volume categories, but his fantasy upside is largely governed by his 3-point shooting. He's displayed a scary amount of variance in this category over the course of his career (percentages of 29.6, 07.1, 26.7, 35.1, 30.0, 35.1, 32.7, 37.1). For all of his injury troubles last season, Wall still managed a career high 37.1 3PT percentage.

If Wall can combine last season's 3-point shooting performance with his 2016-17 volume, he'll be worth the 10th pick.

PICK 11: Ben Simmons, PG/SF, Philadelphia 76ers

You know some of what you'll get: triple-double potential. A player with a positional qualification (PG/SF) that's special in fantasy. But like Antetokoumpo, a big bet on Simmons is a bet on untapped upside.

And like Antetokoumpo, the upside lies in the outside shooting. Can Simmons expand his shooting range to the point where he even considers attempting a 3-pointer?

Early reports and quotes from Simmons would answer "no."

But even if he doesn't start raining 3s, there's another area Simmons can improve: free-throw shooting. After depositing a paltry 56.0 FT percentage, he's got nowhere to go but up.

The triple-double capability sets a floor for Simmons that's still fairly high. But No. 11 is about when I'd start considering enlisting his services. His lack of commitment to expanding his shooting range is going to keep him out of fantasy's top 10.

PICK 13: Andre Drummond, C, Detroit Pistons

Can Drummond continue to improve on last season's career-high 60.5 FT percentage? If the answer is yes, then he'll be worth a second-rounder in points leagues. Last season's pseudo-competence at the stripe placed a spotlight on Drummond's many fantasy gifts: mega-elite rebounding, 3.1 steals+blocks, and a sneaky-good 3.0 assists per game.

PICK 17: Kawhi Leonard, SF, Toronto Raptors

Leonard is the 2018-19 season's weightiest risk/reward question.

Let's skip analyzing why Leonard forced his way out of San Antonio. Try not to dwell on how happy he is to be playing in Toronto. The fundamental question: Is Leonard healthy enough to return to his heady 2016-17 form? (In case you forgot, in 2016-17 Leonard averaged 25.5 points, 5.8 rebounds, 3.5 assists, 2.0 3s, 1.8 steals, and 0.7 blocks.)

If healthy and motivated, Leonard is a top-five fantasy asset. The motivation is all there: Leonard is in a contract year. And all of the initial reports on his health have been positive. Leonard's participating in drills. He's saying all the right things. He's on a team that is going to move heaven and earth to make him want to stay.

Our rankings peg Leonard as a late second-rounder. I say he's worth more than that. I think he comes close to 2016-17.

If you want to make a splash? Take Leonard as early as seven overall and repeat the mantra: contract year.

PICK 18: Joel Embiid, C, Philadelphia 76ers

If he makes it through the season in good health, Embiid could challenge Karl-Anthony Towns for best pure center in fantasy.

That's a big "if": Embiid was relatively healthy last season, and he still only played 69 games. It's going to take a couple of draft seasons for Embiid to escape the stigma of needing to have his workload managed. But that stigma is creating a gap between Embiid's perceived value and his actual value.

But if Embiid averages over 30 minutes a night, and plays in at least 70 games? He becomes a top-15 player at worst.

The key decision on Embiid: Where do you think he ranks among other centers? Where is Embiid's floor? At worst, I'd place him above Drummond in a risk/reward consideration, probably tied with Jokic for third-best center.

Center is fantasy's scarcest position this season. Finding centers that are even replacement-level competent at the free-throw line is a tough proposition, and Embiid (76.9 FT percentage) checks that box.

If you're feeling lucky, make Embiid the next center off the board after Towns.

PICK 19: Jimmy Butler, SG, Minnesota Timberwolves (as of this writing)

Preseason holdouts coupled with trade demands present a polarizing dynamic. But this feels more like a training camp holdout to me. Also in a contract year, Butler would be hard-pressed to sit out the regular season.

Minnesota doesn't have to trade him. If he stays, you know you're getting a player with top-10 upside. (Last season, Butler chipped in 22.2 points, 5.3 rebounds, 4.9 assists, 1.2 3s, and 2.0 steals.)

But if Butler forces a trade? His fantasy value shifts depending on destination. If he goes to his preferred destination -- Miami -- I see his production staying about the same. The Clippers? It stays the same.

But if he goes to the Knicks or the Nets? We enter murkier waters. While Butler would be the unquestioned number-one option for both teams, both teams offer shaky supporting casts. Either way, he'd be in for a rebuild, and rebuilds tend to cause a lot of statistical variance.

You're taking a calculated risk with Butler. But if Butler comes up aces, you'll get late-first-round value for a late-second-round pick.

PICK 31: Devin Booker, SG, Phoenix Suns

If he stays on the court, I think this is the season Booker cracks the top 20 overall. If you're still deliberating on whether to take him at No. 31, you need to start planning out your fantasy baseball team. He's a reasonable roll of the dice at the end of your second round.