Bill Simmons: With my beloved Celtics stuck in Rebuilding Mode, I find myself rooting for LeBron’s Cavaliers to give Cleveland its first championship in 50 years. How they handle a hypothetical Kevin Love–Andrew Wiggins trade is crucial for that quest. What should they do? Here at Grantland, we couldn’t resist passing along our advice. I’m writing an expanded take, and then we’re turning it over to some of our other writers for their quickie takes.

Lemme just say, it’s an honor to be hypothetically working for Dan Gilbert, one of the luckiest men in professional sports, as well as someone who did just about everything wrong for five solid years … only to be rewarded by winning the lottery three times in four years while also improbably winning back LeBron James. I really hope some of his luck rubs off on me. Here’s my Love-Wiggins plan in three parts:

First, I’d convince Gilbert that, instead of doing the wrong thing every time and improbably having it work out in our favor, we should attempt to make the right decision for once. This would be part of a bigger game plan that I’m tentatively calling “Don’t Do the Wrong Thing Every Time Anymore.”

Second, I’d convince Gilbert that the Timberwolves don’t want to trade Love yet. If they did, they would have traded him before the 2014 draft, when they could have scored the biggest package of draft picks for him AND picked at least one of those players. They’d much rather just keep leaking out that they’re continuing “talks” with Golden State about a Love–David Lee–Klay Thompson deal even if the Warriors have done everything short of putting up billboards around the Bay Area that read “WE ARE NEVER TRADING KLAY THOMPSON.”

My theory: Minnesota GM/president/coach/pooh-bah/czar/second-luckiest man in professional sports because how the F is he this powerful???/head honcho Flip Saunders has been in job-preservation mode ever since he snookered Glen Taylor into giving him that job. Let’s say you trade Love, one of the league’s 10 to 12 best players, and he comes back to haunt you on another team. Or let’s say you land a young “stud” in that trade who doesn’t turn out to be exactly what you thought he’d be, or you make a high lottery pick that isn’t as sure of a thing as you thought he’d be. Well, you’re done. You’re out. You’re in Bristol doing Coors Light Cold Hard Facts.

But if you bring Love back for his contract year, now he’s playing for a mega-deal on a Minnesota team that underachieved last season — thanks to a ridiculously competitive conference, poor coaching from Rick Adelman (since retired) and historically bad luck in close games. Couldn’t your team blossom like the Blazers did last season? Remember when we thought LaMarcus Aldridge was fleeing Portland … right until it turned into a playoff team and made the second round? What if that’s Minnesota next season? It’s not inconceivable, right?

Trust me — Flip keeps playing that Aldridge-Portland scenario in his head. More importantly, he can’t even find a poor man’s Godfather offer for Love, much less an actual Godfather offer. (Golden State wouldn’t even pony up Thompson for him!) Flip wants no part of this generation’s one-sided “Charles Barkley for Jeff Hornacek, Andrew Lang and Tim Perry” trade that was horrible at the time and looks even more egregious 22 years later.

My guess: He’d rather keep Love for now, roll the dice with the Aldridge-Portland scenario, and then, if Minnesota starts off slow, he can always deal him before February’s deadline.

That brings me to the third thing I’d bring to Gilbert’s attention: You know who else doesn’t need to make a move right away? The Cleveland Cavaliers! What’s the rush? Why do we have to finish our roster in July? What’s wrong with riding out the current nucleus for a few months, getting everyone in a training camp with LeBron, then seeing how everyone meshes with him?

What if Wiggins shows signs — day after day after day — of becoming the Pippen to LeBron’s MJ? What if LeBron is throwing him crazy alley-oops left and right and gushing, “I’ve always wanted to play with a freak athlete like this”?

What if Wiggins and LeBron are roaming around defensively like coyotes, stripping dudes at midcourt, jumping passing lanes and basically looking like mid-1990s Pippen and MJ reincarnated?

What if sending Wiggins to Playing With LeBron Camp turned out to be the greatest thing that ever happened to Andrew Wiggins? What if this single-handedly altered his professional destiny? What if LeBron turned him into his basketball clone, much like Jordan brainwashed Pippen into evolving into his perfect sidekick?

Here’s the point: THE CAVALIERS HAVE TO FIND OUT. And they’ll know, or at least have a really good idea, by December or January.

And guess what. That same Wiggins-for-Love deal will still be sitting there after Christmas. None of the other 28 teams are trumping it. If it has to be done, then it has to be done — the Cavs can’t waste the rest of LeBron’s prime if Wiggins isn’t close to being ready yet, not with LeBron passing 40,000 career minutes during the first quarter of his first 2014 Cavs game. There’s a shelf life here. The Cavaliers can’t take their sweet time and wait for their supporting cast to catch up with the greatest player of his generation. They can’t.

At the same time, I need to see LeBron and the young’uns for a few months before I swing a mega-deal. I want to see how Kyrie Irving and Wiggins blend with LeBron — if they figure out how to run with him, space the floor for him, ease some of his playmaking burden and let HIM be the guy taking advantage of everyone else’s young legs for once. I want to see if Dion Waiters can become this generation’s Vinnie Johnson, a.k.a. Microwave 2.0. I want to see if Anderson Varejao can stay healthy for the first time since 1975, and I want to see if Tristan Thompson and Anthony Bennett jump a level because they’re suddenly playing with one of the league’s best passers.

I mean … is it OK that I see this for 45 to 50 games? Is that fine with everyone?

Best-case scenario: Wiggins proves to be untouchable and Bennett shows signs of becoming a late bloomer/belated keeper, followed by Flip begrudgingly settling for a February deal of Love for Bennett, Waiters, two unprotected first-round picks (including Miami’s first-rounder that’s unprotected in 2017) and one pick swap over the next five years … a deal that, by the way, is still better than any other offer they’ll get. Yes, including the right to overpay David Lee and eventually overpay Klay Thompson.

Worst-case scenario: Wiggins suffers enough growing pains that you no longer feel fearful or guilty about flipping him for Love in February … which means Cleveland would be trotting out one of the seven best basketball players of all time and one of the league’s 12 best players as his sidekick.

In summary, the Cavaliers can’t lose no matter what happens. I look forward to them screwing up the final decision and somehow having it work out. In Gilbert We Trust.

Here’s what the other Grantlanders think …

Chuck Klosterman: If you deal Wiggins for Love, you obviously have the best team in the East. You obviously have the ability to spread the floor and outscore everyone, and the premise of Love throwing full-court outlet passes to Irving and LBJ would make all of November feel like a McDonald’s All American Game.

These are the obvious details everyone will mention when considering this hypothetical. But I would still stick with Wiggins, and my reasons are threefold:

1. I am not totally convinced Love is much more than an incredibly skilled fantasy player. He certainly might be, but how could we possibly know (based on experience)? Such a move would still be a gamble. He doesn’t protect the rim. He seems inordinately interested in numbers. And those aforementioned full-court outlet passes evaporate in June.

2. Up until the Big 12 tournament, Uncle Wiggily was pretty underwhelming at Kansas. He had a few games in which his shooting was tragic, especially off the dribble. But he has the body, and that’s what matters. His body is better than Love’s. He defends the whole floor. He’s an underrated glass chewer. And if we all concede that Wiggins has the potential to be a transcendent player, placing him alongside a bike-riding maniac like LeBron is the best-case scenario. If you throw 20-year-old W with LBJ, you will get the totality of whatever he has to offer (and then you re-sign him for life). LeBron will not let him bust.

3. The Cavs signed LeBron. He’s the best player in the world. Let him prove it. Enough of this pandering. No more roster additions. No more gaming the system to make things easier. This is the team. Play with this team. That letter James “wrote” to SI? Idiotic. It was totally idiotic. I’m not interested in constructed apologies or histrionic aphorisms. Just go do this.

Mark Titus: “Should Cleveland give up a guy who has the potential to be one of the top five players on the planet in seven years for a guy who hasn’t made the playoffs in his six-year career? Before you answer, consider that the guy for whom Cleveland is trading is reportedly going to bolt his team in free agency next season if he isn’t traded, meaning Cleveland holds pretty much all the bargaining chips here.”

Um, no?

That the Cavs ever considered this trade as a possibility tells you how insecure the Cleveland sports scene is. It’s like as soon as LeBron announced his decision to return, Kool & the Gang was blasted through the entire city on loop as Clevelanders danced in the streets and Frenched strangers. Then, after a few days of this, someone tapped Cleveland on the shoulder and told it LeBron signed only a two-year deal that includes a player option after the first year. Even though it’s fairly obvious that LeBron’s deal was structured in anticipation of a projected salary cap rise, the music was still cut as every Clevelander went through the same mental anguish.

Oh god, oh god, oh god. OK, don’t panic. We’ve got this. He’s not going to leave again. He can’t. There’s no way he does that to us twice. Is there? Shit, there is. He’s going to do it. He’s going to leave again, isn’t he? He’s probably already got one foot out the door. Well, if that’s how it’s got to be, let’s just go all in and win a title this year so at least we have something to keep us happy when he rips our hearts out a second time.

Don’t get me wrong here — the Cavs should be making moves to win now. LeBron + Anderson Varejao + Brendan Haywood + guys who haven’t hit puberty yet doesn’t strike me as an immediate championship formula. But taking a few young pieces out of the mix and throwing in Love suddenly turns the Cavs into the obvious choice for Eastern Conference champions. So I’m all for going after Love.

I’m just not for giving up Wiggins. A lot of people seem to misunderstand the talk surrounding Wiggins and assume that because he’s described as a guy with a ton of potential, he must therefore be a gamble. But just because his ceiling is so high doesn’t mean his cellar is just as low. In truth, even if Wiggins never asserts himself offensively as consistently as he should, he’s still likely going to be a 15-plus PPG guy and one of the best perimeter defenders in the league.

That last bit is huge. The Cavs are in a great spot as it stands by having a young guy who can help LeBron carry the offensive load (Irving) and another who can help carry the defensive load (Wiggins). Wiggins on the Cavs means LeBron won’t always have to guard the other team’s best player. It also means Cleveland could conceivably have the two best perimeter defenders in the game three years from now. That might not sound as sexy as a 26-and-12 guy joining LeBron, until you realize that a Cavs defense with Wiggins and LeBron will get infinity steals, those steals will trigger fast breaks, and those fast breaks will end with one of those guys putting his nuts above the rim.

Throw anything else at Minnesota to get Kevin Love to Cleveland. Just don’t touch LeBron, Irving, or Wiggins.

netw3rk: Rationally speaking, you can’t really argue for not trading Andrew Wiggins for Kevin Love. Critiques of Love’s game often revolve around the dearth of playoff appearances and his being a stat-stuffer. My retort would be that, if the 2013-14 Timberwolves were in the Eastern Conference, they surely would have made the postseason. And even if he is a stats hog, holy shit, look at those stats!

Last season, Love scored 2,010 points, pulled down 963 rebounds, and dished out 341 assists.

The list of players who have scored more than 2,000 points, grabbed more than 950 rebounds, and dished more than 300 assists in one season is as follows: Kareem six times (1969-70, 1971-72, 1972-73, 1973-74, 1975-76, 1976-77), Wilt Chamberlain twice (1963-64, 1965-66), Elgin Baylor twice (1960-61, 1962-63), Oscar Robertson (1961-62), Bob McAdoo (1975-76), Billy Cunningham (1969-70), Charles Barkley (1988-89), and Tim Duncan (2001-02). I’d call that good company.

Wiggins is a very talented, ultra-athletic incoming rook who has a great chance to be a defensive destroyer and a star. He doesn’t need the ball, and that’s a plus on a team with Kyrie, LeBron, and (for now?) Waiters. But, again, Love is coming off a historically good season.

Still, I think it’s more instructive to turn the question around. If I were a fan of the Timberwolves, and Flip Saunders sent Love to Cleveland without getting Wiggins in return, I’d storm the Wolves’ practice facility and burn it to the ground.

Andrew Sharp: Is Daryl Morey secretly overrated? Who’s had the better career, Tom Hanks or Tom Cruise? Jay Z or Kanye? Should you let your kids play football? Would we all be better off if the Internet didn’t exist? Has Barack Obama’s presidency been successful? These are debates. Reasonable people can argue both sides.

Was David Kahn secretly underrated? J. Cole or Kanye? Is that bookcase talking to you right now? Should Barack Obama be arrested for treason? These are not debates.

It’s not a debate if one side of the argument is just crazy people.

That’s how I feel about the “Should the Cavs trade Wiggins for Love?” question. If we talk about it long enough it may seem like a real question, but this should never get that far.

As good as everyone hopes Wiggins will be one day, Love is that good right now. I understand that playing with LeBron gives Wiggins a much better chance of maxing out all of his potential, and it’s something everyone wants to see. I even understand the people who think Wiggins could help extend LeBron’s prime the way Kawhi Leonard did with Tim Duncan. But let’s not be crazy.

There’s no way Minnesota’s doing a deal with Cleveland that doesn’t include Wiggins, and if that’s the case, the Cavs absolutely have to include Wiggins and get the deal done.

LeBron’s 29 years old. The East is wide open. Even if you think Wiggins will be a star — I think he will — it probably won’t happen for another three or four years, at which point the East will probably be tougher, LeBron will be older, and there’s a chance the Cavs will have wasted three years of LeBron with no titles, while the entire city of Cleveland gets a little more anxious every year.

Why make it complicated? Don’t give the Warriors a chance to come to their senses and offer Thompson. Love and LeBron would be diabolical right this second. The passing alone would make them the most entertaining team on earth. They wouldn’t even need three other players. Just let them run a two-man weave on the entire league.

Think about it this way: What do other teams want the Cavs to do? Teams could take their chances the next few years against LeBron and Kyrie with a bunch of young guys and broken-down veterans trying to fill in the gaps around them. Or they could spend the next five years facing a new superteam with Love, LeBron, and Kyrie, three superstars smack in the middle of their primes, with less pressure on the young guys and a new cast of veterans signing on every summer. I’m sure it’s tough for Cleveland fans to watch Vines like this and imagine that player somewhere else, but come on. Don’t overthink this. The biggest reason the Cavs should trade Wiggins for Love is because every team in the league is quietly praying they’re crazy enough not to.

Illustration by Muideen Ogunmola