Welcome to Toronto: It’s the best of times, it’s the most uncertain of times. Since the All-Star break, the Raptors are 11–5 even though Kyle Lowry has been sidelined after wrist surgery, and they’re second in defensive rating — supercharged on that end of the floor by Serge Ibaka and P.J. Tucker. DeMar DeRozan is on fire, going for 40-plus points three times since the break. To hear Raptors team president Masai Ujiri tell it earlier this month at the MIT Sloan Sports Analytics Conference, the players, “the city of Toronto, the fans, and the organization” deserve “a chance” — for a title.

Ibaka and Tucker certainly help Toronto’s chances against a wobbling Cavaliers roster. The Cavs’ defensive rating is 1.3 points worse than the league average. Since 1980, of the 74 NBA Finals participants, only one had a worse relative defensive rating (the 2000–01 Lakers), per research by NumberFire.com. If the Raptors were looking for an opening, this might be it. Ibaka and Tucker, both unrestricted free agents this summer, could turn out to be half-season rentals, but as Ujiri said, “those are the risks you take in this business.”

Ujiri said something else at Sloan that struck me. He was asked during a panel called “Beyond the Foundation: Building a Team Around a Superstar,” how long he believes this team’s window will remain open. Ujiri said that he thinks Lowry and DeRozan are superstars, so the front office owes it to them to “maybe make sacrifices.” Then he answered the question: “So, window? Heh heh. I don’t know. Could be three months. Could be three years. That’s the instinct you have to work with in our business. The fine line I work with is developing and winning. It’s sometimes difficult to do.”

On the surface, the Raptors are a feel-good story. But the past three years have ended in playoff disappointment. They lost in Game 7 in the first round at home to the Nets in 2014, then got swept in Round 1 by the Wizards in 2015. It took 14 grueling games to get by the Pacers and Heat before falling to the Cavaliers in the 2016 Eastern Conference finals. Maybe their midseason reinforcements get them over the hump, but if they don’t, the fabric of the team needs addressing. Otherwise, every year will end with maybe next year.

The Raptors will arrive at a crossroads this summer. Ibaka, Tucker, and Patterson will be unrestricted free agents. Lowry will be, too, if he declines his player option, which he plans to, according to The Vertical’s Adrian Wojnarowski.

Re-signing a three-time All-Star franchise point guard seems like a no-brainer. Lowry can demand a five-year maximum contract worth more than $200 million, but he will be 31 at the start of next season, is small, plays a relentless style, and takes on a heavy workload.

A 2009 study by Neil Paine, now with FiveThirtyEight, found that guards generally begin a rapid decline at age 32. Paine’s data supports the conventional wisdom that smaller players usually rely on speed and agility — skills that dissipate earliest. Lowry is a late bloomer who has improved over the last three seasons and was having a career-best season before his wrist injury. If he ages gracefully, like Steve Nash or Jason Kidd, he’ll beat the odds.

Related The Toronto Chemistry Experiment

If you believe that the Raptors’ current core, along with younger players including Norman Powell, Jakob Poeltl, and Bruno Caboclo, gives them a shot at the Larry O’Brien Trophy, then you should be cool with re-signing Lowry, Ibaka, and the others. But if you believe this team is below the top tier — the Clevelands, Golden States, and San Antonios — and can’t afford to stand pat as its best players naturally decline, then you might have some reservations with that approach.

The Raptors will soar into the luxury tax if they retain their pending free agents. They have a top organization, but that investment would have significant risk because the team would lose the financial flexibility to get better through free agency. Toronto isn’t a traditional landing spot for free agents, but if a player did want to go north, the Raptors would need to move valuable contributors like Jonas Valanciunas, DeMarre Carroll, and Cory Joseph to create the necessary cap space. Down the line, that space could be absorbed by Powell and Lucas Nogueira, both restricted free agents in 2018. This is why this piece is about the Raptors: They can lock themselves into an aging core, while teams like the Celtics have cap space and high-value assets to make moves, and the Bucks have a young core, and the Sixers have a combination of those advantages. The Raptors could become a treadmill playoff team like the Hawks or Clippers.

The NBA is a meritocracy. That’s not necessarily a compliment. The long regular season and demanding postseason don’t allow for Cinderellas, and title contenders tend to have the best individual talent. When Kevin Durant went to the Warriors, any basketball fan outside of Golden State saw it for what it was: a blow to league parity. At Sloan, Ujiri said, “Sometimes even a player — Kevin Durant going to Golden State — will totally change like how you think about what you are doing with your team.”

In the Eastern Conference, franchises are having an existential LeBron crisis. Until King James declines, the rest of the best in the East has to hope LeBron turns an ankle or Kyrie Irving sprains a finger. On a level playing field, against LeBron everyone else is fighting for second best.

The Raptors will want to keep recent history in mind as they head into the offseason. Think of the Pacers teams from the early part of the decade. They built an identity around defense and their revelatory two-way star, Paul George. But they hit a LeBron wall they couldn’t climb, and the league changed seemingly overnight — moving to a pace-and-space era, drunk on outside shooting and small ball. All of a sudden, Indiana became a mediocrity, and within a few seasons core players from the 2011–12 and 2012–13 teams — Danny Granger, Roy Hibbert, Lance Stephenson — were either out of the league or barely in it. The Eastern Conference is littered with franchises (the Bulls, the Hawks) that took a shot at LeBron and wound up in purgatory for their troubles.

I disagree with the idea of punting a season purely because an opponent seems invincible. We’ve already seen that the Warriors and Cavaliers are vulnerable. But team-building must be done with an eye toward sustainability, not hope. If Toronto’s 2017–18 season will be more of the same, with even less financial and asset flexibility to make impact additions, then the best future for the Raptors will come in the form of a teardown.

Ujiri is unafraid of making deals that send shockwaves through an organization. When he first arrived in Toronto, in 2013, his aim was to press the reset button. “We act like we are the smartest guys in the world, but there is a little bit of luck in this business,” Ujiri said at Sloan. “When I took the job in Toronto, we were looking to see which way we would go. At one point we were trying to trade some of these guys. … I went to Europe, honestly, and was thinking, ‘You know what, we’re going to lose so many games now and we’re going the other way.’”

After reshaping the roster by trading Andrea Bargnani and Rudy Gay, Ujiri fielded calls for Lowry. Knicks owner James Dolan famously nixed a proposed 2013 trade for Lowry because he reportedly didn’t want to be “bamboozled” again by Ujiri, who was the Nuggets’ general manager at the time of the 2011 Carmelo Anthony trade.

The Raptors were unable to find a team that’d give up a young player and a first-rounder for Lowry. A league source told me that the Warriors were unwilling to include Festus Ezeli with a pick for the point guard, which shows where his value was at the time.

A funny thing happened next: Lowry became the face of the team, the Raptors won 48 games, and they made the playoffs by accident. It wasn’t Ujiri’s original plan to build a title contender, but it’s not the worst hand to be dealt.

The idea of signing and then dealing Lowry down the road might seem absurd, but don’t put it past Ujiri. When the lockout-shortened season began in December 2011, the Nuggets re-signed Nene and Arron Afflalo. Nene was swapped for JaVale McGee in March 2012 and Afflalo was part of a trade that brought Andre Iguodala to Denver in August 2012.

There was backlash against the Nene trade. CBS Sports’ Ken Berger reported the Nuggets felt “buyer’s remorse,” and USA Today’s Sam Amick tweeted that the Nuggets began working on Nene trades not long after re-signing him. Trading a player so quickly after committing to him is not unprecedented, but it’s rare. Back then, Nuggets president Josh Kroenke said it was never their intention to trade Nene, but with the team performing underwhelmingly, circumstances changed and “things came to fruition literally five minutes before the deadline.”

Ujiri has made big moves, regardless of how they might be perceived. Re-signing Lowry and Ibaka allows the Raps to make another run next season. But if rebuilding or retooling is on Masai’s mind, it’s doubly important to bring them back to retain the chance for a delayed sign-and-trade. He could always deal them shortly after they sign.

If Ujiri really wants to shake things up, he could look into parting with his other superstar.

Lowry is older than DeRozan, and conventional wisdom would suggest hanging on to the younger of the two stars. But over the last three postseasons, the Raptors perform better when Lowry is on the floor without DeRozan. There are variables, such as opponents’ lineups and game situations, that play a role in that net rating differential, but it’s been a consistent-enough trend that we can safely say the Raptors’ postseason offense sputters with just DeRozan on the floor. Here’s the data, via NBA Wowy:

The same was true during the regular season until Lowry’s recent 16-game absence. The Raptors and DeRozan are balling. But his scoring efficiency is still subpar, with 48.6 effective field goal and 56 true shooting percentages, per NBA.com. “We don’t play the prettiest of basketball sometimes,” Ujiri said. “We play nonconventional with shooting [a low frequency of] 3s and all that, but we try to figure out a way to build around [DeMar] with Kyle.”

Lowry and DeRozan are close friends, and dealing one could potentially anger the other — especially if Lowry inks an extension this summer with the expectation that he’ll be playing with his BFF. A full rebuild, rather than a half measure, would be a better approach.

Aside from the chemistry issues inherent in trading Lowry or DeRozan, there’s also the issue of the buyer’s market: It might be kind of cold. Most squads are emphasizing 3-point shooting, so DeRozan would make for an awkward fit in many progressive offenses. And there’s a surplus of high-level point guards right now, so paying an aging Lowry isn’t as attractive as you might think. Teams that play an old-school style like the Wolves, or franchises desperate for competence like the Magic, might make sense for DeRozan. Or maybe Magic Johnson sees DeMar as the new Kobe, and would be willing to put some of L.A.’s assets on the table. The 76ers could cough up assets for the hometown kid Lowry. When Sixers general manager Bryan Colangelo was in charge of Toronto, he was the one who brought Lowry north in the first place. All these deals feel like reaches, though.

I know what you’re thinking: It’s weird to speculate about whether a conference power should trade one or both of its franchise cornerstones during the home stretch of a fourth consecutive successful season. But that’s the strange reality of the NBA. If a general manager’s goal is to win titles and not just accumulate regular-season wins and kinda-sorta-maybe have a chance in the playoffs, then they have to constantly question their roster, no matter how good things are in the moment.

Ujiri has straddled the line between winning and development in Toronto. The big moves for Ibaka and Tucker didn’t require him to push all his chips to the middle of the table. The Raptors still retain all their future firsts, including one in 2017. They also have eight players younger than 25, with a handful of them playing for Raptors 905 — the D-League’s best team. “We have taken this unique path of maybe trying to develop players as we try to win, too,” Ujiri said at Sloan, later adding, “I feel strongly about developing players. … We talk about how you find these superstars; I think with the new CBA it’s going to be incredibly more difficult to trade for them. In many ways, we need to think about ways to find these guys.”

Timing a team’s rise is the hardest thing an NBA front office can do. But if there were ever a time to trade a superstar for a high lottery pick, it’s now. The top 10 in 2017 is loaded, and the 2018 draft is stacked up top, too, with the likes of Michael Porter Jr., Luka Doncic, and DeAndre Ayton likely to be part of the pool. As LeBron ages, there will be a new era of stars who dominate the league. The teams led by those players could be the alphas everyone else is chasing.

What’s transpired in Toronto over the past four years has been exhilarating for the city and the franchise. If the Raptors go to the Finals, expect no major roster changes. But the odds are not in their favor. LeBron is a roadblock, and a final boss awaits in the West. If the Raptors suffer another early playoff exit, Ujiri’s past suggests he will reshape the team’s future.