Entering a second straight NBA winter with more teams looking to upgrade their rosters rather than selling off valuable veterans, no rival front office may be monitoring the sputtering Chicago Bulls’ decision-making closer than that of the Orlando Magic.

It was this time two years ago league executives were circling Orlando as the trade deadline approached, and the Magic delivered: dispensing Nikola Vucevic, Aaron Gordon and Evan Fournier across the postseason map.

The ramifications of that Vucevic deal lie at the center of Chicago’s current predicament. Forget the fact talent evaluators are consistently pegging Wendell Carter Jr., the centerpiece of the Bulls’ package that landed Vucevic, as a more impactful player at present than the veteran center. The first of two picks Chicago sent to Orlando already netted dynamic wing creator Franz Wagner in the 2021 NBA draft. The second outgoing Bulls pick to the Magic is this year’s top-five projected selection that’s protected only Nos. 1-4 — which could bring Orlando a second premium lottery selection in a highly anticipated draft class.

A six-game winning streak that ended Monday, Paolo Banchero’s stellar rookie season, plus Orlando’s unique blend of size and young talent has onlookers rather bullish about the near future of these Magic. They are not exactly banging down the door of the play-in tournament, but Orlando, at 11-21, has exhibited the positive step toward competitiveness that Magic staffers were hoping to witness this season.

“They have two of the premier positions in the league — playmaking forwards — on rookie-scale contracts, intriguing young talent around them on solid contracts, no bad money moving forward, and some veterans who could get them back even more draft capital should they choose to trade them,” one Eastern Conference team strategist told Yahoo Sports.

There are certainly pieces for Orlando to move ahead of this season’s deadline, but the Magic won’t be gaining nearly the return they saw two years before.

Terrence Ross has long garnered interest from the Los Angeles Lakers, sources said. New York was in pursuit of Ross in previous years, as well. Yet, while Orlando has rebuffed offers below a first-round pick for the veteran swingman in recent seasons, sources said, it’s difficult to foresee a playoff contender sacrificing more than a single second-round selection for Ross’ services. The same goes for Gary Harris, although both wing players carry no guaranteed salary beyond this 2022-23 campaign.

R.J. Hampton is another strong Orlando trade candidate after the Magic didn’t pick up his fourth-year option for next season. Hampton has changed representation and searched for more playing time with Orlando’s G League affiliate in Lakeland, Florida, but he is also unlikely to draw a significant yield.

Former No. 6 overall pick Mo Bamba may be the Magic’s greatest trade chip. Orlando pursued Isaiah Hartenstein in free agency, sources said, before the center joined New York and the Magic then re-signed Bamba to a two-year, $20.6 million deal. League executives expect Orlando to hold out for a protected first-round selection or a late first-round pick to part with the 24-year-old rim presence. There are teams like the Lakers and Clippers, as well as Toronto, Sacramento and Brooklyn, that front-office personnel expect to sniff around the big-man market ahead of the Feb. 9 trade deadline and may be willing to cough up a pair of second-round choices for Bamba. Chicago, too, has been considering its post-Vucevic options as his contract comes to a close at season’s end.

All this is to say whatever in-season tinkering comes from Orlando may be more predicated on amplifying that bright horizon rival personnel believe is coming.

If the Magic keep their entire roster for next season outside of Harris’ non-guaranteed 2023-24 salary, they’ll be playing with roughly $37 million in cap space. And there are direct avenues for Orlando to clear upward of $60 million this summer. Markelle Fultz is on the books for only $2 million guaranteed next season. Bamba’s second year is completely non-guaranteed as well. Bol Bol has a non-guaranteed salary for 2023-24. And that’s not to mention Jonathan Isaac’s deal that can cost Orlando precisely nothing beyond this season if the Magic choose to part ways with the injury-plagued defensive stalwart.

If you’re sensing a theme, it’s quite apparent how significantly the Magic value financial flexibility amid this rebuild. And you don’t just keep your books clean for the sake of monetary tidiness in perpetuity. League figures familiar with Orlando’s thinking maintain Magic ownership will be ready to spend when the opportune time arrives to support Banchero and Wagner.

Will that come this summer? Or would the Magic pounce on an upcoming free agent before the deadline to obtain that player’s Bird rights or simply begin incorporating him into the flexible lineups at head coach Jamahl Mosley’s disposal?

“Everyone talks about playing positionless basketball,” one scout told Yahoo Sports, “but they’re the only ones who have really said, ‘F*** it.’”

With Orlando’s pair of supersized ball handlers, guard play isn’t necessarily a dire need for the Magic. Plus, Fultz has shown continued promise in 11 games this season, converting over 40% from distance while sporting an increased comfort shooting off the dribble.

Still, the Magic’s backcourt is an obvious area for Orlando to look to spend. Especially in advance of Cole Anthony’s rookie extension conversations next summer, for which league personnel are preparing for a sizable gap between Anthony’s wishes and his ultimate market value. Perhaps we’ll gain a further glimpse of the Magic’s plans if they entertain moving Anthony before the deadline.

It is too early to pinpoint specific Orlando targets should the Magic grow aggressive between now and the opening night of next season. But scan the list of upcoming free agents and take your pick to who’d best slot alongside the Magic’s core pieces.

Could you fault the Magic for throwing maximum money at, say, Khris Middleton, who holds a player option for next season and whom Magic general manager John Hammond landed for Milwaukee when he was piloting the Bucks?

Here’s to waiting and seeing if this current Orlando regime is willing to take a big swing.