I believe we are one blockbuster deal away from legit contention status. Hopefully, we have the assets to make it work. After all, we got all our future firsts intact. Off the top of my head, three potential targets come to mind: Simmons, Beal, Siakam
For what they would likely cost and fit on the roster Siakam makes the most sense of those 3. I'm not sure we have enough though for any of them without including Brown and that doesn't make sense. We'd need a 3rd team to take some of our vets and provide young players to Toronto. So like if we could Wiseman for Smart (or something like that).
So in January, maybe something like this
Boston - Siakam, Dragic, Looney
Golden St. - Smart, G. Williams, Horford
Toronto - Wiggins, Wiseman, Langford, Nesmith, Bos 22 1st, Bos 24 1st
Something like that, but we'd also have to trade Horford but at least he'd go to a contender in that scenario (Warriors would save cash and get another versatile wing defender and a real option at center).
So post-trade
Starters - Dragic, Brown, Tatum, Siakam, R. Williams
Rotation - Schroder, Pritchard, Richardson, Parker, Kanter, Looney
Deep Bench - Hernangomez, Fernando
I like how that roster shakes out both for the rest of year and long term a lot better as you have a nice young big 3 with RW as a long term center and PP as potential long term PG. Over the summer, ideally you'd keep Dragic or Schroder (if not both), but it provides some options there.
I'd do that trade for the Celtics.
- Siakam is an all-star-caliber player. I reckon he'd be an elite glue guy alongside the Jays. He's happy to play off the ball in the half court. He's a terrific option in the open court. He's also a great defender.
- Dragic is a battle-hardened vet who thrives in the half court. He'd help us a lot, especially in the playoffs. Unfortunately, he's overpaid, but his contract expires at the end of the season. Looney ain't no scrub either. He's a serviceable small ball Center.
- Horford is a very useful player, but he's massively overpaid. Chances are he has negative trade value.
- Nesmith cannot put the ball on the floor, which means he cannot create his own shot. He projects to become a role player.
- Romeo is a (very) poor man's Jaylen. I'm fine parting ways with him, given that we got the original Jaylen. Fwiw, we also got a poor man's Romeo in Begarin.
- Grant Williams is pretty much a nonfactor for me. We can easily replace him.
- The 2 firsts will likely be in the 20s.
- I'm relatively OK with trading Smart too, especially since he signed a hefty contract extension. In any case, you gotta give up something to gain something else. That's how trades work.
With all that said, my #1 target would be Ben Simmons.
- His value has hit rock bottom. We should always try to buy low and sell high.
- Basketball-wise, I absolutely love the fit alongside the Jays.
- He perfectly fits our time window.
(click on image to enlarge)

Smart cannot be traded till January 20. Schroder cannot be traded till December 14.