Some interesting hot political takes in here. I won't get too off topic but with my post. Ultimately there's no "real" job that suits Masai's vague interests.
1. Philanthropy? I could see him forming another charity and making that his top priority but that's typically a side project for someone - i.e. Jalen Rose school, LeBron James "I Promise" program, Obama "Brother's Keeper" program. Neither of those folk run the project fulltime. To a degree the Bill and Melinda Gates foundation is somewhat similar. Even if he worked with the UN I'm not sure if that's his skillset - he already does the NBA Africa program (or helps it out), there's not much value in doing something with the UN brand. I do see him having an interest in bringing COVID vaccines to Africa and just the general healthcare situation. Perhaps as a partner in an overall organization but I wouldn't pin him as the guy willing to do it from scratch. So do I see Masai just going head first into something philanthropic? Highly unlikely.
2. Politics? No. At least not formal politics like a mayor or elected official. There's multiple reasons for this. To address some takes in this thread politics rarely attracts the quote "best and brightest" talent. A lot of those personalities that are driven do so because they have a capitalist driven objective or some sort of fulfillment that drives them. With politics the act is to be an idealist and affect change, it's an act of charity. That's the idea at least - doesn't really work seeing the results. Politics are usually lawyers or etc related field due to the machine related understanding of legislation and other boring ins and outs.
No seriously - ask yourself why does a guy like Donald Trump (who is a multimillionaire by all counts) want to be president (or wanted)? It's a job that pays something like ~400k a year and most presidents donate their salary. It's because he wanted to help funnel money to his brand/name. Basically leverage political office into a $$$ situation - it's corruption. I'm sure it doesn't hurt the ego of a politician to have a legacy as well. You do need a certain megalomania to run for any political office.
In addition, with politics you lose a ton of brand control because automatically 50% of the voting population will write you off during and after your political life - impacting your perception the rest of your life. It's much easier to be "the basketball guy who helped build a team to win an NBA championship" than to be "the politician who oversaw massive delays in hospital care post covid19" (just taking a random stab at it). LeBron might be able to run for governor of Ohio as the favourite son just for the hell of it - he's already political and the people who hate him would already hate him. He also has so much money it probably doesn't matter.
Needless to say Masai probably wouldn't take the role for the same reasons millionaires and billionaires don't often seek office. It's a branding mistake for once and any financial advisor would flip out seeing the lack of 0's brought in going forward. Masai also doesn't seem corrupt enough to want the job - the machine politics are just daunting, slow and the news cycles are silly for someone of his personality.
Extreme side note: For those who want a solution and how to attract the "best and brightest talent" to politics it may seem backwards but one of the methods is to pay a lot more. Not just double. But almost triple or quadruple. Look up Singapore. There are many reasons they have low corruption - one of them is simply because salaries for their politicians are close to 1 million or more last I checked. It means people who are doctors, successful business people and etc are willing to leave their profession because they get a pay raise but also they're held to a way higher standard as a consequence. They're also less likely to take bribes because they're already being paid a high amount. There's ultimately many ways to get these types of people into politics but it requires serious reform that a lot of people will balk at ("you're asking me to give Doug Ford triple his salary???" "Trudeau never helped me why should I allow these politicians to increase their salaries! I haven't gotten a wage increase in years!").
3. Another team? Highly unlikely. The TL Seattle thing comes up every now and then. But we're years away from that happening. Possible ownership stake, fresh start - but even if we're 5 years away I don't see a 55 year old Masai Ujiri with the same passion for basketball as what he's built with the Raptors over a probable 15 years. But who knows? I could see a Lou Lamoriello situation Maple Leafs/Islanders with Masai but if I'm Tim Leiweke, the first person I kick the tires on is Sam Presti. OKC is pretty well situated with the draft but we know their ownership isn't everything. Presti is young enough and most likely won't win a championship in the next 2-3 years. You get a bunch of backers + TL + fresh start team + great market + young GM that hasn't seen much success it's a great story.
Masai though? He's won his championship. Built his legacy here. Family are basically Canadian. Not saying it's impossible for him to leave this offseason but Woj isn't wrong. It would have to be a VERY compelling offer to get him to go to say the Atlantic Hawks. He's just not a guy like David Griffin (no offense to him) - he's not starting over with another team, another coach, another staff when MLSE can likely outbid everyone and give him continuity.
Masai is extremely hard to get a read on. This entire board including myself haven't ever been able to parse through his words because he keeps his cards close. I truly don't think Masai knows what Masai wants to do. If this wasn't a covid world - I could see a situation where he leaves and joins something larger with basketball and Africa or a charity. But with travel being restricted and his kids are still very young (not even in high school yet?) - I doubt he wants to be that far away for too long. Some of this information is probably fed to drive up his price, as any agent would do for their client.
I think he stays with the Raptors for large money (don't cheap out MLSE). The years I couldn't tell you. If he leaves it's for something larger than basketball. But I really don't think Masai knows right at this moment what he wants to do at say 55 years old. 51-54? Probably continue to be with his kids and earn a lot of money with the Raptors while continuing to build your network. Pretty sweet gig if you can get it.