Detroit Rationale
Hardaway's contract is expiring. If he isn't going to get an extension in Detroit, and they want someone who can fill his role, Simons might be a great fit. He is almost a perfect statistical clone of Hardaway with slightly better career shooting and assists, but slightly worse defense.
Simons's career history suggests he's more likely to flourish offensively in a secondary role like Hardaway's than as a primary ball handler, though it's a nice bonus that he gives you depth at secondary ball handler.
One snag could be the fact that Simons' numbers are way down so far this year. Some in Blazers' media feel it's due to a lack of adequate help on Portland's shooter-deprived roster, leading to defenses focusing on Simons. Others have cited Portland's stagnant ISO offense as not creating enough open looks. Sounds like excuses, so I'd expect Detroit to want to see Simons exit the slump before a trade is signed.
Portland Rationale
Trading Simons is a top priority for Portland. Their rebuild needs picks. Freeing up some cap and a roster slot with Hardaway's expiring deal supports their rebuilding mission also.
Maybe saving the salary can also allow the Blazers to:
lower ticket prices to get more fans into the building than 50% capacity
reopen the 300-level concession stands at the Moda center
buy some extra metal detectors so it takes less than 30 minutes for fans to get into the arena if their keys set off the cheap detectors
turn on the heaters in the building so it's not freezing cold
Because right now that place is a ghost town that feels like entering Albania.
And maybe, just maybe, Hardaway Jr. gives Chauncey that extra vet presence on the team to help catalyse some better efforts than what we saw in the 45-point loss to Memphis.