My initial thought after the Stevie Yzerman firing was that it was very possible, but the more I think about it, the more I wonder if it may be too far gone. 

 I predicted when Dylan asked for a trade that he would do everything he could to get to Minnesota for various reasons 

1) He and Quinn Hughes have the same agent and are very good friends. After Yzerman failed to acquire Hughes last year when he had the opportunity to I felt discussions between Quinn and Dylan would have been frequent and they also being Olympic teammates even more so.

2) Minnesota is fairly close to Michigan, where Larkin has a lot of family and with a one-hour plane ride, his wife and newborn would be able to have family close as much as possible while Larkin pursued professional goals. I do think that in most circumstances Larkin would not leave Detroit due to his love for his home state and family.

3) After what seems like has been a tumultuous relationship with Stevie Yzerman I would think that it would be of high value to Dylan and his wife that he goes to a place that has a G.M, that he has a good relationship with already and that thinks highly of him. Bill Guerin is all that. Guerin was the G.M of the Olympic team that won gold and selected Dylan over some very good players to be part of the team. I can only imagine that Dylan and his wife built a significant relationship with each other during that time and obviously Bill showed he valued Larkin quite a bit.

4) Win now. Bill Guerin showed he was willing to take risks to win now with the trade for Larkins friend Quinn Hughes whom did not formally commit long term to sign a contract with Minnesota but Guerin was willing to give up significant assets to acquire him anyways. The move signaled a very win now message that I imagine is music to Dylan's ears after hearing "Yzerplan" for his whole career

Conclusion

With all this in mind I wonder if things are to far gone for a return to Detroit for Larkin. It appears that Bill Guerin has put many things on hold in wait of Dylan's eventual arrival, including apparently passing on Trocheck in hopes of acquiring Larkin (rumor). It is possible that all of this focus to have Dylan in the fold will simply have put Larkin too far into the process to go back. The wheels might have been moved to far in that direction for a directional correction. Detroit could only hope that Dylans love or Michigan will take the reigns and move the wagon home.