I think there's a plausible argument that Bogaerts would have stayed with the Sox for the 6/162 he was finally offered by them, if they went to him around the time Story was signed.
The main reason I think this is Story's contract of 6/140. When we signed Story we did some statistical comparisons, and Story was just slightly behind Bogaerts in fWAR per games played. Very close. A 6/162 offer would have represented 15% more than Story got.
Also, even though Boras was Bogey's agent, Bogey's previous extension was clearly a team-friendly one.
Finally, Bogey seemed to really like playing for the Sox.
No one will ever know if the 6/162 would have gotten it done, but at the time that would have been a very legit offer.
The contract Bogey got was quite possibly the most bonkers contract ever handed out. It was just pure happenstance, I think. Just look at what happened with the other big Boras clients this past offseason.
When it's all said and done, the Sox are probably better off they didn't retain Bogey. Out of the big 3, it was Betts and Devers they really needed to keep.