The game has radically changed since then and blue chip prospects are more valuable than ever. The Adam Eaton deal is a poor comp for a Reynolds trade.
Regardless, two top 75 prospects is not worth the same as Montgomery & Vaughn. Teams aren’t stupid. Andrew was a top 20 prospect who was rushed like crazy and played out of position by a desperately dumb organization. This same kid had a 125 wRC+ through August of last year despite the worst hitting coach in baseball playing up his worst tendencies and before his legs wore out from playing the OF. Every intelligent organization would die to acquire him and watch him develop into a 140 wRC+ hitter. He’s worth considerably more than you think he is despite only four years of control.
And conveniently you use the MLB.com rankings for Montgomery and not Baseball America’s, who have him as the #35 overall prospect. The difference between the #35 prospect and a guy in the 60’s or 70’s is massive. And guys like Montgomery, especially of the positional variety, don’t get moved very often in this day and age. He is the type of centerpiece prospect that would get the Pirates’ attention and one very clubs would be willing to match. Honestly, I’m doubtful the Sox would even consider moving him.
I truly believe something like Montgomery, Ramos, & Vera would be incredibly tempting to the Pirates and I’m not sure many teams would actually want to pay a steeper price than that.