The Rockies don't always have great timing when it comes to optimizing trade value. That's not easy, but often they hold onto guys too long to see their worth erode -- and sometimes teams make hasty decisions and give up a player too soon.
Now might be the time for Holliday to be dealt. As a fan, I actually would like to see them pick up another inexpensive starter to help this team finish out the year and give these guys another shot at late-season heroics since they've gotten some new life recently, but the way things are developing now makes me think that this might be the best time to get the most for Holliday if they are going to end up trading him anyway this winter. The less time he would have with a trade partner (if dealt this winter or especially next July), the lower his value may go. Right now he can help someone like the Red Sox with two playoff chases at least. Beyond that, the opportunities seem to be shrinking.
The Angels, Red Sox, and Yankees are teams that often pop-up in Holliday discussions for future deals because of their resources and use for a big bat in pennant runs. There are other teams too obviously where he could ultimately go (including staying right here as fans cross their fingers), but some of those windows might be closing a bit today.
If Boston moves Manny and gets a replacement OFer today, that might take the most likely destination out for us (although last word was that the proposed 3-way was dead). Other than the two front offices squabbling in the past, Holliday to the Red Sox next year as they replace Manny makes a lot of sense with the BoSox having some young players the Rockies would like and saw some of them first-hand in the Series as they helped bring us down.
If Bay became a Red Sox to finish out the year, maybe Holliday still works his way to Boston this off-season with Bay coming to us as he would not cost as much and be something of a reasonable replacement the franchise could use for justification. But Boston may get their long-term Manny replacement already today if he’s traded as both sides want there and not be in the Holliday bidding next winter.
The Yankees are always a possibility for great players who are going to get great contracts as they can afford it more than most. However, they are shifting away from dealing prospects, and more likely to go out and sign CC Sabathia for their big splash instead of giving up a ton of prospects and cash for Holliday.
The Angels recently got their big bat that was missing in Mark Teixeira, and I think probably make a long-term commitment there -- especially if things go well this October for them together. Maybe they go after Holliday next winter too, but adding a Teixeira isn't really their style and they are more careful with their prospects in that respect. I don't know that they would give Teixeira a monster deal and follow that right up with doing the same for Holliday at a great prospect/contract price. Teixeira might be their big dollar addition to the lineup for now.
So the Rockies might be well advised to jump in and try to replace the Pirates in that discussed 3-way deal that would send Manny to Florida and Bay possibly to the Red Sox. Surely Holliday would do a better job for them in replacing Manny's production and be a bigger long-term fixture. The Rockies could get themselves 3-4 talented prospects, many of whom might even be ready to help now or next season.
Hermida would be a solid young MLB OF replacement with some potential still who could be part of the core here if/when healthy. SP Ryan Tucker and/or OF Michael Stanton could be other possibilities from the Fish along with seeing if we could get an Ellsbury (since he's down a bit this year and fans would love to see on the other side from the Series) or young pitching prospects from the BoSox for an MVP type bat in the prime of his career.
So I think now might be the best time to sneak into that deal and get the most for Holliday before we find out we waited too long again. However, maybe it wouldn't be so bad to wait if the Rockies never find what they are looking for in a Holliday deal and just bite the bullet to sign him otherwise. That would make a lot of fans happy. For me personally, I think they can find offense overall here without creating another Helton-type deal that may hurt us down the road and would rather see that spread around a bit. If they also think that or are convinced that they can't sign him, then they ought to give the Red Sox and Marlins a call about replacing the hesitant Pirates and getting their load of youngsters now while they are to be had before it might be too late.