The Padres, determined to improve their moribund offense, were so enamored by Sandoval that they actually offered more money -- not average annual value, but in excess of $100 million -- to land him, making him the first piece to their offseason rebuilding plan.
That collective groan on Nov. 25, when Sandoval pulled on a white Red Sox jersey at a news conference at Fenway Park, was from the Padres fan base, one left skeptical and hurt, even if there was debate if Sandoval was the right fit to begin with.
But if Preller and his front-office staff viewed this as a setback -- or the Yasmany Tomas deal with the D-backs, another target, though one not pursued as ardently -- it certainly didn't last long.
"You've got to be prepared to move on to Plan B, C, D or F or Z. We don't have a [front-office] group that dwells on things too long," Preller said. "We want players that want to be here, and if it didn't work out, then we'd go to the next thing and try to get better."
Watching all this was Padres executive chairman Ron Fowler. If he wasn't already impressed with how Preller handled himself, watching him shift gears after being rebuffed by Sandoval was something akin to front office poetry in motion.
"When we went after Pablo, we were all in," Fowler said. "When it didn't work out, A.J. decided to take a step back and say, 'Let's see what we can do in the trade market.'"
That's essentially the time when Preller, having never done this job before, cast a wide net out among teams as he looked for potential offensive upgrades for the Friars' roster. He wasn't position specific. You say that the team has too many outfielders? If outfielder was where he could -- and, ultimately, did -- get the most bang-for-his-buck, he would pursue it.
"He was working four or five deals at a time," Fowler said. "With A.J., it's never say never. He'll find a way to get something done. It's fun to watch and listen to and see his thought process work."
First, there was the deal for Dodgers outfielder Matt Kemp, one that was discussed between the two teams for weeks before it was consummated at the Winter Meetings in early December and officially announced on Dec. 18 -- the same day the Padres traded for A's catcher Derek Norris.
The Kemp deal was notable on several fronts, most notably that the Dodgers agreed to front-load $18 million of the remaining $32 million on Kemp's contract, which gave the Padres some additional flexibility in terms of payroll for 2015.
"Previous Padres, I would say, if you were able to get Kemp, you take a deep breath and say that you're doing pretty well," Fowler said. "Not this guy. When the Dodgers front-loaded the deal, we had some money to work with. A.J. said, 'Let's go after [Justin] Upton.'"
A day later, Preller obtained Upton from the Braves in a six-player deal, giving the Padres a major facelift in the outfield -- Upton in left, Wil Myers, from another deal with the Rays, in center field, and Kemp in right. It also, at least on paper, inspired hope that the offense won't be the worst in baseball in 2015 as it was a year ago.
So what if the Padres had signed Sandoval, Tomas or any of the other free-agent targets they considered or offered? How would that have changed the landscape of their offseason, their roster?
Preller smiled. It's a question that can't easily be answered.
"Each decision takes you down a slightly different path," Preller said. "If it was Sandoval or any of the other things we discussed, it would have been a different path, but in general, we were trying to go down a few [paths] to try and make the team look better. If we had signed Pablo, it would have changed our course a little bit. That's just the nature of the offseason."
One that has, so far at least, gone swimmingly for the Padres -- even if it started abruptly when Sandoval opted to head elsewhere.
"Did we think that all these things could happen? We thought some of them could," Fowler said of the many moves this winter. "But A.J., in the back of his mind, might have been the only one who thought we could do all of these things."