If there was even a remote plan in place that had us being legitimately in on Hamilton, you don't go out and sign Victorino. On top of that, you especially don't go out and sign BOTH Victorino and Gomes. Period. It's really just that simple imo.
Except that (a) they reportedly offered Ellsbury for Lee, meaning they would have been fine putting Victorino in CF, Hamilton in RF and Gomes & Nava/Kalish in LF, and (b) you can still have an outfield of Hamilton, Ellsbury and Victorino with Gomes as the 4th OF. (Since we would have 3 starting OFs capable of starting at CF, the outfield could be shuffled with the players who are not getting a day off moving out of LF so Gomes could play there.)
Free agency not offering up the best pool of talent to pick and choose from? Go with the internal arms already in house, and wait to spend your money latter if/when something better comes along. That will always, and i mean 99% of the time always, end up trumping the supporting logic behind handing out bad "filler" contracts when all is said and done.
A few weeks ago on D&C, Lucchino said that the plan is to build "deep depth." You don't do that by filling out your rotation with your guys in the high minors who aren't yet ready to come up permanently but who you can use to call up in the event of injury (De La Rosa, Barnes, etc.), or by penciling in Morales and
Doubront-- 2 guys who have not come even close to pitching 200 innings in a single season, and then expecting Lackey to be back to LAA Lackey. In addition to that, you don't depend on 30 starts out of two
pitchers (De La Rosa, Lackey) coming off of TJ surgery, nor do you put De La Rosa in the rotation in April and expect that come September he won't be out of gas. And of course, the guy you'd call up in September to replace De La Rosa with would be... oh yeah, De La Rosa.
To build "deep depth," you stash as many guys as you can in AAA (with mL FA deals or your own prospects), you stash a guy or 2 in the bullpen who you can stretch out if need be (Morales, Aceves), and you acquire a "filler" contract (ideally, not a "bad 'filler' contract") so that the guy who in your scenario is part of the front line of defense is now your 2nd or 3rd option in the event of emergency.
"If/when something better comes along," said player is almost certain to cost way too much in prospects during the season when many teams are bidding for his services in a league which has lowered the bar for reaching the playoffs by adding 2 more wild cards, meaning the 95-win mark is too high of a target. So it is a question of shelling out only cash in the offseason versus using prospects in the season, and especially given this particular organization's situation, that seems to be a no-brainer.