5 Questions -- 3. Money well spent?

The third of a five-part series looking at the biggest questions facing the Red Sox leading into spring training:

3. Was all that money wisely spent?

The Red Sox, it was widely agreed last August, were given a historic opportunity to remake their team when they unloaded $262 million in salary to the Los Angeles Dodgers (actually, closer to $250 million, since the Sox also agreed to give the Dodgers $11.7 million for the privilege of unloading Adrian Gonzalez, Carl Crawford, Josh Beckett and Shredder Punto).

So, you can understand the skeptics who look at the signings Red Sox general manager Ben Cherington has made with a good portion of that money they saved -- $107.5 million on eight players, all of whom will be 30 or older come May, average age of 33 -- and snort that this is historic only in the sense that these players will be history sooner than later.

Outside of closer Joel Hanrahan, 31, who is coming off back-to-back All-Star seasons as the Pirates’ closer, none of the players the Sox have added enjoyed a banner season in 2012.

Outfielder Shane Victorino, 32, was dumped at midseason by the Phillies. Pitcher Ryan Dempster, 36 on May 3, was traded by the Cubs to the Rangers, who were hoping for a booster shot to their playoff hopes only to see Dempster dinged and dented by the American League and ultimately get KO’d in a winner-take-all Game 162. Stephen Drew, 30 on March 16, was recovering from a fearsome ankle injury, was traded by the Diamondbacks to the Athletics and actually posted a negative WAR (wins above replacement) for both teams.

Mike Napoli, 31, saw his batting average fall by nearly 100 percentage points with the Rangers, then failed his physical with the Red Sox because of a frightening hip condition. Koji Uehara, 38, was terrific when he was healthy, but he missed 66 games with the Rangers with a shoulder strain. Jonny Gomes, 32, and David Ross, 36, were fine role players, but Gomes started in 74 games, less than half a season, while Ross started 47.

This is how you affect a renaissance for a team that lost 93 games last season and alienated its fan base? Well, yes, according to the Red Sox, who believe they have assembled a veteran, experienced supporting cast to surround their core stars of Dustin Pedroia, David Ortiz and Jacoby Ellsbury, and a potential star in the making in Will Middlebrooks.

All of the newcomers come with question marks attached, none more so than Napoli, whose doctor insisted to the Providence Journal that Napoli's hip condition was caught in time to prevent rapid deterioration, though the Red Sox were sufficiently doubtful that they trimmed their offer to the first baseman-catcher from three years, $39 million to a one-year, $5 million base plus incentives.

But they also come with winning pedigrees and burnished reputations as positive clubhouse assets, attractive qualities for a team sorely needing an infusion of character after a September collapse in 2011 morphed into a season-long nightmare in 2012. All those positive vibes will mean little, of course, if Victorino doesn’t recapture the skills that made him so vital to the Phillies’ championship runs, or Napoli and Gomes fail to take advantage of a ballpark whose dimensions are tailor-made for their swings, or Drew doesn’t revive the promise he showed pre-ankle fracture, or Dempster doesn’t make a successful adjustment to the AL.

It’s also necessary to take something of a long view here. The Sox payroll will be in the $151 million area this season, but their guaranteed obligations drop off dramatically to $87.9 million in 2014, $29.75 million in 2015 and just $245,000 in 2016. The Dodgers will be paying $43 million just to Crawford and Gonzalez in 2015 and ’16, and years beyond. The opportunity remains for Cherington to remake the Sox in his own image in coming years; 2013 might be a year to regain respectability at the least, and be a dark-horse contender at best.

NEXT UP: Star power: fact or fiction?