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12/02/11 12:01 AM EST

Of new skippers, Bobby V has toughest task

And so, with perhaps the boldest move of all, the managerial landscape has been set.

The Red Sox announced the hiring of Bobby Valentine on Thursday, marking the end of a 60-day search for their new skipper and (barring a late change of direction) filling the final managerial vacancy in baseball.

The five teams that made a change at the helm for 2012 took on their own set of risks with their new skippers. Now these skippers will take on their own set of difficulties.

Dale Sveum will try to reverse a curse on Chicago's North Side.

Bobby Valentine
Bobby V hits Beantown

Robin Ventura will try to manage a roster in flux on the South Side in Chicago.

Bobby Valentine will try to fix a clubhouse in Boston.

Ozzie Guillen will try to energize a franchise in Miami.

And Mike Matheny will try to fill some awfully big shoes in St. Louis.

Here's how the difficulty of these new jobs ranks, starting with the toughest.

1. Valentine and the Red Sox
Roster strength and popularity make managing the Red Sox a dream job.

Recent history makes it far from that for Valentine.

It's not just that anything short of a World Series championship in Boston is now considered a disappointment, or that the man he's succeeding was loved by the players he now has to reach, or that he'll compete in baseball's toughest division, or even that this team totally underachieved by collapsing in unprecedented fashion just a few months ago.

It's that in Boston, Valentine somehow has to run a much tighter ship and hold players much more accountable than Terry Francona did -- even though he's the new guy, and even though he's taking over a veteran-laden team with plenty of egos.

Bobby V. needs to push such guys as Jon Lester, John Lackey and Josh Beckett (the three starters alleged to have gone on a fried-chicken-and-beer diet last season), ease the tension out of Carl Crawford (the expensive outfielder who may have been trying too hard through a disappointing 2011) and appeal to the core guys: Dustin Pedroia, Kevin Youkilis and (if he re-signs) David Ortiz.

Can Valentine -- smart, tactical, brash, unafraid and polarizing -- get the most out of a loaded roster that's ready to compete for titles on paper but may still be reeling mentally?

That's the big question that's still impossible to answer.

2. Matheny and the Cardinals
Forget managing. Matheny has never coached professionally. Now he'll be trying to fill the shoes of the Hall of Fame-bound Tony La Russa, will be taking over a team that just won a World Series and is going to manage in a baseball-crazed city with some of the most passionate fans in the country -- and he may have to do all that without Albert Pujols.

One thing Matheny has on his side -- and one thing that made him the man for the job, regardless of track record -- is personality. He can be tough, inspiring and lovable all at the same time, and that's tough to attain, even with a world of experience. The key players on the Cardinals -- from Chris Carpenter to Yadier Molina to even Pujols -- love Matheny and, most important, respect him.

But it's only natural that he'll commit some rookie mistakes as manager. How will his players react if some of his in-game decisions cost victories? How will the fan base treat him if things start going bad? And how will he deal with all the intricacies that come with being a professional manager -- dealing with the media, filling out a lineup card, managing a bullpen, juggling egos, benching players and being second-guessed?

Nobody knows, because nobody has seen Matheny do it.

Because of that, this is a risky hire. And because of that, this is a tough proposition, despite the recent success and the talented roster.

3. Sveum and the Cubs
Congratulations on finally landing that full-time managing gig, Dale Sveum. Here's your team. It hasn't won a World Series championship in 104 years (yes, that's right, 104 years) and is coming off a 91-loss season. One guy who's making $18 million (Carlos Zambrano) may not throw a single pitch for you in 2012, and one player owed $54 million over the next three years (Alfonso Soriano) isn't quite the same.

When can you start?

OK, so it isn't really that bad of a situation Sveum is inheriting with the Cubbies. In fact, there are a lot of things to like about the new gig.

• It's a big market in a great city with a loyal fan base.

• The new direction under president Theo Epstein seems quite promising.

• The expectations are pretty ideal. If Sveum doesn't deliver a title, he's merely the latest in a long line of lovable losers; if he does, he is nothing short of a folk hero.

But it won't be easy, even with Theo onboard and even if a big-name player such as Prince Fielder joins. Many have recently taken the helm in Chicago -- from Jim Riggleman to Don Baylor to Dusty Baker to Lou Piniella -- thinking they'd be the ones who finally reversed the curse, only to come up short.

Sveum will have to manage through a rebuilding effort, from the elimination of bad contracts to the makeover of a farm system to the addition of winning players.

The question is: Will he have a long enough leash to ride out that rebuilidng effort and cash in on the potential glory years?

4. Guillen and the Marlins
It's easy to be excited about the Marlins right now, with their new stadium, their new look and their newly aggressive approach to free agency.

But the honeymoon will soon end for Guillen, paving the way for plenty of questions.

Can he make this team a contender? If Jose Reyes signs, can he be the man to convince Hanley Ramirez to move to third base? Can he, with his unfiltered personality, get along with a front office that doesn't tend to favor outspokenness?

And, most important, can he sell baseball to South Florida?

That's the big question not just for Guillen but for this franchise as a whole. The Marlins have ranked at or near the bottom in attendance throughout their existence. Because of that -- and because they shared a stadium with the Miami Dolphins -- the Marlins didn't usually have the funds to sign the big-name players.

Now, apparently, they do.

Now their payroll is expected to jump from last year's $58 million to at least $85 million in 2012.

Now it'll be up to Guillen -- part manager, part marketer in his new role -- to use a better venue and a better roster to make the Marlins a team that not only wins consistently but draws consistently.

A tall order, indeed.

5. Ventura and the White Sox
All those questions that surround the inexperienced Matheny? Same goes for Ventura. Like Cardinals general manager John Mozeliak, White Sox GM Ken Williams took on the risk that comes with hiring a rookie manager because of what he showed as a player.

Now, like Matheny, Ventura will be doing plenty of on-the-job learning.

Unlike Matheny, though, Ventura doesn't have an ideal roster.

The White Sox front office went all in last offseason, ballooning the payroll to nearly $128 million, but only got 79 wins out of it. Now they have to pick a direction. Do they try to improve on a talented, expensive but underachieving roster, or do they blow up the whole thing and start all over?

That decision will ultimately fall on Williams.

The state of the franchise means the pressure won't be as high for Ventura. And considering that Ventura will get along with Williams a whole lot better than Guillen did -- it's hard not to -- he should be given plenty of rope. But it'll be up to Ventura to get the most out of whatever team he inherits to satisfy a traditionally fickle fan base.

He has a lot to learn. And he needs to learn it fast.

Alden Gonzalez is a reporter for MLB.com. Read his columns and his blog, listen to his podcast and follow him on Twitter. This story was not subject to the approval of Major League Baseball or its clubs.