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Roche: Exploring Pros, Cons Each Team Presents To Jon Lester

BOSTON (CBS) -- As we wait for Jon Lester to finish up his free agency tour, let's take a look at some of the pros and cons of the places he may end up:

Atlanta Braves

Pros: Much has been made of the fact that Lester currently resides about 30 minutes out of Atlanta, and I get that it could play a factor. Lester likes being a creature of habit. He likes a comfort zone. And why not? Lester can be close to his family year-round.

However, I still think Lester likes going "home" - if you will - after each season. I think he likes his routine of Fort Myers-Boston-Georgia on a yearly basis. But, yes, I'm sure living and playing in Atlanta could be a factor.

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Cons: The Braves just traded away Jason Heyward and have reportedly been dangling Justin Upton in trade talks. One has to wonder if they're rebuilding for their new ballpark down the road. Why would Lester want that when he's in his prime right now? And, would it make sense for the Braves to dish out top dollar right now for a starting pitcher? I just don't think the timing is right.

Odds: 5-1

Chicago Cubs

Pros: Theo Epstein and Jed Hoyer. Lester grew up with them in the Red Sox organization and won two World Series titles with them in Boston. There's a trust and belief in how they do things. I'm sure Theo laid out his exact plan for the Cubs and how Lester fits in; Joe Maddon is now in place, and it appears that Lester is next on Theo's list. Those two would be great for all Chicago's up-and-coming kids.

Theo could also sell the "let's end another curse" motto too. And, Cubs fans don't carry the hard edge that Boston fans do.

Cons: Much like Atlanta, how close are the Cubs to winning a World Series title? They have really struggled since Epstein took over and seem to have a ways to go -- although having Maddon certainly helps.

Odds: 5-1

St. Louis Cardinals

Lester St. Louis
Lester walks off the mound at Busch Stadium following Game 5 of the 2013 World Series. (Photo by Rob Carr/Getty Images)

Pros: This looks like a potential great fit for Lester. St. Louis has a great fan base, a great ballpark, and is a wonderful city to play for. There's also a team in place that can win now with a good mix of veterans and youth: Matt Holliday, Jason Heyward (great addition), Matt Carpenter, Jhonny Peralta, Colton Wong,  and Matt Adams. Plus, the great Yadier Molina is behind the plate, and they have plenty of veteran pitchers who Lester would enjoy pitching and hanging with in Adam Wainwright, Lance Lynn, Jamie Garcia, Michael Wacha and of course, John Lackey -- a guy he was tight with in Boston. The Cards also have a former catcher as a manager in Mike Matheny, so there is a lot to like for a pitcher.

Cons: Can -- and do they -- want to pay Lester what it will take to sign him? Wainwright will make $19 million in 2015, so do they want to add another $20 million plus salary? They have Holliday at $17 million, and Molina and Peralta will each earn $15 million next season (though Holliday and Peralta come off the books in a year or two).

Odds: 5-2

Kansas City Royals

Lester KC
If he ends up with the Royals, will Lester be pitching in front of packed houses each time he takes the mound? (Photo by Ed Zurga/Getty Images)

Pros: Much like the Cardinals, there's a lot to like about the Royals. Lester would take over for James Shields as the ace of their staff. And, there are a lot of good pitchers on the staff from Jeremy Guthrie to Jason Vargas to Yordano Ventura, and they have a great bullpen as well. You've also got a solid lineup that can play great defense, and Salvador Perez is an elite catcher.

Cons: Lester would take up one-fifth of the KC payroll, which may not be the best thing for a small/medium market team. Meanwhile, the Royals had a tremendous run to the World Series last season which energized the fan base, so 2015 should be fun with plenty of fans in the ballpark. But, if they have a down year in 2015, Lester could be stuck pitching in an empty ballpark. He has always said that he loved the intensity of Fenway, and fed off of it. Chances are he wouldn't get that in Kansas City.

Odds: 8-1

Toronto Blue Jays

Lester Toronto
Lester is 7-6 with a 3.47 ERA in 17 career starts in Toronto, striking out 109 batters over 111.2 innings. (Photo by Abelimages/Getty Images)

Pros: Lester would step in as the ace of a good team, followed by Marcus Stroman, R.A. Dickey, Mark Beuhrle and company. He also would have a great lineup led by Jose Bautista, Edwin Encarnacion and Jose Reyes. The Jays just added a solid veteran catcher in Russell Martin.

Cons: Would Lester enjoy pitching in a market where hockey is king and always will be? I can't picture Lester liking it there and he's a career 7-6 at Rogers Centre (his other numbers are OK though). It would really surprise me if he picked the Jays over everyone else.

Odds: 10-1

Boston Red Sox

Lester Fenway
Lester is congratulated by Red Sox teammates in the Boston dugout. (Photo by Jim Rogash/Getty Images)

Pros: There are lots of them. He has been successful here for a long time, enjoys the intensity and electricity in the ballpark and is very comfortable with his family in this city. The Red Sox will always spend money to contend.

On the field, he'll be throwing to Christian Vazquez and a veteran back-up. Lester loves Ben Cherington, John Farrell, Juan Nieves, David Ortiz, Dustin Pedroia, etc, and is very comfortable with clubhouse staff, family room, city, and the list goes on and on. I think all of this is very important to Lester. He knows what it takes to be the ace of this staff and embraces it.

The Sox defense should also be improved, especially if they get Pablo Sandoval to man the hot corner.

Cons: The Sox brass totally mismanaged negotiations last season. This should have and could have been an easy deal to get done last year in Spring Training. Can Lester put his faith and trust in getting a reasonable deal done? Do they really, really want him back?

What will it take to get a deal done? six years, $130-150 million? Will the Sox go that high? Will some other team go much higher?

Odds: 5-2

Summary

Most of these teams would be a great fit for Lester, and I actually think there are more that would be a great fits as well: The Angels, Mariners, Rangers, Orioles, Dodgers, and Yankees all fit. It wouldn't surprise me if one of these teams emerge as a mystery team when all is said and done. How good would Lester look in the Angels starting rotation with Jared Weaver, CJ Wilson, and Matt Shoemaker? Or how about with King Felix in Seattle (although they need offense)? Or atop the Yankees rotation?

I'll give each of those teams 6-1 odds to land Lester.

However, Boston is the team Lester should be with in 2015 and beyond, but you just never know. I'd love to see him back in a Red Sox uniform, but it wouldn't shock me if it's somewhere else.

Follow WBZ-TV's Dan Roche on Twitter @RochieWBZ.

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