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Lester might find pitcher-friendly NL enticing

MLB.com @philgrogers

Greg Maddux had five cracks at free agency, the first when he was 26, the last at age 40. He used that leverage to change teams three times, but he never changed leagues.

The Yankees and other American League teams tried to persuade Maddux to leave the National League, but they never succeeded. Maddux knew a good thing when he saw it.

Greg Maddux had five cracks at free agency, the first when he was 26, the last at age 40. He used that leverage to change teams three times, but he never changed leagues.

The Yankees and other American League teams tried to persuade Maddux to leave the National League, but they never succeeded. Maddux knew a good thing when he saw it.

"Do I look like an idiot?" Maddux said at the end of his career.

Just as bull riders are pulled to the west or valedictorians are drawn to Ivy League schools, veteran pitchers gravitate toward the NL, the last refuge from the designated-hitter rule. Earned run averages are lower, life expectancy seemingly longer.

That's worth considering, as the three top free-agent pitchers this offseason have worked 95 percent of their 4,745 2/3 innings in the AL.

Max Scherzer started his career with Arizona before being traded to Detroit. But Jon Lester and James Shields have only known life with the lowest margin of error for a pitcher, as they were drafted by AL teams and have never left the league.

If history is an indication, at least two of the three will wind up moving to an NL club. That's what pitchers do.

Consider this: There have been 13 pitchers with contracts worth at least $100 million; nine of those deals were struck with NL clubs.

When you eliminate the contract extensions that bound Clayton Kershaw, Justin Verlander, Felix Hernandez, Cole Hamels and Matt Cain to their clubs, you've got eight free-agent pitchers being rewarded with nine-figure contracts. Six of those eight opted for NL teams, including five who migrated to the NL after spending most of their careers facing DHs, those being Kevin Brown, Cliff Lee, Barry Zito, Johan Santana and Zack Greinke.

Free agency isn't a one-size-fits-all proposition, of course. Players are motivated by different factors. But the deck is stacked against an AL team competing with NL teams for pitching talent.

That's worth keeping in mind as the Red Sox work to get Lester to return to Boston only five months after they made him pack his bags for Oakland. At least five other teams have reached out to Lester's agents, Seth and Sam Levinson, including four from the NL.

You'd be foolish if you didn't think Lester ever talked to former teammate Jake Peavy about the advantages of pitching in the NL. He surely noticed how the 33-year-old Peavy went 6-4 with a 2.17 ERA for the Giants down the stretch this year after starting 1-9 with a 4.72 ERA for the Red Sox. That followed his career arc, as Peavy's ERA is nine-tenths of a run lower in the NL than the AL.

Given that Lester's next contract is expected to run at least six years, with a value that could extend beyond $150 million, you wonder if he'll be influenced by the chance to face the NL lineups that last year produced a .694 OPS with an OPS+ of 94 rather than the AL's .706/99. That doesn't seem like a huge difference, but pitchers know that a lot of times their success depends on who they are facing as much as how well they're pitching.

Here's a ranking of the Lester market:

1. Red Sox: While the concept gets thrown around every July, free agents rarely return to the teams that traded them. It goes against human nature to forgive and forget that quickly, and isn't the grass almost always greener in someone else's pasture? That said, this is a team that can use its sentimental, emotional pull and huge resources to get what it wants. The Red Sox have made it very clear they want Lester back to fill one of two holes at the front of the rotation. Boston probably shouldn't be favored, but the word around baseball is that it's a strong possibility.

2. Cubs: Lester knows firsthand how the Theo Epstein/Jed Hoyer/Jason McLeod front office works, and he developed a huge respect for new manager Joe Maddon while competing against his teams throughout his nine-year career (Lester's 4.08 ERA vs. Tampa Bay is his highest among AL East opponents). He's become a huge priority for the Cubs, who have been frustrated by making unsuccessful bids for Masahiro Tanaka, Anibal Sanchez and Hyun-Jin Ryu the past two years. Even though the Cubs haven't won more than 75 games since 2010, Maddon has said his goal is to compete immediately, and signing Lester would be a huge step forward. The Cubs have hoarded their payroll flexibility so they can win this kind of bidding war, and there are rumors that they could also sign Lester's favorite catcher, David Ross.

3. Giants: With Pablo Sandoval in Boston, committing to sign Lester would be the perfect bookend move to the $167 million extension that keeps Buster Posey under control through 2022. It's possible because in 2012, general manager Brian Sabean signed Madison Bumgarner to a five-year, $35 million contract that includes $12 million options for 2018 and '19. If there's a fear here, it's that Bumgarner would feel taken advantage of with an imported pitcher earning twice as much as him. But San Francisco is a very attractive spot for a free agent.

4. Braves: Having traded for Shelby Miller earlier this month, the signing of Lester would be a huge coup for John Hart, who recently replaced Frank Wren as the Braves' top baseball man. It would also give Lester the much-envied possibility of being a 12-month-a-year resident of one city, as he recently moved his wife and two children into a home near Peachtree City, about 45 minutes away from the site of the Cobb County ballpark due to open in 2017. The downside is that the Braves' lineup is in flux and they don't have a wave of young hitters coming, as do the Cubs.

5. Cardinals: Lester will reportedly visit St. Louis next week, and he'll almost certainly leave town with a great impression of the organization. That's what happens when anybody is introduced to owner Bill DeWitt Jr. and takes a hard look at how he has built a baseball haven in the Midwest, complete with that great Ballpark Village beyond the left-field fence at Busch Stadium. The Cards can offer the chance to throw to Yadier Molina and work alongside the highly respected Adam Wainwright. It's unclear if Lester is a priority or a whim here, however.

6. Blue Jays: GM Alex Anthopoulos and the Toronto ownership are dead serious about building a team that can have a long run atop the AL East. They have a nice mix of impact veterans and talented young players, and added a big piece by signing catcher Russell Martin to a five-year, $82 million deal two weeks ago. But Martin was coming home to Canada, and many Major Leaguers are reluctant to cross the border. This is a tough sell, but Toronto could make the highest offer.

7. Mystery team/Yankees: GM Brian Cashman has played things close to the vest this offseason, as he always does, but it would be foolish to rule out the Yanks in regard to any of the top free-agent pitchers. They have needs and the history of giving their fans the best team possible. The Dodgers are probably the next more likely team to step into the process late, even if they already have Kershaw and Greinke. The Rangers could use Lester, but they don't seem to have left themselves flexibility to add him after bulking up on Prince Fielder and Shin-Soo Choo last year.

Phil Rogers is a columnist for MLB.com.

Jon Lester