There were a couple of big baseball stories around the end of the All-Star break, but perhaps the biggest news was reported by Yahoo! Sports last Friday, that the Boston Red Sox had placed a contract offer on the table for All-Star second baseman Dustin Pedroia, extending his deal by five or six years for $100 million or more, with the average annual value of the extension somewhere around $20 million.

Outside of the contract then-shortstop Alex Rodriguez received from Texas in 2000 -- a 10-year, $252-million deal that the Rangers later traded to the New York Yankees -- the extension would make Pedroia the highest paid middle infielder per year in league history and probably keep him in Boston for the remainder of his career. Pedroia will make $10 million next season under his current deal, which also includes a team option for 2015, at $11 million, that presumably would be replaced by the new extension.

Which brings us to the literal $100 million question: Is Pedroia worth locking up for that long, and for that much? If the offer is really on the table (while all parties involved have declined to comment, there haven't been any denials), then we already know what the Boston front office's answer is. But assuming the extension is signed, there's a lot to worry about Pedroia's game that could turn this into a nightmare contract, by the time everything is said and done.

A lot has been written this year about the viability of second basemen as they age into the back end of their careers, and what that should mean for second basemen signing contracts that will take them into their mid to late 30's. The vast majority of these pieces have been focused on Yankees second baseman Robinson Cano, who will be headlining this year's free agent class and seems destined to get some sort of 10-year, $225-million-or-more monstrosity of a deal from either the Yankees or the Los Angeles Dodgers. But the general takeaways apply to Pedroia too.

Second basemen play the highest-stress position in the game outside of catcher, and as a general rule, they see swift and harsh decline in both their ability to play and their ability to stay healthy as they move through their early 30's due to that stress. Pedroia's biggest issue moving forward is probably going to be that second one; for all the plaudits he gets for playing the game gritty and tough and hard and right, he's also landed on the disabled list three times in the past four seasons and been dinged up much more than that, playing through injuries that might sideline other players. He's currently playing through a torn ligament in his thumb, for example, that usually takes a month or two to heal, and if the injury worsens due to his breakneck style, it could require surgery.

Boston sportswriters and fans love that sort of hockey-player mentality from him -- see this article about it from the Boston Herald, titled "Dustin Pedroia toughs it out despite injured thumb" and subtitled "Sox' heart and soul won't be kept down" -- but that stubborn unwillingness to leave the game, combined with the violence with which he plays his position, raises an already substantially high risk factor about his health. Orioles second baseman Brian Roberts played tough and stupid, too, and it cost him most of his early thirties.

Pedroia's career as a hitter is pretty much a creation of Fenway Park; he has a career OPS of 893 at home and 766 on the road, meaning that outside of his home field, he's basically Howie Kendrick, a decent player to whom no one is clamoring to give hundreds of millions of dollars. He's as much a product of Fenway as Carl Yastrzemski (904 OPS home, 779 away). That would be a giant red flag for any other team that might consider signing him, and hypothetically, it would -- or should -- should bring his price down a bit on the open market. But the Red Sox have to worry about that; the effect that playing in Boston has on his numbers clearly is sustainable, and Fenway Park isn't going anywhere anytime soon.

Additionally, there's no way to tell whether or not the market for Pedroia would develop in any rational way, considering that if the Dodgers don't get Cano, they probably would feel little compunction about throwing that same kind of money at Pedroia, were he to test the market in 2015. For at least the next couple of years, the monsters of Chavez Ravine should be quite effective bogeymen for agents to use in negotiating extensions, scaring teams into committing more years and dollars than they might otherwise, lest the Dodgers swoop in and give their player a deal the size of the GDP of Texas.

The current Red Sox regime, from ownership down through the front office, are also obsessive culture warriors; like their counterparts in the Bronx, they have a very rigid idea of the Boston Red Sox brand, and they're willing to excise talented players who don't match that brand and overpay veteran players who enhance it. The startling turnaround the Sox have had between 2012 and 2013 won't make that any less true, even though some of the offseason's bigger acquisitions -- Shane Victorino, Jonny Gomes, Mike Napoli and Ryan Dempster -- have ranged from merely acceptable to disappointing.

Pedroia is the rare combination of a player who can perform at a very high level on the field and who embodies the message, look and narrative that the Red Sox want their brand to communicate. Just like the contracts Derek Jeter has been getting in his twilight years, the Red Sox brass will be willing to overpay to keep that, because overpaying to strengthen the brand is, in and of itself, a message that strengthens the brand. You'll see this mostly couched in talk about Pedroia's "leadership" and "locker room presence" (which has been ridiculued by everyone from bloggers to David Ortiz himself, in an unguarded, frustrated moment), but there's just as many real-world, positive implications for the Sox off the field with Pedroia as a life-long Red Sox as there are on it. The Sox just have to remember not to sign too many of these deals, and hope they work out well on the back end -- or brand consciousness won't be the only thing they'll be sharing with the recent Yankees squads in a couple years.