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How a retiring Mark Teixeira should inform the Red Sox' offseason plans

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Nearly eight years ago, Mark Teixeira changed the course of Red Sox history by going to New York. So what does that have to do with the offseason to come?

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Mark Teixeira is announcing his retirement from baseball today. You might think that has nothing to do with the Red Sox' offseason plans, unless of course you're the one person out there who was really hoping he'd be David Ortiz' replacement. And you'd be right, unless of course you're willing to get tangential to relate current events with ideas you've wanted to talk about for a bit in which case welcome to the strangely specific club.

Teixeira's history with the Red Sox starts all the way back in 1998, when the Sox drafted him in the late rounds but, as expected, failed to lure him away from college. But for most Sox fans, first major contact came in the 2008 offseason, when the Red Sox were pegged as the favorites to land Teixeira in free agency right up until the Yankees swooped in and snapped him up as part of their huge half-billion dollar offseason.

At the time, it was quite the blow to the Red Sox, and left the Yankees on top of the East once more. And indeed, the Yankees would go on to win the World Series that year before starting a gradual decline to what seems likely to be a low point in 2016.

Once again, the Red Sox seem to be in the market for a big bat, this time to effectively replace the retiring David Ortiz. Whether their targets end up getting swept up by rivals or not, though, the Red Sox should strongly consider instead following the backup plan pursued by Theo Epstein once he missed out on Teixeira: signing the players they already had to extensions.

2008 had received three huge seasons from three Red Sox still under team control. Dustin Pedroia had earned American League MVP honors, Jon Lester emerged as the team's best young arm in the season that saw his no-hitter against the Royals, and Kevin Youkilis had a breakout year as his power emerged and he managed to maintain his success over the course of a full season for the first time. In the months leading into the season Epstein would guarantee the three just north of $110 million, locking in Pedroia through 2015, Lester through 2014, and Youkilis through 2013.

By now, you can probably see where I'm going with this: Betts, Bogaerts, and Bradley. Three of the game's best, all under team control, but none past the six years initially guaranteed to the Red Sox.

Photo Credit: Bob DeChiara

Looking at the likely roster for the 2016 Red Sox, there's actually not that many spaces to be filled. There's some work to do in the bullpen, sure. And of course David Ortiz' open spot. But this is not a team that demands re-invention unless some players perform very badly down the stretch. Even if the season does not end with the result the Red Sox hope for, there is reason to believe that the answer will not lie in big spending on free agents so much as running a similar group back.

The Red Sox will, however, have some money to spend assuming there's no great changes in budget incoming, thanks to David Ortiz ($16 million), Clay Buchholz ($13 million) and Koji Uehara ($9 million) coming off the books, in addition to a few smaller contracts.

Expecting none of that to go into free agency would be a bit naive, but still, the Sox should have plenty of room to make real offers to their young players in an attempt to lock them up long-term. No, it won't be as cheap as it was with Pedroia, Youkilis, and Lester. The fact that Scott Boras represents both Bradley and Bogaerts will certainly mean the Sox are going to have to open their wallets wide to get the job done.

Of the three, Bradley seems the hardest to actually work something out with. For one, he's got his mixed history working against him. But the real problem with Bradley is timing. As it stands, Bradley is set to hit free agency after the 2020 season, when he's 30 years old. That means that pretty much any extension with the Red Sox would mean he only hits free agency once his best years are past, leaving him unlikely to land another big contract. The Red Sox would love to have his age 31-33 seasons as well, but for Boras, agreeing to such a deal would go a long way towards diminishing the earning potential of the rest of his career. In this case, with four years still left to them, the Sox might just shrug and move on.

For Bogaerts and Betts, though, the story is different. Bogaerts is currently set to hit free agency after 2019. He will turn 27 that October. For Betts, it will be 28 in 2020. For both players, then, giving up their first three-or-so years of free agency would still leave them with the chance to land huge deals when they hit the open market, assuming they've continued to produce. It's an attractive combination of the security of an extension and the major earnings opportunity of free agency that even Scott Boras would have to consider if the Red Sox were willing to give Bogaerts reasonable value on those free agent years surrendered.

Obviously, at some point it does come down to brass tacks. Bogaerts has three years left, all of them in arbitration. Given how arbitration tends to work, he can probably expect to make some serious money over those years. Nearly two full season's worth of what he'd get in free agency. At the moment, it's anyone's guess what he might land in free agency, but as one of the game's best players, and far from the point where age should start to rear its ugly head, the answer is "a lot." Really, we should probably expect any Bogaerts extension to look a lot like a free agent contract, somewhere in the low nine figures for six-to-seven years.

But if that doesn't sound like the Red Sox are getting anything out of making the commitment early, they are. They're getting a shorter deal without Xander's age 34+ seasons, and importantly the ability to pay him 2016-2017 free agent prices for 2020 and beyond. If Bogaerts is a $23-25 million player right now, it's easy to imagine he's a $30+ million player a few years from now the way market prices have been trending.

The math is similar for Mookie Betts, though with one more year of pre-arbitration control and a non-Boras agent you can probably scale back a bit on that.

Looking back at the Teixeira saga, the Red Sox cannot be too terribly unhappy that they missed out on him. The Yankees will take their World Series win, yes, and he's ultimately given them a decent amount of value, even if these last years have largely been ugly. But can there be any doubt at this point that Boston's money was better spent? In the years Teixeira was actually a commodity for the Yankees (2009-2012), Youkilis outproduced him with a 131 OPS+ against Teixeira's 126. Dustin Pedroia is still one of the game's best second basemen. And while the words "Jon Lester" and "extension" tend to be more haunting to Red Sox fans these days than anything else, the one they did sign him to led to more than a thousand strong innings, and one year as the ace of a World Series winner.

So if the Red Sox choose to avoid the obvious high-priced bats of the offseason, that will be just fine so long as they put that money towards a different use. Extensions aren't flashy, and they don't actually improve the team over the previous iteration, but they're often the best move a team can make in the long term.