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What is the most team-friendly extension in baseball?

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Who gave their club the biggest hometown discount?

Jim Rogash

The Red Sox are discussing an extension with pitcher Jon Lester and it seems that Lester and his agents are agreeable to a team-friendly contract. I can’t help but smile in wonder at the trend of team’s extending players before free agency. It is a simple idea, really. If you have exclusive negotiating rights for a time, you should use them and try to get a good deal before bidding war can possibly breakout.

If you are player and you are making millions of dollars anyway, isn't it worth something to stay where you have built your reputation and won over the love of the fans? Baseball’s long development process and the unique process that players pass through in their way to free agency also helps to make extensions extremely appealing for both sides.

But I have to smile because in some ways, this trend is a complete rejection of the tired and worn cliché that free agency is ruining the game. In the days of the reserve clause, there was basically zero loyalty between players and owners. Players had no choice but to keep playing for the same team or else leave the game of baseball entirely. In the early days of free agency, the bitter taste of that raw deal kept players and owners battling viciously and it would have been hard to imagine players just routinely taking less than the highest possible offer.

Now, a player like Jon Lester, who is just one season from an enormous payday, is willing to go without even testing the market and sign with the club that brought up through the majors and this is hardly even noteworthy. Free agency hasn’t destroyed player loyalty, it has created it. The very possibility that a player might knock off a few million dollars for the hometown team, or that a team might pay a player even a dollar more than they are contractually obligated to is entirely the product of baseball’s semi-free market.

The Red Sox are no strangers to the home team discount. Star second baseman Dustin Pedroia signed an eight-year, $110 million contract with Boston two years before he would have become a free agent and gotten to compare his numbers to those of Robinson Cano and his $240 million deal.

Pedey’s deal is a good candidate for the most team-friendly extension in the game today, but it isn’t the only candidate. Even the gigantic deal that Clayton Kershaw got from the Dodgers might have a little home town discount in there somewhere. You’ve got Evan Longoria, David Wright, and many other worth candidates to consider.

So who has the most team-friendly deal in the game?

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