Red Sox and Jon Lester’s agents have talked twice about an extension

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Earlier today, D.J. Short told you about the reported interest between the Red Sox and starter Jon Lester in signing a multi-year contract extension. “Just how interested?” you ask. Two conversations interested, according to Nick Cafardo of the Boston Globe.

That’s a great deal of interest. As D.J. wrote, the extension could be in the $100 million range over five years. Considering the six-year, $105 million deal Homer Bailey signed with the Reds recently, that seems about right. Aside from atypical struggles in 2012, Lester has been dependable for the Red Sox. He finished the 2013 season with a 3.75 ERA in 213 1/3 innings.

The deadline is 8 PM ET Monday for Shohei Ohtani situation to be resolved

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Last Thursday, we learned that the MLBPA was challenging the Nippon Professional Baseball posting system, delaying Japanese superstar Shohei Ohtani’s move to Major League Baseball. The latest collective bargaining agreement removed a lot of the incentive for players to come to the U.S. by capping pay. Ohtani, for example, can only receive a signing bonus between $300,000 and $3.53 million while his team — the Nippon Ham Fighters — would receive $20 million for posting him.

Jon Morosi reports that the deadline for this issue to be resolved is 8 PM ET on Monday evening. He notes that key NPB officials have worked through the night in Japan to try to reach a resolution. It is possible that even if no agreement is reached, the deadline could be pushed further back.

Ohtani, 23, has become a heralded hitter and pitcher in Japan. At the plate over his five-year career, he has compiled a .286/.358/.500 triple-slash line with 48 home runs and 166 RBI in 1,170 plate appearances. On the mound, he has a 2.52 ERA with a 624/200 K/BB ratio across 543 innings.