If the Red Sox hope to compete next year, their top priority needs to be signing Jon Lester. Max Scherzer is out there as well and is considered a better pitcher than Lester--the top free-agent pitching prize on the market. He presents a bigger risk, however, as he has yet to make the transition from power pitcher to finesse pitcher and he has not played in a market like Boston. Lester has made the transition and he's spent all but two months of his career in Boston. Even though he's a year older than Scherzer, he is worth a long term (six-year) deal in the $150m range. I would certainly not be upset if the Red Sox sign Scherzer to a long-term deal, but I think they would be wiser to turn to the guy they know and they've watched develop.
As it stands right now, the Red Sox need two pitchers at the top of the rotation. Lester, should they be smart and pony up the $$$ and the years for him, solves the #1 slot, but who is #2? A free agent? Trade? There are a lot of nice options on the trade market, but none of them, short of the pipe dream of trading for Chris Sale, are at the level of Lester. Hamels is close, but his numbers in limited time against the AL have been abysmal. He would also cost a big prospect haul (Don't trade Mookie!). Johnny Cueto and Mat Latos of the Reds have been mentioned, as have Andrew Cashner and Tyson Ross of the Padres. The Red Sox need reliable pitchers atop the rotation because Joe Kelly is a #3 at the very best and who knows what we'll get out of Clay Buchholz. Then, we have the assorted flotsam and jetsam that toed the rubber in August and September to fight for the #5 spot. Getting that #1, however is the first step.
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