|Scherzer is out of Boston's price range (Freep)|
1. Sign James Shields
Signing "Big Game" James Shields will probably require a five-year, $100 million commitment, which is hardly ideal for a 33 year-old who's thrown more innings than anyone since 2007. Shields has benefited from pitching-friendly venues in Tampa Bay and Kansas City throughout his career, which obviously won't be the case if he has to pitch in front of the Green Monster. It's also concerning that his strikeout rate has declined drastically over the past two seasons, from nearly a batter per inning in 2012 to the league average in 2014, a sign that his decline could already be underway. On the plus side, he has loads of postseason experience, is incredibly durable, and has succeeded in the AL East. His contract would compare favorably to those already signed by Hanley Ramirez and Pablo Sandoval, which is to say it will be expensive on an annual basis but won't linger into the next decade.
2. Trade for Cole Hamels
Hamels has said he wouldn't okay a trade to Boston even though the Red Sox project to be a much stronger team than the Phillies next year (and several after that). Philadelphia would be stupid not to at least entertain some Sox trade proposals, as Boston is rife with prospects while the Phillies' farm system is barren. The Phils have no use for Hamels, as they will be a terrible team with or without him, and by the time they're good again he'll be well past his prime. Hamels would be a great get for Boston, as he has been nothing short of outstanding throughout his nine-year career, with a 3.27 ERA (125 ERA+), 1.14 WHIP, and 3.77 K/BB ratio while averaging 200 innings per season. Like Lester, he's a lefty, a three-time All-Star, and a proven postseason pitcher. He's 31 and has never pitched in the American League, but he represents the closest equivalent to Lester besides Lester himself.
3. Sign Max Scherzer
Scherzer, a Scott Boras client, is going to blow Lester's contract out of the water. The 2013 AL Cy Young winner is almost seven months younger than the new Cubs ace and has been much better over the past three seasons, worth 16.9 bWAR to Lester's 8.3. I've heard reports that his price tag could approach $200 million over seven years, but I'd be surprised if he exceeds the $180 million Justin Verlander got two winters ago. The Tigers seem serious about re-signing him based on their $144 million extension offer last spring, and will push hard for him if they don't think David Price will stay beyond this year. I don't see the Sox committing so much money to one player when they refused to go over $150 million for Lester. Pitchers are just too risky.