Jon Lester Signing With Cubs Leaves Red Sox Searching For Alternatives

The Boston Red Sox don’t need to apologize.

Jon Lester carved out an impressive career with the Red Sox and served as a valuable member of the Boston community, but the organization must immediately turn the page rather than explain itself for losing to the Chicago Cubs in free agency. The Red Sox can’t afford to botch Plans B, C, D, etc., because they’re too busy worrying about where they went wrong with Plan A.

But what is the Red Sox’s next move now that they came up short in the Lester sweepstakes? Boston still has a ton of flexibility, both financially and talent-wise. It’s time for the Red Sox to start using their resources to build a formidable rotation for 2015.

Philadelphia Phillies ace Cole Hamels has long been considered a viable Plan B, in large part because his career track record is very similar to Lester’s and it’s clear they’re rebuilding in the City of Brotherly Love. But while acquiring Hamels would help fill the void created by Lester’s departure, it also would be a rather curious move, all things considered.

The biggest selling point with Hamels, who turns 31 later this month, is that his contract, on the surface, looks team-friendly when stacked up against the deals being signed by pitchers on the open market these days. Hamels is owed $90 million over the next four seasons, though it’s possible the lefty would require that Boston pick up his $20 million option for 2019 in exchange for waiving his no-trade clause.

All things being equal, a five-year, $110 million commitment looks more palatable than the six-year, $155 million contract Lester reportedly received from the Cubs. But all things aren’t equal.

Since Hamels’ contract includes a $6 million buyout for 2019, his salary for each of the next four seasons counts as $24 million, for luxury tax purposes. That’s less than Lester’s $25.83 average annual value with the Cubs — though not by much — and actually more than the average annual value ($22 million) of Boston’s reported six-year, $135 million final offer to Lester. In other words, Hamels really doesn’t represent a discount until 2019, at which point his salary would count as $14 million, for luxury tax purposes.

The biggest inequity in landing Hamels rather than Lester, however, is the obvious. Signing Lester in free agency was all about dollars and cents, whereas the Red Sox would need to relinquish talent — in addition to spending dollars and cents — to acquire Hamels. And judging by Phillies manager Ryne Sandberg’s comments Tuesday at the Major League Baseball winter meetings in San Diego, the organization still is shooting for the moon as far as what it expects in return.

“There’s no way that (Phillies general manager Ruben Amaro Jr. is) going to just give away a player,” Sandberg told reporters. “I mean, we’d have to be wowed to give up a guy like Cole Hamels, which would be a ‘wow’ that would help us with the process and go in the direction that we want to go.”

There’s been conflicting reports as to whether the Phillies would require that the Red Sox include Mookie Betts, Blake Swihart, Xander Bogaerts or Henry Owens as part of any trade for Hamels. Boston undoubtedly would have to relinquish prospects it doesn’t necessarily want to relinquish, though, which is rather unsettling in an era when young, cost-controlled talent is as vital as ever.

Thus, Hamels doesn’t represent an ideal Plan B, as some have suggested. Rather, the Red Sox are better off pursuing another free agent, like James Shields, and coupling him with a pitcher who would require less of a commitment, both from a trade compensation and a financial standpoint.

The Cincinnati Reds have four starters slated to become free agents next season — Johnny Cueto, Mat Latos, Mike Leake, Alfredo Simon — and it sounds like they’re willing to talk trades, though it certainly would be difficult to pry away Cueto, who is an underrated ace.

The San Diego Padres have a trio of pitchers — Tyson Ross, Andrew Cashner, Ian Kennedy — who they’re reportedly shopping around.

The Washington Nationals are worth calling to see what it would take to obtain Jordan Zimmermann or Doug Fister.

If the Red Sox can leverage their assets — most notably their outfield depth and their surplus of young pitching — to acquire a proven starting pitcher or two, losing out on Lester will sting a bit less.

It isn’t time for apologies. It’s time to roll up the sleeves.

Thumbnail photo via Steve Mitchell/USA TODAY Sports Images