All five left the Red Sox - for various reasons - and eventually won a World Series with the Yankees.
It's not too much of a leap these days to see Jon Lester pitching for the Yankees next season and perhaps someday soon joining that list.
We had a little fun with Photoshop to offer a real-life look at what Lester may look like in Yankee pinstripes.
Not too pretty, is it?
Pictures are worth at least 1,000 words or one good Instagram post. Visualizing Lester as a Yankee is a lot more disturbing once you can actually see it.
OK, we'll make it stop.
But only the Red Sox and Lester's agents can make it stop in real life.
It's scary how the predictable the scenario goes that sees Lester end up wearing Yankees pinstripes. Red Sox open negotiations with ridiculous low-ball offer. Talks sputter on and off during the season. Fans and media types are barraged with slogans like "Over 30 Means Over the Hill," "Five-Year Contracts Must Be Stopped," and "Value is Good."
The Red Sox fail to make the postseason. The focus on Lester's fate sharpens. Larry Lucchino preaches calm. Lester becomes a free agent.
Eight seconds into free-agency, Lester signs a six-year, $148-million deal with the Yankees.
Red Sox fans will then be subject to in-depth reports breaking down the numbers behind failed free agent pitchers. We'll hear how Lester's agents looked at Ben Cherington sideways. We'll be reminded - again - of Lester's role in the "Chicken and Beer" scandal. By Christmas, Lester will be the most vilified former member of the Red Sox this side of Carl Crawford and Josh Beckett.
Whatever usable arms the Red Sox sign via free agency or manage to acquire via trade will be lauded as "statistical steals." Those of us idiots who know a rotation with Lester will be far more effective as a rotation without Lester will be mocked as uninformed traditionalists who cannot understand the intricacies of the post-Moneyball era.
That's the plan, anyway. But Red Sox fans won't be buying this time. The over-40 crowd (the ones who still buy most of the season tickets and tune in on NESN) will remember the sting of losing Carlton Fisk because the Red Sox front office screwed up and mailed his option-year contract offers two days too late. The way Lester's negotiations were handled on the front end were equally incompetent (Fred Lynn's option deal was voided at the same time as Fisk's, but the Red Sox eventually dealt him to California.)
The fans under 40 will have their own new special memories of how the Red Sox let their best pitcher since Curt Schilling ended up making 55,000 fans at Yankee Stadium cheer with delirium when he beats the Red Sox. Lester has averaged a 16-9 record with a 3.65 ERA over 162 games in his career.
Based on the current timetable, Lester will sign with the Yankees in time to wreck Thanksgiving. And come Christmas at Fenway, those brand-new 2015 ticket prices will be unchanged from this season, if we're lucky.
Line up here for your picture with Wally:
Zakim Bridge. Hello again Boston. Missed you. pic.twitter.com/RCMYhbbQye— Vertical Horizon (@VerticalHorizon) June 21, 2014
Think about that compensatory pick before you jump. Then you can jump.
Fisk ended up signing with the White Sox as a free agent and would play more games with Chicago than he did in Boston. He eventually went into the Hall of Fame as a member of the Red Sox.
Boston fans can always use that as a fallback if Lester manages to last long enough to compile Hall of Fame numbers in the regular season. He's already a Hall of Famer as far as the postseason is concerned.
Again, my favorite Lester stat is that he remains one of two Red Sox pitchers with an ERA below 1.00 in World Series play (minimum three starts).
The other is Ruth.
When it comes to big-game situations, Lester's loss would be Ruthian in scope to the Red Sox. The Babe was 3-0 in his three World Series games with the Red Sox, posting an 0.87 ERA in 31 innings. There were no ALCS or ALDS games this time last century. In the 2007 and 2013 postseasons, the two that ended with World Series titles, Lester is 6-1 with a bat-crushing 1.63 ERA in 44 innings.
All that, plus the fact that he's been with the Red Sox organization longer than any other player (he was drafted in 2002, six months before David Ortiz was signed as a free agent), carries a great personal story, and, reportedly, wants to stay in Boston.
We all know the "ifs" here are potentially historic in an Old Testament (i.e. pre-2004) Red Sox Level. Who knew that $70 million over four years would have been such an insult? Just about any Red Sox fan over the age of 14. And you have to look back no further than this past spring to see where the Red Sox violated their own "in-house" rules about contracts when Ortiz got his second annual Lifetime Achievement Award.
Jacoby Ellsbury's departure to New York was cushioned by the World Series hangover and the belief - at the time, anyway - that Jackie Bradley Jr. would be a capable replacement over the long term. There will no such goodwill this year. Nor will the Red Sox be able to replace Lester with anyone who has enjoyed similar pitching success in the postseason, unless Ruth plans on making a comeback.
In that sense, Lester is indeed one of kind.
At least in this century.
The OBF column is written by award-winning journalist and Bay State native Bill Speros. Hit him up on his Obnoxious Boston Fan Facebook page, on Twitter @realOBF or at his
Obnoxious Boston Fan Email Address. Thanks always for reading.
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