A pair of choice charter franchises bursting both with rich legendry and heavy baggage, the Cubs and Red Sox have meaningfully crossed paths only once. That would be in their 1918 World Series matchup that has been pounded into the consciousness of every New England school kid for generations on high, as if it ranked alongside Paul Revere’s ride on the scale of the region’s proudest moments whereas it actually yielded about as much to be proud of as the fate of Hester Prynne.

When they met in that September 96 years ago – the Series having been moved up a month to get the bloody season over with ASAP – both teams were being scorned as safe harbors for “slackers.”  World War I was ending amidst universal pain and disillusion; the shock of the war’s terrible cost was making a mockery of the premise that it had been waged as “the war to end all wars.” There was little taste for amusement, even that which baseball affords, not even in Chicago or Boston. Calls for the cancellation of the Series were widespread.

It was an argument that raged all the way to the White House before the green light was begrudgingly given – but only on the condition that the Series be swiftly and quietly played with as little cost and fanfare as possible, and with most profits going to such war charities as European refugee relief. As if their humiliation in having been virtually branded cads and cowards were insufficient, the players saw their Series shares cut to the bone.

So in the end, the familiar argument that baseball’s service as a morale booster always outweighs its seeming frivolity in times of crisis won the day. But the cost was high, resulting in the dullest and least joyful fall classic ever staged before the sparsest crowds and for the slimmest gate receipts.

Feeling that they’d been set up to play the goat role in the travesty, the resentment of the players boiled over. They tried striking before the last game, but succeeded only in making bigger fools of themselves. For years thereafter the rumor would persist that key Cubs had conspired to bag the Series mainly to get even. That the winning runs in the Red Sox last two decisive victories were the result of notably clumsy Cubs’ defensive blunders remains for many proof enough that the thing was probably “fixed,” or “dumped,” if you prefer. In short, the 1918 World Series was a total mess.

All of which makes the place and stature of that chapter in the lusty annals of Red Sox myth all the more perplexing, even amusing. Long lost in memory and dismissed in the popular culture is the irrefutable fact that 1918 was, by and large, a disgrace best forgotten. After all, it was the Red Sox players who were mainly responsible for the ill-advised and ultimately ludicrous effort to strike, which naturally played like a lead balloon at the height of the national war effort. 1918 deserves only a lasting place in infamy.

Instead, it has became a curious landmark, celebrated as the end of a glorious Red Sox run of championships and the high-water mark of Babe Ruth’s not long enough but no less illustrious service to the cause. It also became the war cry of the team’s rise from the ashes, culminating in 2004 with the reverse of the alleged “curse of the Bambino,” not entirely invented by Dan Shaughnessy, although he holds the copyright.

Meanwhile, in Chicago, diehard legions of the Cubs remain fixated on 1908, the last year they won anything. In the 106-year interval since then they’ve endured and survived their own bevy of prized and privileged curses, the most prominent of which has something to do with an aggrieved billy goat. From such odd circumstance does so much happy hoopla derive, albeit only in baseball.

Clearly, the Red Sox and Cubs must meet again at the pinnacle and only thereby will a final resolution of all this nonsense be possible. Does the Jon Lester caper, highlight of the recent and rambunctious baseball winter meetings in San Diego, advance that possibility? Ah, now, that is the question, eh. For sure, it’s their most interesting interaction since 1918.

Although they’ve both been around since horse and buggy days the Red Sox and the Cubs have done precious little business over the years. Among their minor dealings was Boston’s 1960 purchase of Bobby Thomson from the Cubs, with the Red Sox figuring the dead pull-hitter who had miraculously delivered the Giants over the Dodgers in 1951 was sure to fall in love with the leftfield wall. It was the height of that odd era in Red Sox history when they were devoted to the collecting of every large, aged, lead-footed, right-handed slugger they could get their silly mitts on. Sure enough, the Flying Scot soon proved well over the hill and was gone in three months.

In the winter of 1986, they sent Calvin Schiraldi to Chicago for the reliever Lee Smith. It amounted to banishment for Schiraldi, whom they blamed, no doubt wrongly, for having blown the recent World Series to the Mets. Smith, thought to be a potential Hall of Famer by some (but not me), was ordinary here while Calvin soon faded away in Chicago. Of far greater import was the 1984 deal that saw the Red Sox give up on the charming but exasperating Dennis Eckersley in the deal that brought the ill-fated Billy Buckner to town. In Chicago, Eck remained Eck, but when he got passed on to Oakland three years later, he blossomed into a Hall of Famer in the sort of miracle that never happened in Boston in those years.

In this muddled history, the Lester caper stands out big-time. It’s not their first notable free-agent confrontation. In 1993, the Red Sox plucked away Andre Dawson, although if memory correctly serves, the Cubs were rather indifferent about it. Dawson was near the end of the trail although in Boston he did perform ably enough to cap a career that landed him in Cooperstown.   

Lester is a very different matter. At the peak of his career, with his major place in Red Sox history secure, heavily in demand, very much still qualified to be an indisputable cog in any team’s scheme, and now bearer of a $170 million price tag, Jon Lester, the consummate stylish lefty, becomes the ultimate bone of contention in the relationship of two near-ancient adversaries.  

It has been an odd business. Why did the Red Sox handle it as they did? Did they blow it? Was the motivation of Theo Epstein, ex-of the Red Sox and now of the Cubs, as much personal as professional? Is Lester, never a 20-game winner or Cy Young medalist, truly an ace at age 32? Does this frisky business declare war between the ever-ambitious Epstein and the ever- grasping Henry-Luchino axis? Or are the Red Sox secretly if cynically pleased with how it worked out, as some suggest. It’s a good old-fashioned baseball scenario filled with delicious intrigue.

Otherwise, the Red Sox come away from the winter meetings doubtless feeling good about the opening salvos of their latest effort at improbable restoration, even as those inclined to quibble find plenty of fodder.

Some see the Lester melodrama as a defeat, possibly serious. But any team that walks away from an upwards of $170 million commitment to a thirty-ish pitcher can never be construed a certain loser. On the other hand, how is handing the Pablo Sandoval –Hanley Ramirez act roughly $200 million even remotely consistent? It says here they are going to mightily regret that Ramirez deal. And they won’t have to wait five years. The pitching they picked up so far is not overwhelming. Mr. Porcello has a chance to be exceptional, but he is quite hittable.

What fires Boston’s winter holiday dreams is the fact that their neighbors haven’t much brightened their hopes. Free agency has staggered the Orioles. The Rays, having lost their resident genius, stagger more. Toronto has been pro-active but can’t win with that pitching. It remains unclear what the Yankees’ game plan might be, presuming they have one.

But it’s still early in the Hot Stove Season. Very early! Except, of course, if you are a Cub.