It was Spring Training of 2014 when it was announced that the Red Sox had made what was then considered a “low-ball” offer to Jon Lester of 4 years / $70 million.

One of the reasons for the low offer at the time was that owner John Henry didn’t believe that pitchers who were over the age of 30 deserved to long-term contracts of over four years or more.

So after rejecting the offer the Red Sox traded Jon Lester to the Oakland Athletics in July in hopes they could convince him to re-sign with them to an appropriate deal during the offseason.

The Red Sox made an offer to Lester during that year’s Winter Meetings for about 6 years / $110-120 million, which seemed like a much more appealing offer.

However, when it was announced that Lester would be accepting the Cubs offer of 6 years for $155 Million (with an option for a seventh at $25 million) it completely once again made the Red Sox offer look small.

Of course, it had to be former Red Sox GM, Theo Epstein that swayed the beloved ace to Chicago.

Lester has a 46 – 28 record with a 3.26 ERA in his time with the Cubs, appearing in 107 games, as well as pitching in 11 postseason games over the past two seasons.

What were the aftershocks in Boston?

In 2015, after losing out on Lester, the Sox traded for Rick Porcello and Wade Miley and signed Justin Masterson to round out a rotation that was led by Clay Buchholz (woof).

After the 2015 season, which was a disaster, it led Dave Dombrowski to go out and sign David Price that winter to a 7 year / $217 million deal.

That was not merely enough as Dombrowski struck again to land Chris Sale just last season.

Now Sale is far and away one of the best pitchers in baseball, but the Red Sox were forced to part with two of the best young talents in Major League Baseball: Yoan Moncada and Michael Kopech.

With Price, the jury is still out on whether or not he will live up to his contract. In his first season, he had modest numbers, striking out 228 and pitching to an unusually high 3.99 ERA.

It was his post-season debut that he failed to deliver in – getting walloped by Cleveland who went on to sweep the Red Sox in three games.

Last season, Price began on the DL and pitched adequately for two months, but was once again relegated to the DL until September. Upon his return, he was shifted from the rotation to the bullpen and was dominant for the rest of the season and into the playoffs.

Heading into 2017, Price is healthy and is expected to join Porcello, Pomeranz, and Sale as the leaders of the rotation under new manager Alex Cora and pitching coach Dana LeVangie.

Though, the Sox on paper looks to have a decent if not great rotation, I’m left to wonder what could have been if the Red Sox had been able to sign Lester to that Six-year deal?

Would Cherington have acquired Porcello and Miley? Would Price have agreed to have come to Boston? Would Dombrowski have had to have traded for Sale?

One can only wonder, but the Red Sox certainly miss Jon Lester.