Red Sox: Looking back on Boston’s divorce from Jon Lester in 2014

Former Boston Red Sox lefty Jon Lester hints at a possible Boston return. He never should have left and the cost has been substantial for his departure.

In baseball certain items of mention become factual simply because they are repeated so often that they are taken as truth. One is that the Red Sox farm system does not produce valuable starting pitching and that truth is difficult to debunk. There is no conspiracy theory but there is evidence and it is no display with the projected rotation for 2020. I can spot a Red-flanked bluetail bird quicker than a competent homegrown arm.

This has caused bitter repercussions as the Boston payroll is top-heavy in paying for outside intruders to provide what the farm system should have produced. So much for the Captain Obvious negativity, but what frosts me over is not keeping a prize that has produced and then replacing with a more costly replacement.

The Red Sox let Jon Lester walk but the walk was preceded by trade to Oakland. Lester for Yoenis Cespedes who also was a pending free agent. Oakland – not known for tossing free agent monies to the wind – let Lester go to the market where he signed with the Chicago Cubs. A former Red Sox executive commander thought enough of the lefty to honor him with a six-year and $155 MM deal.

What were the Red Sox thinking? Once Lester was safely stuffed into the rotation there was a guarantee between 2008-13 of 30+ starts each season. When Lester was shipped to the A’s it didn’t change as Lester had a combined 32 starts for 2014. In the same time frame, Lester only had one season (2011) of under 200 innings pitched. Did the Cubs get their monies worth?

In his five seasons with the Cubs, Lester has made the usual 30+ starts, but his innings pitched have been modified downward. Lester has punched out a 74-41 slate and a 3.54 ERA with the Cubs and a World Series ring. Lester is the personification of a durable workhorse on the bump and has the rings to prove his value in crunch time.

Curt Schilling was a great pitcher who took it to another level in the postseason. Reputations can be made – positive or negative – in the playoff pressure cooker. Lester is 4-1 in the World Series (3-0 with Red Sox) on his go around and 9-7 in the second season when it is all on the line. Those last five seasons should have been in Boston and not Chicago. Instead, we got a replacement – David Price. No Mr. October there.

Price was a very good pitcher who became just a good pitcher with the Red Sox and occasionally a horrible one. The inconsistency of not being reliable being one point, but an expensive point is the costly concern is a contract that Boston will continue to pay. Return on investment has been a fiscal tragedy.

Price was gifted with seven years and $217 MM of which the Red Sox are now obligated to pay the Dodgers $16MM a year for the next three years for their willingness to take what we have grown tired of dealing with. Paying to get rid of a player speaks volumes. The Red Sox seem to have cornered the dead money market.

Irascible is one way to describe Price, but I have read for more creative terms on social media. Sometimes in marriage, a divorce is necessary and this one was long overdue. Price had conflagrations with fans on Twitter, innocent bystander reporters, broadcasters, and in all probability management from the corner office to the bench. I am sure the clubhouse was not a happy home for Price, either.

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The current Mookie Betts situation is somewhat valid in comparison to Lester being sent elsewhere. A proven Betts shipped out for question marks. Lester the valuable was likewise sent out elsewhere and replaced for a more costly item. Just how would that $16 MM currently be carted to L.A. look if removed from the Red Sox luxury tax situation? The Red Sox had the real deal – a proven winner, inning eater, competitor, and homegrown product. They screwed up.

I will give a devil his due moment when Price finally dumped his horrible postseason miseries in 2018.  Price’s 2-0, 1.98 World Series certainly did that  – it was Lester

If Price had been the real deal this all in hindsight would be unnecessary but the real issue is keeping a productive, proven, and valuable arm on the home fires. Lester never should have been a Cub. Lester was willing to make contractual adjustments but it failed. Now Lester has hinted at a return, but that may just be as likely as “Booby” Valentine returning to manage.

"“Absolutely it would be cool to go back and finish my career where it all started.” – Lester on a Boston return"

Lester is coming off a 13-10, 4.46 season, and at 36-years-old that may signal a decline. To make it even less attractive to the Red Sox or another team is the onerous $20 MM price tag and a potential $25 MM kicking in. The Red Sox simply have little desire to absorb that level of money nor I doubt the risk of a possibly declining player. The only way to make it work is the Cub contract generosity in picking up a large segment of the tab.