Mastrodonato: Jon Lester retires a winner, but Red Sox still look like losers

Every now and then a team can read the market correctly, make the most efficient move for the franchise and it can still be considered the wrong move.

In the case of Jon Lester, who announced Wednesday that he would retire after 16 big league seasons, the Red Sox did just that.

Lester should’ve been one of those rare players who spends his entire career for one team. He checked off all the boxes. He was beloved by the fanbase, active in the community, well-liked by his teammates and coaches, reliable, durable, playoff-tested and, perhaps more important than anything else, he wanted to be here.

For every $100 million the Red Sox have spent on free agents who had never before suited up for the home team in Boston — David Price, Pablo Sandoval and Carl Crawford totaled $454 million alone — the Sox could have eliminated the risk of the unknown and instead poured that money into keeping some of their best players who have proven to be successful in a market that isn’t easy to play in.

The case of Lester, who finished with an almost-Hall-of-Fame-worthy career and one of the best playoff resumes of all time, is a tricky one.

Break down the math and the Red Sox probably made the most efficient decision in trading him to Oakland before the July trade deadline in 2014, then letting him walk in free agency. He signed with the Cubs for six years, $155 million.

As we eventually learned, paying $25 million a year is a pretty good rate for a No. 1 or No. 2 starting pitcher. Lester pitched like an ace for two of those years, like a No. 2 for two more years and like a back-end starter for the final two years. If the Red Sox were looking for the most efficient deal possible, if they wanted to avoid paying an aging starting pitcher $25 million a season into his mid-30s, they succeeded.

Former general manager Ben Cherington explained the decision to a few of us in a hotel suite in San Diego during the 2014 Winter Meetings.

“I think in most deals, free agent or trade, sort of the last call you get to a point of pain,” Cherington said then, speaking generally. “Rarely does a deal happen without having to cross that last threshold.”

The Red Sox didn’t want to go past the threshold for Lester, and they saved a lot of dead money on the back end of that contract in doing so.

Here’s what they also missed out on: having a true Boston-tested ace atop their rotation in the final two years of David Ortiz’s career, the final year of which saw him rank as the most productive hitter in baseball before the Sox were eliminated from the postseason because — you guessed it — they were lacking an ace who could handle the playoff pressure.

Remember the “he’s-the-ace” season in 2015? The Red Sox learned some lessons, for sure.

Cherington was fired, Dave Dombrowski was hired and the team over-corrected by signing Price.

In retrospect, Ortiz should’ve pulled an Eric Weddle and come out of retirement for the 2017 postseason, when the Sox finally had an actual ace, Chris Sale, though Sale couldn’t get the job done in Houston, where the Alex Cora-assisted Astros were banging trash cans and hammering home runs off everybody, and the Sox were eliminated in four games.

Ortiz later made comments about how he wished he was there to play with Sale. He also made comments in 2014 about how the Red Sox were upset when Lester was traded.

Instead, Ortiz got to play his final year with Price, who notoriously did not like Ortiz and was rarely, if ever, found sharing a genuine moment with him when the cameras were off.

Price was largely a failure in Boston. And while he salvaged his tenure with an impressive playoff performance in 2018, he averaged less than 200 innings with an ERA of 3.84 and ERA-plus of 118, which made him an overpaid, mid-rotation starter. The Sox have been paying him $17 million a year to pitch for the Dodgers since 2020 and will do so again in 2022.

Would the Sox have won the World Series in ‘16 if Lester was there to buoy the rotation? It’s hard to say for sure. But they would’ve been a heck of a lot better.

Imagine all the good Lester would’ve done in aiding the development of some of the Sox’ young pitchers with another six years in Boston. And the work he and his family would have continued to do in the community (Lester was later nominated for the Roberto Clemente Award while with the Cubs).

Rarely does a fanbase get what it wants. It gets what the team decides to give.

Cherington wasn’t a bad GM. But like many modern-day GMs, Cherington chose the most efficient path and avoided moving into the “that last threshold” of pain to keep Lester in Boston after the Sox had botched negotiations in the springs leading up to his free-agent year.

Obviously, it was the wrong move. Even if the math says otherwise.