What Could’ve Been if the Red Sox Extended Jon Lester in 2014

Jon Lester

Six summers ago, John Henry and the Boston Red Sox made a deal that altered the trajectory of the franchise for years to come. At the 2014 trade deadline, the Red Sox traded Jon Lester to the Oakland Athletics after failing to reach an extension with the lefty the offseason prior. Today, Lester and his 3.59 career ERA are nearing the end of a six-year, $155 million contract with the Chicago Cubs.

Lester’s Potential Farewell to Wrigley

Lester was emotional after what may have been his final start at Wrigley Field after spending six years on the North Side.

“This year hasn’t been easy for a lot of reasons,” Lester said. “I’m not sitting here saying ‘woe is me’ because there’s a lot of people worse off than me. A lot of emotions coming into this. Don’t really know what to say, how to take it. A lot of uncertainties going forward.”

During his time in Chicago he’s sported a .639 winning percentage with a 3.61 ERA. Lester shines brightest in October, however; he’s posted a 2.42 ERA while helping the Cubs break the longest World Series drought in baseball. The signing of Lester has even been described as one of the best singings in Cubs history by some.

While hindsight is 20/20 and even John Henry has admitted that the team “blew it” when it came to not extending Lester, it’s interesting to think about what could’ve been if they had simply paid their guy as opposed to David Price or Chris Sale down the road.

2014 Contract Negotiations

Heading into the 2014 season the Boston Red Sox were on the heels of Jon Lester and David Ortiz leading them to one of the more unlikely championships in recent memory. In the 2013 regular season, the lefty went 15-8 with a 3.75 ERA. In the postseason he started five games and posted a 1.75 ERA. Two of the starts came in the World Series where only one run was let up on his watch. Lester had ascended into a bona fide ace in the league entering the final year of his contract.

As talks of an extension surfaced, the southpaw admitted he’d be willing to take a discount to remain in Boston. Lester came up through Boston’s system and had helped deliver two World Series titles. The team pushed the envelope a little too far, however, offering their ace a four-year, $70 million extension. The offer essentially ended all negotiations between the sides until that winter.

In April 2014, John Henry went on the record chastising teams who overpay for their players into their 30s. Lester, who was entering his age-30 season at the time, clearly was no exception to this. Henry cited this as why the team refused to give a respectable contract to their top starter.

Ben Cherrington went on to trade Jon Lester along with Jonny Gomes to the A’s for Yoenis Cespedes ahead of the 2014 Trade Deadline.

New-Look Rotation

The Red Sox won the title again in 2018. However, it’s tough not to think about what the rotation may have looked like if Lester had stuck around for six more seasons. The team went on the flip Cespedes to the Detroit Tigers for Rick Porcello in 2015. Porcello then extended with the Red Sox through 2019 making about $20 million per year. Moves that followed include signing Price to a seven-year, $217 million deal heading into his age-30 season. They also dealt Yoan Moncada for Chris Sale, and then extended him to a five-year, $145 million deal heading into his age-29 season.

It’s worth noting that Dave Dombrowski did take over for Ben Cherington late in the 2015 season. There may have been a change in philosophy, but it’s difficult to ignore Henry’s logic in April 2014 as to why they didn’t re-up Lester; they didn’t want to pay a pitcher big money heading into their 30s.

Life After Lester

The Red Sox went on to miss the postseason in both 2014 and 2015 without Jon Lester. They returned to October in 2016 but the Price and Porcello-led Red Sox got swept in the ALDS to the Cleveland Indians. A year later after acquiring Chris Sale the team saw a similar fate against the Houston Astros.

Lester, one of the best postseason pitchers in recent memory, was off helping the Cubs win the World Series in 2016. Meanwhile, the Red Sox were heading into October led by Price; at the time his postseason struggles were well-documented.

Sale was still a perennial Cy Young Award candidate and Price eventually straightened things out in the 2018 playoffs. However, it’s been far from a smooth ride with these two. Price got into confrontations with the Boston media on multiple occasions and often found himself on the injured list. Sale was far from his normal self in the 2018 World Series run and has been injury prone since.

If the team had just paid John Lester in 2014, it’s fair to wonder if they could’ve been the first team in the 21st Century with five World Series titles.

Main Photo: Embed from Getty Images