Jon Lester Rewards Cubs Faithful With Free Beer

  • Jon Lester, now a free agent, bought $47,000 worth of beer for Cubs fans as a farewell after six years with the organization
  • Lester, 36, should have plenty of suitors on the open market despite a down 2020 season
  • Cubs look to bounce back from 2020 Wild Card round upset with mid-range odds to win the 2021 World Series

Lester Buys a Round for Cubs Fans

Have a cold one on Jon Lester.

The long-time big-league southpaw spent the last six seasons with the Chicago Cubs, and he made sure to reward the Cubs’ faithful as he enters free agency this offseason.

Lester offered to buy anyone who was up for it their first round of Miller Lite at a select four bars in Chicago. Lester tweeted out his tab which included a 34% tip, which he wore with the Cubs after rocking No.31 during his Red Sox tenure up until 2015 when he signed a six-year deal with the Cubs.

The tab included $31,082.63 worth of Miller Lite purchases and another $16,012.27 in gratuity.

In fact, the Monday tweet comes on the four-year anniversary of helping the Cubs win the 2016 World Series, snapping a monster 108-year drought in the process. Lester took home co-MVP NLCS honors alongside Javier Baez as he worked to a 1.38 ERA across two starts against the Los Angeles Dodgers.

“Was kind of brainstorming on what we wanted to do [for the fans],” Lester told ESPN 1000 in Chicago on Friday. “Couple buddies and I were talking and we seemed to always come back to this.”

Lester signed a six-year, $155M deal with the Cubs prior to the 2015 season and won 77 games for them in that time.

Plenty of Interest Ahead in Free Agency

Despite the Halloween weekend gesture, Lester’s stay with the Cubs isn’t guaranteed to be finished.

“Since Day 1 it’s been awesome to be a part of,” Lester said. “They have made my family feel like family and accepted us from the beginning. It’s been a fun ride, and hopefully the ride is not over,” Lester said.

That said, the Cubs predictably turned down his pricey $25M option over the weekend, but there is still a chance the Cubs could bring him back on a cheaper deal for next season and potentially beyond.

“I know there is some doubt as far as the money that’s out there, but I would like to think we can definitely get this thing done,” Lester said. “I think it’s going to be a long offseason for everybody.”

Not only the Cubs and most every other club in baseball feeling a financial pinch this offseason, but the team was already in the midst of limiting payroll as they did last offseason without any major splashes on the open market. The tightening of the purse strings also put the likes of Kris Bryant, Javier Baez and Willson Contreras into the trade rumor mill as they approach free agency within the next few of seasons. Bryant and Baez are free agents after the 2021 season and Contreras after the 2023 campaign.

As we embrace for plenty of short-term deals in free agency this winter, Lester should be in high demand despite a down 2020 season. At 36, one-year deals from here on out were probably the most realistic scenario regardless of the league’s current economical picture.

Lester turned in a 5.16 ERA/5.14 FIP last season to go along with a 6.20 K/9, all of which represent career-lows for the 15-year big-league veteran.

That said, he also posted a 3.32 ERA as recently as 2018 and has been consistently reliable in his big-league career, posting a sub-4.00 ERA in nine of his 15 seasons.

Given the major rotation needs in Boston, a potential reunion with his old club is going to gain attention over the course of what should be a slow-moving offseason. That said, there are plenty of contenders who could be in the market for rotation help with the likes of the Los Angeles Dodgers, New York Yankees, San Diego Padres, Atlanta Braves, New York Mets and Houston Astros all likely in the market for short-term rotation help and the proven playoff performer Lester will certainly gain some attention with those clubs moving forward.

Otherwise, it’s difficult to envision Lester signing with any non-contender not named the Red Sox.

Cubs Looking to Rebound

The 2020 regular season was largely a success for the Cubs despite an offensive that tailed off and a rough start for the bullpen.

The Cubs began the season 11-2 thanks to some elite starting pitching and a hot start at the plate, but Bryant and Baez mostly struggled the rest of the way and the Cubs finished the season at 19th with a .309 wOBA. They posted a second-ranked .359 mark in the season’s opening week, but it was mostly downhill from there.

The offensive issues persisted into the postseason as the Cubs scored just one run in their two-game Wild Card round sweep at the hands of the underdog Miami Marlins. They also managed just nine hits in 18 innings.

They entered the 2020 season with +2500 World Series odds, but currently sit +3300 to win the 2021 World Series, as per BetOnline.

According to Spotrac, the Cubs currently have $150,485,000 committed to next year’s roster, third-highest in the league behind only the Dodgers and Yankees. Interestingly, at the time of this writing, Lester is the No.1 trending player on Spotrac’s website.

The lofty commitments currently on the books combined with a severely diminished economic picture and a 2019 offseason in which they limited spending doesn’t exactly put the Cubs at the forefront of teams looking to make a big splash this winter.

It probably won’t take a big offer to retain Lester on the heels of a down 2020 season, although given the vast amount of suitors for a proven postseason performer likely willing to accept a modest sum on a one-year deal and I think Lester ends up elsewhere this winter.

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