What if Jon Lester’s Red Sox Career Continued?

The Prologue

In 2014, Boston was at a crossroads with their franchise pitcher. Jon Lester’s Red Sox Career was in question due to his then upcoming free agency. He had claimed to be willing to take a “hometown discount” so he could stay in Boston. But when Red Sox brass reportedly offered him a 4-year/$70-million-dollar contract, the two sides never reached an agreement. Jon Lester's Red Sox Career

Lester stayed with the Sox for the beginning of the 2014 season and made the All-Star Game. However, the team was seemingly out of it at the trade deadline, and Lester was shipped to Oakland as a rental with Jonny Gomes in exchange for Yoenis Cespedes.

At the end of the season, Cespedes was traded to Detroit for Rick Porcello. Meanwhile, Lester still became a free agent. The Red Sox were in talks to re-sign him but faced huge competition from the Chicago Cubs. Thus, Jon Lester’s Red Sox career was in jeopardy.

Eventually, the Cubs won the bidding and signed Lester to a six-year, $155 million deal with a vesting option for a seventh year at $15 million. The move reunited him with both David Ross and Theo Epstein. John Lackey, who was also traded in July 2014, would join the club the following year.

What if Jon Lester’s Red Sox Career Continued??

But what if John Henry and Co. had signed Lester to a big deal of their own? Let’s say at around the same price the Cubs paid, or more.

Well for starters, David Price would either be a Yankee, a Cub, or a Cardinal.

Rick Porcello may or may not be on the roster. Depends on how comfortable they would’ve been with Lester, Clay Buchholz, and prospects like Rubby de la Rosa, Brandon Workman, and Anthony Ranaudo.

Only one of those guys (Workman) remains on the 40-man roster today. Eduardo Rodriguez, though still very young then, could have been another compliment.

Both Justin Masterson and Wade Miley wouldn’t have been acquired. Obviously, they were only placeholders until Price came along. But, of course, with Lester who needs Price?

Additionally, David Ross would’ve stayed with Boston for the remainder of his career. He and David Ortiz would’ve retired at the same time.

Dave Dombrowski wouldn’t have been hired because the Ben Cherington would’ve had less pressure to succeed if he had kept Epstein’s guys, like Lester, around to help. Likewise, I believe the Sox would’ve won more games in 2015 with one ace as opposed to five #4 starters.

So would the Cubs win the World Series in 2016 without Lester? Nope.

Instead, I bet Theo would’ve chased Price or Zack Greinke in the 2015 offseason. Especially if Lester had slipped away and the team failed to reach the NLCS. The ’16 Cubs would then, of course, have a similar campaign and reach the postseason. Only to lose Game 5 of the NLDS to the Giants with David Price on the mound.

The Giants would’ve made the World Series and played the young and exciting Red Sox (of course). Jon Lester would pitch Game 7 against Madison Bumgarner in an epic duel. Almost as good as the Cubs-Indians duel.

It’s a shame that the team who drafted, developed, and gave him everything didn’t resign him. Jon Lester is a hero to many – and his resilience through cancer, dominance on the mound, and consistent sportsmanship is legendary.

We may never know.

Red Sox Fans Look Ahead to the Trade Deadline

With Memorial Day behind us, attention is slowly turning towards the trade deadline in Major League Baseball. For perhaps the first time since 2013, the Red Sox are in a strong position as the calendar flips to June, which means they should be buyers in the market, looking to add pieces for a championship run rather than selling them to assist a rebuild.

Trade deadline

Right now, Dave Dombrowski doesn’t need to worry about offense or defense. The Red Sox lead baseball in almost every offensive category, and the everyday lineup could produce some historic numbers before the season is over. Mookie Betts, Jackie Bradley Jr., and Xander Bogaerts have taken another step forward. Dustin Pedroia and David Ortiz are turning back the clock with tremendous performances. And even unheralded guys like Travis Shaw and Christian Vazquez have taken their turn leading this team. All around the diamond, the Red Sox are really solid with the leather, which is also fun to see.

So, we come to the one area where Boston must improve: pitching. At this point, almost everybody on the planet must know that the Red Sox lack elite rotation depth. Boston starters have a 4.57 ERA, thanks mostly to Clay Buchholz and Joe Kelly. That ranks 21st in baseball, and must improve if Boston is to compete for a World Series championship.

What Can the Red Sox Give Up at the Trade Deadline?

We’ve already heard enough about potential trade targets for the Red Sox, and those discussions will intensify in the coming weeks. By the time July arrives, you will likely be tired of hearing about Sonny Gray and Julio Teheran, so it’s time to take a different approach. Let’s look not at what the Red Sox can acquire at the trade deadline, but rather what they can actually give up. Who, exactly, are their most realistic trade chips?

By hiring Dombrowski, signing David Price and acquiring Craig Kimbrel, the Red Sox signaled a shift in philosophy, away from prospect conservation and toward a win-now mentality. However, we live in an age where sustainable contention is only achievable by delivering constant waves of young talent to the major league roster. Therefore, it’s still safe to assume that certain elite prospects are untouchable in trade deadline negotiations. Personally, I would include the following players in that group: Betts, Bogaerts, Yoan Moncada, and Andrew Benintendi.

Due to a very deep system, that still leaves plenty of chips with which Dombrowski can work. Down on the farm, guys like Rafael Devers, Anderson Espinoza, Brian Johnson and Michael Kopech may be expendable, although the latter three are promising pitchers in an organization starved of talent at that position. Elsewhere, fringe big leaguers like Henry Owens and Rusney Castillo may also be better utilized as trade deadline currency at this point.

Yet, at present, I think the Red Sox’ biggest trade chip is Blake Swihart. He possess a really strong bat with plenty of upside, but has struggled defensively behind the plate. Given the dearth of catching talent, many teams would overlook that deficiency in favor of his offense, but the Red Sox are in a position where their lineup is so dominant that carrying an elite defensive catcher like Christian Vazquez is preferable. That leaves Swihart without a position and, perhaps, without a future in Boston.

Ultimately, Dombrowski has many options as he attempts to tweak and improve his team. For that, he can thank Ben Cherington and – to a lesser extent – Theo Epstein, who did tremendous work stockpiling such a wide array of young talent. Now might be the time to flip some of these prospects for a true difference-maker in 2016 and beyond. With young stars blooming at the major league level, the future has finally arrived for the Red Sox. The trade deadline is an opportunity to grasp it and take full advantage.

The Red Sox are Losing at the Worst Possible Time

In a season of perpetual disappointment, the Red Sox chose the worst possible time to embark on a long losing streak. Just as momentum was building, and fans began to see a glimmer of light, Boston lost two of three to New York prior to the All-Star Game, before stumbling to five straight defeats to start the second half.

All told, John Farell’s hapless team has lost six consecutive games, falling back to 42-52,Red Sox ten games adrift of the division-leading Yankees. Cautiously optimistic just two weeks ago, the Red Sox now have the worst record in the American League. This latest slump may be terminal.

The $166m Sox have been outscored 29-7 in their last five games. In fact, Boston’s -66 run differential on the season is third-worst in baseball, behind only the woeful Phillies and spluttering White Sox. Such a stat is emblematic of the Red Sox’ struggles, and obviously descriptive of a painfully unbalanced baseball team.

However, at this point, it’s difficult to see Ben Cherington making any moves to improve his lopsided roster. According to Fangraphs, the Red Sox have just a 2.1% chance of winning the AL East, while the likelihood of securing a Wildcard spot rests at 5.7%. For a front office that adores statistical analysis, those are particularly damning numbers. And, no matter how frustrated Red Sox Nation becomes, this hierarchy simply won’t mortgage the future to acquire a player who, at best, will enhance their chances of reaching a sudden-death Wildcard playoff from practically impossible to not gonna happen.

Now, the more likely scenario is the Red Sox selling off any excess big league pieces. At this point, Boston can only hope to retool and begin planning for 2016. Despite chronic batting average problems, Mike Napoli may interest a team hungry for power. Similarly, Shane Victorino may pique the interest of a contender searching for speed and experience atop its batting order. Even Koji Uehara may be dangled, tempting innumerable teams looking for bullpen help.

In the bigger picture, perhaps moving these ageing players would be beneficial to the Red Sox, who could finally grant extended playing time to Rusney Castillo, Jackie Bradley Jr and Allen Craig, evaluating once and for all what those players actually are, and where they actually fit moving forward.

Yet, even this may be troublesome. It remains to be seen whether Ben Cherington has the energy and wherewithal to blow up his roster for the third time in four seasons as Red Sox GM. More to the point, will John Henry allow him to do so, and risk the crown jewel of his business empire becoming synonymous with failure, false dawns and fire sales?

Regardless of the next step, the Red Sox once again find themselves in a sorry state. Once again, this team appears dead before August has even arrived. And, amid an ocean of statistics and records speaking to this team’s wide-reaching ineptitude, that may be the most resounding reality of all.