By Michael Hurley, CBS Boston

BOSTON (CBS) — On its face, it’s simply incongruous for the Red Sox to be the team that has to give up an MVP-caliber player because they just cannot afford his next contract. Typically, it’s been the Red Sox — or Yankees, Dodgers, Cubs, etc. — that swoops in and takes another team’s star player, breaking the hearts of fans of those small-market teams that just can’t keep pace with the spending of MLB’s top dogs.

And to be sure, when you compile the list of big-money contracts the Red Sox have dispensed like Pez over the past two decades, you’d most likely find it quite peculiar that an actual MVP, an actual World Series champion, an actual future Hall of Famer and an actual home-grown talent marks the point of demarcation where the Red Sox decide to put the clamps on the purse strings and ship him out of town for pennies on the dollar.

And right now? You’d be right to feel that way. This is not normal. And it’s not great.

But to focus only on Tuesday night’s deal with the Dodgers is to ignore a larger picture — a picture that also includes the dumping of roughly half of the $96 million owed to David Price over the next three years. It’s a larger picture that shows a number of poorly conceived and overinflated contracts that were handed out with too much ease by both Ben Cherington and Dave Dombrowski before ultimately being signed by John Henry.

It was a series of decisions that got the Red Sox into this luxury tax pickle, and if you really wanted to find an origin point, you could look directly back to the offseason following the 2013 World Series. That was the time that the team, led by Henry, embarked on an age of a new philosophy, one that abided by the principle that teams should not spend money on pitchers over 30 years old.

Thus, the Red Sox deemed Jon Lester to be expendable. And that is where the road to trading Mookie Betts began.

The Winter Of 2013/14

Through the first eight years of his career, Jon Lester proved capable of accomplishing what hundreds upon hundreds of players before him could not: Performing in Boston and winning World Series titles.

Fresh off a 2013 postseason during which he went 4-1 with a 1.56 ERA en route to winning his second championship with the team, the future looked bright for Lester and the Red Sox.

Unfortunately for Lester, he was mere months away from turning 30 years old, and thus, the Red Sox would not be interested in committing to him in the long term.

Here are Henry’s exact words, from April of 2014:

“Virtually all of the underpaid players are under 30, and virtually all the overpaid players are over 30. Yet teams continue to extravagantly overpay for players above the age of 30.”

From that statement, it was pretty clear that even though Lester was willing to take a discount to sign long-term with the Red Sox, the team inexplicably would not be interested.

The Red Sox reportedly only offered Lester roughly $70 million over four years, an “offer” that existed only to inform Lester and his agents that the player’s future would not be in Boston.

So in July of 2014, with the Red Sox falling toward a double-digit deficit in the AL East, the team traded Lester at the deadline, instead of making him play out the string for a last-place team before departing via free agency.

Thus kicked off a series of events that led to the Red Sox running their operation from a reactive position instead of a proactive position.

The Failure Of 2015

By trading Lester, the Red Sox were able to bring in Yoenis Cespedes, who was flipped that offseason for Rick Porcello.

Porcello was young, entering his age 26 season in 2015, so the Red Sox happily dedicated a four-year, $82 million contract extension to him shortly after acquiring him.

Porcello did win a Cy Young and a World Series during his tenure in Boston, but he also compiled a 73-55 record, a 4.43 ERA and a 1.256 WHIP in those five years. For the Cubs, Lester has posted a 74-41 record, a 3.54 ERA and a 1.242 WHIP during that time, with a second-place Cy Young finish, an NLCS MVP and a World Series title to his name.

At comparable prices, Lester has been the better picture.

But to compare Porcello directly to Lester is to miss the point entirely. The point is that the 2015 Red Sox, happily avoiding carrying Lester as one of those pesky overpaid players over the age of 30, went 78-84. After an offseason during which they committed $183 million to Pablo Sandoval and Hanley Ramirez, they finished in last place. Again. For the second straight year.

Considering their financial commitment to the team, consecutive last-place finishes in a division that included the low-budget Rays was simply unacceptable.

So, in the eyes of ownership, it was time to reverse course.

David Price

In the winter of 2014, it was simply not an option for the Boston Red Sox to commit to a pitcher over the age of 30. Even if that pitcher came up through the system, beat cancer, won a World Series as a role player in year two and as a borderline MVP in year eight, and carried himself with professionalism and maturity at all times, the Red Sox simply would not take on a long-term contract with such a player.

In the winter of 2015/2016, it was time to throw that philosophy in the trash.

The team decided that it was time to sign David Price to a seven-year, $217 million contract. He was 30 years old.

So in the offseason prior to the 2014 season, the Red Sox deemed Jon Lester worth just $70 million over only four years. Two years later, they deemed David Price worth a $217 million commitment over seven years.

It may have been possible that witnessing Lester help carry the Cubs to a World Series victory, after a season where Lester made the All-Star team and finished second in Cy Young voting, contributed to that change in philosophy.

Whatever it may have been, the Red Sox clearly committed to the wrong pitcher at the wrong time for the wrong dollar amount. (The Red Sox reportedly outbid the Cardinals by $30 million.)

Price, 2016-19
42-24, 103 games, 98 starts
3.84 ERA, 1.204 WHIP
588 IP

Lester, 2016-19:
63-29, 127 games, 127 starts
3.59 ERA, 1.276 WHIP
736.2 IP

Price, Postseason, 2016-19:
3-2, 9 games, 6 starts
3.75 ERA, 1.250 WHIP
36 IP

Lester, Postseason, 2016-19:
3-1, 10 games, 8 starts
1.93 ERA, 0.929 WHIP
56.0 IP

Price, Cost, 2016-19:
$121 million

Lester, Cost, 2016-19:
$85 million

Price, Remaining After 2019:
Three years, $98 million

Lester, Remaining After 2019:
One year, $15 million
(plus a $25 million mutual option in 2021, with a $10 million buyout)

Letting Lester go was the wrong move. Signing a lesser pitcher to a bigger deal two years later to try to atone for the mistake was a worse move.

And ultimately, being saddled with the prospect of owing $98 million to a pitcher who’s averaged just 21 starts and 119 innings over the past three years became a major issue for a Red Sox team suddenly in need of slashing payroll.

Other Reactions

Of course, one bad contract would not be able on its own to sink a team with pockets as deep as Henry’s. So if the team had only whiffed on the Price deal, it would have hardly made a dent in the overall efficiency of the billion-dollar yacht that is the SS Red Sox.

Alas.

Most recently, you could look to the Chris Sale deal. Now, anyone who’s observed Sale throughout his career can’t help but admire him. He not only is electric on the mound, but he brings the type of mentality that is rare in sports these days.

So make no mistake: Chris Sale rules.

But, he also has thrown the baseball very, very hard for a very, very long time. His physical structure does not inspire tremendous confidence in his long-term health, and his career-long trend of getting worse as seasons enter August and September only heightened those concerns.

So, with the Red Sox entering the final year of Sale’s contract last year, they faced a choice: Let him play out the final year to exhibit his worth to the other 29 clubs who could then sign him as a free agent, or commit big dollars to him in a multi-year contract.

By now, you know that the Sox chose option B, and it thus far looks quite bad. Sale made just 25 starts and pitched just 147.1 innings in 2019, his lowest totals since becoming a full-time starter in 2012. That’s ominous. The team is now committed to Sale for four more years at an average of just under $29 million per year, which, likewise, does not look spectacular at this very moment.

And to get a better understanding of what Henry and the Red Sox were thinking when they inked Sale to that deal, it’s worth looking at the owner’s quotes from last spring training, when his mind was on … Jon Lester.

“I think we blew the Jon Lester [negotiations],” Henry said last February. “We blew re-signing him in spring training.”

One month later, Sale had his long-term extension.

Count that as another reaction to the misjudgment on Lester, one that furthered the Sox into luxury tax hell one year ago.

Other reactions?

After seeing Jose Abreu and Yasiel Puig get off to tremendous starts, and after seeing the potential of Yoenis Cespedes firsthand, the Red Sox were not going to miss out on another Cuban sensation. So the team went out and guaranteed $72.5 million, sight unseen, to Rusney Castillo.

Suffice it to say, with Castillo now well-established in Triple-A, the Red Sox got the wrong guy. For the wrong price.

There were also some sentimental signings made by Dombrowski coming off the 2018 World Series win, contracts that never passed the sniff test, even in the champagne hangover of the championship. Though it was only for $6.25 million and one year, signing Steve Pearce never made sense. In a much larger problem, signing Nathan Eovaldi for a four-year, $68 million deal was an egregiously errant judgment for a professional baseball official to make.

The early returns on that Eovaldi investment? He made 23 appearances — just 12 starts — and posted a 5.99 ERA. The player with two Tommy John surgeries in his past developed elbow issues. Whether that improves or gets worse in the coming years is the $51 million question for the Red Sox.

There have been good deals along the way. Xander Bogaerts‘ extension is a steal, and the J.D. Martinez signing was arguably the key move for the Red Sox to win the 2018 World Series. And prior to the career-wrecking injuries, Dustin Pedroia‘s long-term deal looked like it would be a tremendous value for the Red Sox, keeping their guy at their price for a long time.

Alas, that deal did not end up panning out, nor did the possibility of the Red Sox signing Mookie Betts for a similar time period. A series of bad decisions and bad contracts pushed them over the threshold for the competitive balance tax, putting them in a position for 2020 where they needed to both shed salary and restrict themselves from committing big money and several years to a player who objectively deserves that type of contract.

And while all of the team’s financial issues at the current moment cannot be ascribed to one singular decision, the choice to shoo away Jon Lester in 2014 looks to be the right starting point to try to figure out how the Red Sox ended up here.

You can email Michael Hurley or find him on Twitter @michaelFhurley.

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