When looking back at Theo Epstein’s history—a history that now includes a complete overhaul and turnaround of a moribund Chicago Cubs franchise—unless you’re nitpicking, there’s little to criticize. However, if there is one aspect during Epstein’s run as a general manager in Boston one could pounce on, it’s a somewhat spotty track record with free agents.

With questionable moves from their past likely lingering in the back of their minds—Julio Lugo and Carl Crawford stand out in particular—both Epstein and Jed Hoyer have spent plenty of time in Chicago lamenting the fact that free agency is often looked upon as a ‘necessary evil’ of sorts. Their first big signing on the North Side, Edwin Jackson, stands out as one of their more prominent failings since joining the Cubs organization four years ago. But for the most part, by design, this group has avoided big free-agent signings. That changed last offseason when they made one of the bigger splashes of the winter by snagging Jon Lester to a six-year, $155 million deal. The spending has continued this December with the additions of John Lackey, Ben Zobrist, and most recently Jason Heyward.

“We saw it as a real unique opportunity. We saw Jason as an impact player because of how talented is in all the different phases of the game,” Epstein said, listing off Heyward’s defensive skills, baserunning acumen, and ability to get on base and grind out at-bats as a package that drew the Cubs to him. “He just does all the little things that go into winning baseball games and he impacts the game in lots of obvious ways and subtle ways as well. And then you put on top of that his age, that he’s just entering his prime and has a chance to be an even better player than he has to this point in his career.”

Those little things that Epstein mentioned, they aren’t the types of skills that normally garner $150-plus million contracts. And inevitably, when going against the grain like some view this contract, there will be criticism. Even before Heyward signed with the Cubs,’s Tom Verducci showed there were those who wondered if he would be worth the big contract that was likely headed his way. Matt Trueblood countered that piece and other opposing opinions and explained why he would be worth it; and nearly two weeks ago, I addressed why he was a perfect fit for the Cubs. Epstein and the Cubs clearly see the fit as well.

This isn’t the first time Epstein was in charge of a front office that viewed a player a little differently than many around the game.

“We signed J.D. Drew in Boston with a somewhat similar skill set; a great deal of his value was tied to his ability to play well above-average right field and get on base at a high clip,” Epstein said when asked about paying for untraditional skills. “He didn’t necessarily have the home run and RBI numbers to placate everybody. But that’s the way it goes. We want to add players who are going to help us win the World Series.”

Drew did just that, hitting .314/.352/.431 during the Red Sox World Series run in 2007, contributing a critical grand slam the ALCS against Cleveland. But I’m getting ahead of myself, this isn’t about whether Drew was actually worth the five-year, $70 million deal the Red Sox gave him (he probably was, as shown displayed by his 11.4 bWAR/12.7 fWAR/9.3 WARP). It’s about the reaction to both the signing and Drew’s tenure in Boston.

Murray Chass, writing for the New York Times, discussed how many around the league assumed that there must have been tampering involved for Drew to opt-out of his contract two years into a five-year deal with the Dodgers. In the article, there were some sources who claimed Drew had done nothing to indicate he’d opt out, so the decision came as a surprise and many suspected tampering. And while all of the anecdotes in the piece may have had some truth to them—I honestly couldn’t say—what struck me was how there was a spin that Drew couldn’t possibly be worth such a deal.

A few days later he left the Dodgers, walking away from a guaranteed $33 million. Drew is a talented but fragile player who has been on the disabled list seven times in his eight-year career and has never played as many as 110 games two years in a row.

“I don’t think he’s the kind of player who would walk away from $33 million without some idea of what was out there,” a baseball official said.

Yes, Drew had a history of injuries, but the above is some artful cherry-picking. In the 2006 season Drew had 146 games and accumulated 5.2 WARP. Indeed, in the season prior he played just 72 games after suffering a broken wrist and still managed to put up 2.6 WARP during that time. But just the year before that, he delivered an 8.2 WARP in season that saw him finish sixth in MVP voting, helping him earn that initial deal with the Dodgers. Drew was undoubtedly an injury risk, but to suggest that it wasn’t clear he could top the remainder of his Dodgers deal on the open market—even at the age of 31—showed quite the lack of understanding of valuable skill set.

And so it continued. Drew would have a solid five seasons with the Red Sox, with the backend of the deal being the real albatross, something we’ve all grown to accept as a reality when teams hand out multi-year deals to 30-plus-year-old players. But many wouldn’t even see those first three as a success. Drew never hit over .280 or drove in more than 68 runs during his stint in Boston, thus he—and in turn, Epstein—garnered quite a bit of criticism during those five years.

Just prior to his 2007 postseason heroics, Drew’s contract was referred to as “curious” and just six months into the deal, he was already “considered a colossal bust” by some. Not just a Lilliputian bust mind you, but one of the colossal variety.

After a few seasons, questioning whether Drew brought enough to the table to earn his contract became so common place that Epstein was actually asked during a radio interview if he got tired of defending Drew. Epstein responded by talking about how Drew’s at-times lackadaisical demeanor can turn some onlookers off, and felt Drew was “an interesting case study in the way fans and media perceive certain players.”

Epstein then wrapped us his response quite emphatically:

Am I annoyed to have to defend him? No. But I like justice. So when players are picked on unfairly, when they are doing well, it shouldn't be ignored.

The whole interview, conducted in October 2009 when Drew was wrapping up a season in which he posted a .294 TAv, was quite fascinating as it includes Epstein citing a study on how body language affects perception of a player, a nice rant against the value of RBI, and how too many still undervalue the ability to avoid making outs.

The debate on Drew raged on for years, with some writers going out of their way to show he didn’t deserve the criticism and others still taking pot shots years later when talking about his brother.

And so here we are, nearly a decade after the Drew signing with another unconventional superstar in the spotlight. Heyward doesn’t have the same perception issues that Drew did, he’s also just 26, has a very minimal injury history, and while Drew was considered a strong defender in right at the time, Heyward is accepted as elite by both scouts and advanced stats. Yet we still see columns like the above-linked that has many baseball executives and managers wondering if Heyward is actually worth a big-time contract. And it makes me wonder, how far have we really come over the last decade with regards to valuing the important aspects of the game?

Perhaps Chass and his many sources had a point; maybe there wasn’t a robust market for Drew back then because his skill set just wasn’t appreciated. I asked Epstein if he felt front offices around the league had evolved over the last decade, but he demurred, likely not wanting to talk about other teams and how they run their organizations. But while Epstein won’t say it, I will: He and his front office have been ahead of the game. No, he wasn’t alone back in 2006, but the number who see it his way has only grown since then.

“There’s a side that rewards you for staying healthy and being a good person in the clubhouse and bringing things to a game on a daily basis,” Heyward said when asked if he appreciates that he’s one of the first to really have such a unique set of skills valued around the league. “And you just want to be appreciated for that at the end of the day.”

There were few who doted upon Drew during his time, that’s not the case with Heyward. While he may not be living up to the Hank Aaron comps he received while coming up through the Braves system, he’s still proven to be a special talent. Yes, there will always be those around the league like the ones Verducci found and columnist or radio hosts who point to Heyward’s batting average or RBI total when being critical rather than appreciating all the unique ways in which he impacts the game.

And while all may not recognize what he does, there’s no denying the number who do is growing. Heyward’s distinctive play was highly sought after this winter as he checked off many of the boxes that make teams less weary about dipping into the often choppy free-agent waters, something that may not have been the case just a decade ago or two ago. Players like Heyward don’t reach free agency very often, certainly not at his age, but perhaps when someone similar does do so down the line, there will be even fewer who are surprised by the large amount he collects on the open market.

Thank you for reading

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So he'll be frustrating but hit a grand slam in the World Series and win over most fans, then Sahadev Sharma will refer to it as the 184 million dollar grand slam ,and all will be well.
Well, the whole point is that Drew was frustrating only to people who don't really understand value of a player and only look to batting average and RBI. And Heyward is better. So... No.
There is also the fuzzy, but still very real, calculation of addition by subtraction, in the sense of Heyward no longer being on the Cardinals. Though this probably just clears the way for Steven Piscotty to turn into Stan Musial.
Sorry, that's Steven with a "ph" - Phsteven Piscotty.
I believe you mean wary in the last paragraph?
I'm getting weary of this debate.