The pursuit of Jackie Bradley Jr., and the team’s general outfield approach

After a very quiet first few weeks of 2021, the Boston Red Sox finally started to make some moves this past weekend. They signed utility man Enrique Hernández and starting pitcher Garrett Richards in transactions that aren’t exactly major headline material but will have to suffice for now.

The signings of Hernández and Richards came hot on the heels of some more splashy deals made by other teams earlier in the week, with George Springer signing with Toronto and Michael Brantley re-signing with Houston. Springer and Brantley were both possible Red Sox targets, although it seemed unlikely either would join the team as we’ve seen the Red Sox be more conservative in their approach this offseason.

Springer and Brantley were two of the more high-profile free agent outfielders out there, which means teams (including the Red Sox) that are looking to upgrade that part of the roster have fewer options. But that doesn’t mean those options aren’t good ones. Even with Springer and Brantley signed, guys like Marcell Ozuna, Joc Pederson and Jackie Bradley Jr. are still looking for their next teams. Ozuna is the most high-profile guy left, and there is certainly an argument to be made for why the Red Sox should sign him, but Bradley feels like the more natural fit based on a number of factors, including cost and familiarity with the team. So why haven’t the Red Sox already re-signed him?

That’s a question we’ve been asking for a while now and I don’t just mean this offseason. Bradley has been an integral part of the Red Sox since he made his MLB debut in 2013, helping the team during two World Series title seasons (moreso in 2018, of course) while earning an All-Star nod in 2016 and winning a Gold Glove in 2018. He has always been a bit of an up and down player at the plate, but as that Gold Glove indicates, he’s been an exceptional defensive center fielder. Yet despite those accolades, Bradley, who was a first-round draft pick in 2011, was never given a long-term extension. Last winter, as he prepared to enter his final year before unrestricted free agency, he agreed to a one-year deal for $11 million with the Red Sox. It marked the fourth-straight season they juked arbitration with such a contract.

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Throughout 2020, there were a litany of whispers about Bradley’s future, but it seems clear that an extension was never really part of the discussions behind closed doors. Despite that, the Red Sox were interested in Bradley earlier this offseason — even though he didn’t get a qualifying offer — and that apparently remains true. So what’s the hold up?

The most obvious answer is money. MLB Trade Rumors estimates that Bradley will sign for a deal similar to the one Hernández just inked with the Red Sox, but there’s no way of knowing if those are the actual numbers being discussed behind the scenes. That may speak to why Bradley hasn’t been signed by any team, including the Red Sox, as many teams seem to be a bit reticent to spend on free agents, even with the market bearing out a bit better than initially expected. Obviously, coming to terms on a deal isn’t an easy process, so the actual machinations are also part of the delay. From the outside, it seems simple, but just going and signing any player takes more than picking up the phone once. But we are nearing February, so there is less room to ask for patience. That leaves a few other reasons Bradley hasn’t re-signed.

First, it is very possible he simply doesn’t want to come back to Boston. As I mentioned above, the Red Sox never really put much emphasis on signing him for the long term and that isn’t a great way to ingratiate yourself to a player. In addition, the Red Sox appear ready for a somewhat major (and potentially lengthy) rebuild. Bradley will turn 31 this year and may not be interested in playing for a sub .500 ball club for the next few years.

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That brings me to the next reason why the Red Sox haven’t re-signed Bradley yet. The team may simply have its eyes set on that rebuild and might not think Bradley fits with that process, especially with how they are building the outfield. Right or wrong, its certainly a possibility, as major adjustments to the outfield have been a trend in the organization the last 12 months. It’s quite the sea change for a team that seemingly had it all on that part of the roster just a few years ago.

At the end of the 2016 season, Mookie Betts had just finished as the runner-up for AL MVP, Bradley was coming off an All-Star season and Andrew Benintendi was a highly-touted prospect who performed very well in his first run at the MLB level. The harmony between the three continued into the next few years, including during the Red Sox’s 2018 title run. However, after Betts was traded last winter and Bradley was left to test free agency this winter, the Red Sox’s once mighty outfield isn’t what it once was. It could look even more different in the next few weeks, as rumors sprouted up this winter about Benintendi being on the trading block.

Since Benintendi hasn’t been dealt just yet, if the season started today, the starting outfield would likely be made up of Benintendi in left, Alex Verdugo in center and Hunter Renfroe in right. Such a makeup puts more of an emphasis on offense than defense, which isn’t exactly a bad thing, but its worth noting. Verdugo led the Red Sox in bWAR last season and ranked second in fWAR. However, he did most of that work as a corner outfielder, even if he displayed solid skills as a center fielder in Los Angeles. Benintendi has been on the downswing offensively and defensively the last couple years, and while he still has time to turn things around, that trend is worrying. Renfroe has a ton of pop in his bat, and he did produce an incredible 23 defensive runs saved in 2019, but that production was a bit of an outlier, so its likely he will be somewhat of a defensive downgrade in right field compared with Verdugo and Betts.

Looking further into the future, the Red Sox have prospects like Jeisson Rosario, Marcus Wilson, Jarren Duran, Gilberto Jimenez and Nick Decker on the horizon, with Rosario and Wilson already on the 40-man roster. With some of those names, most notably Duran, on the way up presumably sooner than later, a multi-year deal with Bradley could be seen as counterproductive to their development.

Those are at least some possible explanations for why Bradley isn’t already back with the Red Sox, and as times continues forward, it seems less and less likely that the Red Sox will re-sign him. If they don’t, the Red Sox may be looking at a continued overhaul of what was once considered one of the best outfields in baseball.