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This offseason, David Stearns is taking his greatest risk yet

Stearns has never been afraid to be unconventional. Now he’s taking that boldness to the next level.

MLB: General Managers Meetings Mark J. Rebilas-USA TODAY Sports

If there is anything that we have learned about David Stearns as the top executive of the Milwaukee Brewers, it’s that he is not afraid to make moves that are risky and don’t seem to make a whole lot of sense at first.

In January 2018, he swung a blockbuster trade to acquire Christian Yelich from the Miami Marlins. While it came at the cost of top prospect Lewis Brinson, an outfield of Ryan Braun, Yelich, and Domingo Santana — who was coming off of a breakout 2017 season — sounded great to Brewers fans.

Then just a few hours later, Stearns inked Lorenzo Cain to a franchise-record contract worth $80 million over five seasons. Some fans were excited, but others were confused. It seemed like an oddly redundant move and perhaps an unwise use of resources. It created what appeared to be a logjam in the outfield. Either Braun or Santana, both of whom were productive players, now looked like the odd man out.

During that same season, Stearns identified a need in the infield. Instead of acquiring a second baseman, he made a deal to bring Mike Moustakas, a third baseman, to Milwaukee. Travis Shaw, who stands six-foot-four and tips the scales at 230 pounds, was going to move to second base, a position he had never played in his life.

The following winter, the plan was to move Shaw back to third base and sign an actual second baseman. Instead, Stearns reunited with Moustakas, but Shaw wasn’t going to continue playing at the keystone. For the second consecutive season, Stearns planned on converting a career third baseman into a second baseman.

Stearns has also left fans scratching their heads with his restraint against signing a big-name starting pitcher. In each of the past two offseasons, starting pitching looked like a need for the Brewers, yet Stearns preferred to search the bargain bin for cheap rotation additions while relying heavily on Craig Counsell’s excellent bullpen management skills.

Those risks pale in comparison to what has happened to date this offseason.

Re-signing Yasmani Grandal should have been top priority. He’s now a member of the Chicago White Sox for the next four seasons at the same annual value as his salary from last year. Drew Pomeranz is a San Diego Padre. Mike Moustakas is a Cincinnati Red. Eric Thames had his contract option declined despite posting a solid 118 wRC+ across three seasons in Milwaukee. Junior Guerra pitched 83 productive innings as Mr. Do-It-All out of the bullpen, yet he was non-tendered. The front office decided they’d rather not bank a projected $4.7 million on a Travis Shaw rebound season. Chase Anderson and Zach Davies have been traded, and serviceable back-end starters Jordan Lyles and Gio Gonzalez are free agents. The Brewers are reportedly willing to listen to trade offers for fireman Josh Hader.

Opinions on each of these events vary. The Brewers appeared to be hesitant to go a fourth year with Grandal, but you can easily make a case that they should have gone out of their comfort zone to retain him. He’s been baseball’s best backstop for the past five seasons, and there’s evidence that he won’t decline as badly as one might expect. However, there are explanations for many of the decisions Stearns has made to date. Maybe he didn’t want to give Pomeranz a long-term deal based on a small sample size. Maybe he projected Moustakas’ low-OBP profile to age poorly. Maybe Chase Anderson is replaceable. Maybe Zach Davies’ 5.30 DRA and career-worst strikeout and ground ball rates hint that he’s due for regression and selling high was the right move. Maybe a bounce-back candidate like Justin Smoak or CJ Cron will provide more value than Thames next season at a lower price.

Whether you agree or disagree with the decisions that the front office has made thus far, the fact of the matter is that a significant portion of the roster is being turned over right in the middle of the team’s window. Case in point: with Orlando Arcia’s future unclear, there is a strong chance that Keston Hiura may be the only returning starting infielder from last season. Each of positions one through six will be occupied by a different player than the one who stood there on Opening Day of 2019. Brandon Woodruff and Adrian Houser may be the only returning rotation fixtures, and while both look the part of legitimate big-league starters, neither made a full season’s worth of starts last year. With players like Moustakas, Thames, Guerra, Grandal, and potentially Gonzalez gone, the Brewers are now without several players who were significant components of the clubhouse culture that had developed over the past few seasons in addition to losing the value that they provided on the field.

As a result, it’s easy to wonder what’s going on and begin to doubt Stearns. Bob Nightengale reported that the team is expected to reduce their payroll next season, which would be a highly disappointing development in the midst of a contention window. It’s not that difficult to assume that Milwaukee is actually beginning a tear-down.

However, Stearns promised on Monday night that the team intends to remain competitive, and he noted that there’s plenty of time left to make moves and build a strong roster.

Stearns is right in saying that there’s plenty of time left, and no one should be pressing the big red panic button at the beginning of December.

The Brewers have now cut their projected payroll down to roughly $70 million, which gives them in excess of $50 million to spend before reaching last year’s Opening Day payroll. Considering that they have Christian Yelich in his prime, Hader anchoring the bullpen, Woodruff and Hiura emerging as potential stars, and several positions to fill, they should be spending even more than they did last offseason.

There are plenty of free agents available. Anthony Rendon or Josh Donaldson could be Milwaukee’s new third baseman. They would come with high price tags, but the Brewers could easily fit them into their payroll now and for the foreseeable future if they wish to bring in a high-caliber player for the hot corner. Didi Gregorius and Howie Kendrick are available as well and won’t be demanding contracts that would break the bank.

This year’s starting pitching market looks stronger than those of years past, headlined by Gerrit Cole and Stephen Strasburg, supplemented by others like Hyun-Jin Ryu, and rounding out with veterans like Madison Bumgarner and Dallas Keuchel who have shown that they can still be effective. A reunion with Lyles, Gonzalez, or both remains a possibility.

Will Harris has arguably been baseball’s most consistent reliever over the past five seasons. The same went for Dellin Betances before injuries limited him to just one game last year. Blake Treinen is an intriguing bounce-back option.

The Brewers have seen their income grow substantially over the past few seasons, and every MLB team gets a good chunk of change annually through revenue sharing. Furthermore, Mark Attanasio is a rich dude. While we have no way of knowing exactly how much the Brewers have to spend, we can work to connect as many dots as we’re able to.

There was a good chance that the club could have already afforded to add without clearing all of the salaries that they have through trades, non-tenders, and letting their free agents walk. But now that they have in fact done that, it is crystal clear that the Brewers have loads of money to spend. There are players out there to spend it on, and they need to spend it on them to keep the team competitive. It’s not unreasonable to ask that Attanasio continue his trend of opening the checkbook and start the 2020 season with a new record high for payroll.

Many of the risks that Stearns has taken have worked out. Yelich turned into one of the best players in baseball. Cain had an MVP-caliber season in 2018, which more than covered for Domingo Santana’s sudden power outage and helped lead the Brewers within one victory of a World Series berth. Shaw proved to be passable at second base in a small sample. So did Moustakas, whose return (along with Keston Hiura’s emergence) provided depth that saved the team when Shaw’s bat collapsed. Jhoulys Chacin and Wade Miley ended up anchoring the rotation after Stearns was mocked for making them his big pitching acquisitions just months prior.

Some of Stearns’ risks haven’t worked out. Handing the keys to three rookies in the rotation proved to be a disaster, but the additions of Gio Gonzalez and Jordan Lyles helped to correct it. The Jonathan Schoop trade was an absolute flop.

The gamble that Stearns is taking this time around is much greater than any of those, however, and it’s an incredibly fascinating one. He’s betting that he can successfully rebuild a large portion of the team’s 25-man roster in one offseason amid a competitive window. He needs to build an almost entirely new infield and restructure half of his starting rotation. He’s put himself in a position that will require him to be very aggressive on the free agent market to fill the various holes he has created. If he does deal Hader, it must be for a haul that would make the club better immediately.

Stearns has already taken the first step in filling the many holes that he needs to address, reportedly acquiring Omar Narvaez from the Seattle Mariners to serve as Milwaukee’s new starting catcher. Narvaez is one of baseball’s best offensive catchers, and his 120 wRC+ over the past two seasons is a near-perfect match for Grandal’s 121 mark that he posted in 2019. However, Narvaez is one of the worst defensive backstops in the game. While Grandal finished second among all catchers in Baseball Prospectus’ pitch framing stat in 2019 with 19.4 runs, Narvaez finished ninth-worst at -8.2. He was also one of the worst in the game when it came to keeping the ball in front of him, finishing with -4.3 blocking runs. As a result of those defensive shortcomings, the difference between Grandal and Narvaez in 2019 was roughly four wins according to WARP.

This is a perfect example of how daring Stearns has been thus far in the young offseason. The Brewers will be going from one end of the defensive spectrum to another behind the plate. Either the organization believes they can improve Narvaez’s glove, or perhaps they’re planning on revamping their pitching strategy, replacing soft-tossing command specialists like Zach Davies with harder throwers who rely less on called strikes on the edges and weak contact. It’s a surprising change of course for an organization that gave plenty of playing time to the offensively-limited Erik Kratz in 2018 because of his framing skills. They also prioritized signing Grandal last year because of his elite framing, not just for his bat.

This is the most pivotal offseason of Stearns’ tenure in Milwaukee. What he does this winter will define his legacy as General Manager of the Brewers. He’ll either be remembered as the man who slammed the door shut on a window by gutting the team of role players and fan favorites, or he’ll be remembered as the genius who managed to pull off a dramatic reconstruction of the roster to build an even better team and extend that window, all while remaining competitive the entire time and not wasting a year of Yelich’s prime.

There’s a reality in which everything works out masterfully. A massive spending spree could be coming. The Brewers could add premium free agents and make themselves the favorites in the NL Central. It’s pretty safe to assume that they have the financial capability to make big moves, even if they’re a small-market club.

There’s also a reality in which Stearns’ plan backfires horribly. Attanasio isn’t willing to dish out big contracts, the big free agents sign elsewhere, the Brewers end up with a team full of Plan B’s, one year of the Yelich window is wasted, and the team’s outlook for 2021 and beyond is cloudy.

It’s important to remember that Stearns’ stint at the helm has been nothing but a huge success. He turned the team around faster than anyone could have envisioned with a combination of smart buy-low moves, surprising big acquisitions, and daring risks that have paid off. The Brewers have been a contender in each of the past three seasons, including back-to-back postseason berths.

David Stearns didn’t simply wake up one morning and decide to turn the roster on its head. This is part of his plan for the offseason, and like many of his plans, it’s going to take some time before we see how it all comes together. He thinks that he can make the team better for next season, even if it requires a significant restructuring. It’s bolder and more unconventional than any plan he’s ever enacted before, and it must work. Milwaukee’s chance at a ring is in the balance, and so is his reputation. The Brewers have an interesting offseason ahead of them.

Statistics courtesy of Fangraphs and Baseball Prospectus