Should the Yankees go all-in right now?

The Yankees have had a very successful offseason already. The team handled their biggest need and want heading into next year, agreeing to a nine-year, $324 million contract with Gerrit Cole to be their next ace. The team also returned veteran outfielder Brett Gardner on a one-year deal to fill a gap in the outfield with Aaron Hicks out for likely the first half of the season.

There are few, if any, holes left on the roster, but that doesn’t mean the team is relaxing on pursuing talent. They’ve remained active on the market, most notably checking in on the availability of Brewers reliever Josh Hader. Hader is an extremely talented pitcher, and has been one of, if not the best reliever in baseball over the past two years. His performance in 2018 was so dominant that he received down-ballot votes for the Cy Young Award, and his 281 strikeouts in 157 innings over the past two seasons are truly elite.

Hader would unquestionably be an asset to the Yankees if they acquired him, and subsequently, the Brewers would be justified in asking for a high price to move him. Not only is Hader a top reliever, but he has years of control left in arbitration before he would hit the free agent market. The demand in return for Hader would have to include top prospects, and pieces that are close to the majors if Milwaukee wants to flip him and stay competitive.

The question, then, pertains to whether this a good use of the resources the Yankees have in front of them. Should the Yankees go all-in and pursue Hader? Should they be aggressive with a different option? Or would it be best to not make a move at all?

In terms of competition for improving the bullpen, the only other name out there that should really interest the Yankees is Dellin Betances. The Yankees are more than familiar with Betances, and despite his occasional blow-ups, Betances was an elite flamethrower in the back of the Yankee pen. The concern over his injuries in 2019 is a valid one to consider, and to what degree you believe they will impact his future affects whether you bother negotiating with him. So far, the Yankees have been distant, which signals that they would rather not take the risk even on a likely one-year deal.

If Betances is out of the running, then Hader becomes the focal point of the discussion. The Brewers could reasonably demand a top pitching prospect like Deivi Garcia, a major-league ready bat like Miguel Andujar, and probably still seek other lower-level pieces. That’s a lot of the Yankees’ bargaining chips spent on one deal for a piece that augments what’s already a team strength. There’s a lot of risk that the Yankees have to consider when acquiring a reliever, even an excellent one like Hader, before the season even begins.

On one hand, this is possibly the best time to negotiate if the Yankees are dead-set on improving the pen. The Yankees are among only a few teams with the means and the desire to trade for Hader at the moment, and while it will still be costly, the deal likely only becomes more expensive if it is negotiated at the trade deadline. The concentration of multiple teams that will know by that point that they’re in contention, mixed with the scarcity of quality relievers, could have the price skyrocketing. That’s the sort of scenario that benefited the Yankees when they dealt Aroldis Chapman and Andrew Miller back in 2016, and that intensity is rarely present when negotiating over the offseason, with so many teams unsure of where they stand.

However, making this move now before play begins limits the Yankees ability to make moves in the future. Injuries hit at a historic level for New York last season, and while the expectation is that health will improve, no team goes through the year without setbacks. The depth that the Yankees had waiting in the wings saved their season, and a move of this magnitude would remove a huge chunk of it before the first ball is put in play. If a key player goes down for a significant length of time, or possibly the season, the middle of the Yankees’ prospect pool isn’t going to be enough to get an impact player to replace them.

The players that the Yankees would likely have to give up aren’t being valued at their highest points, either. Garcia struggled with the major-league ball when he got called up to Triple-A Scranton last season, posting a 5.40 ERA and allowing eight home runs in 40 innings of work. Andujar struggled to make any contact in the short period he remained off the IL before his season ended with shoulder surgery, and the time off hasn’t helped his defense improve as much as it would’ve being in major-league games. Because of this, it would likely take a lot more to get near the value that Milwaukee would want before pulling the trigger on a trade.

Considering all of this, it may not be wise for the Yankees to go all-in at this point. They’ve got the pieces they wanted, and they’ve put themselves in a great position to lead the pack of contenders into 2020. They can enter the season as perhaps baseball’s best team, with ample depth at their disposal, depth they can still flip to make aggressive moves once the season starts and they have more information at their fingertips.