Dallas Keuchel and Craig Kimbrel will soon sign free agent deals. Where will they land?

Two of the best pitchers in baseball have been without a job for months.

Craig Kimbrel Boston Red Sox
Craig Kimbrel remains a free agent at the end of May. Barry Chin / The Boston Globe

It was never supposed to take this long.

But as the markets for Keuchel and Kimbrel, both 31 years of age, stagnated through the winter months, and then the spring – with neither player willing to sign for below their asking prices, and teams having to weigh the cost of both the player and the draft pick and slot money they would have to give up – the date June 2, the day before the 2019 MLB draft and the date the draft-pick penalties expire, loomed ever larger.

It is doubtful either of these highly decorated pitchers would have chosen this path – remaining unsigned some two months into the 2019 season – at the outset of free agency. But at a certain point, the nearer we got to June 2, it became a useful, winning strategy: Allow the pressures of a developing pennant race and the natural attrition of pitchers (through injury and underperformance) to create a frenzied atmosphere, in which almost every contending team can now say they need either Keuchel or Kimbrel, or both.

It is possible handshake agreements already exist between one or both pitchers and one or two teams, which would be announced after midnight, when the draft-pick penalty expires. It is also possible one or two bold teams could undercut the market, ahead of the midnight cutoff, by signing one of the pitchers and viewing the draft-pick penalty as the cost of snatching him out from under the others.

But assuming neither is true, and the stroke of midnight brings the expected bidding frenzy and an eventual resolution to this bizarre saga, here are three questions that still need to be answered:

1. Which team(s) will win the Keuchel and Kimbrel sweepstakes?

Keuchel, the 2015 American League Cy Young winner and a workhorse who has averaged 200 innings (regular and postseason combined) the past five seasons, could benefit from a bidding war of sorts between the rival New York Yankees and Tampa Bay Rays, who are currently jockeying for the AL East lead.

We say “of sorts” because the Yankees have one of the game’s largest payrolls, and the Rays one of its smallest – which would give the Yankees a massive advantage. But there are also indications Keuchel might accept a hefty one-year deal, then try his luck at free agency again this winter, in which case the Rays – who are currently making do with a rotation of Blake Snell, Charlie Morton and “openers” on the other days – might stand a chance.

This much remains true: a motivated Yankees team – which entered the weekend with four starters (Luis Severino, CC Sabathia, Jonathan Loaisiga and Jordan Montgomery) on the injured list – would be difficult to outbid under any scenario.

Other contenders in need of a front-line starting pitcher include the Milwaukee Brewers, Minnesota Twins and Philadelphia Phillies. But the industry consensus is that Keuchel winds up in the Bronx.

With Kimbrel, the best closer of his generation, the market should be no less vibrant, with nearly every contender in need of another back-end-of-the-bullpen arm. That includes blue-bloods such as the Chicago Cubs, Los Angeles Dodgers and Boston Red Sox (and wouldn’t it be something if Kimbrel winds up back in Boston, where he won a World Series ring in 2018?), as well as the Atlanta Braves and San Diego Padres (both of whose uniforms Kimbrel has worn in the past).

The guess here is that Kimbrel winds up in Atlanta, where the defending NL East-champion Braves, after some modest offseason spending, entered the weekend three games behind the division-leading Phillies following a two-game sweep at the hands of the Washington Nationals.

2. How soon will they be ready to pitch?

Both Keuchel and Kimbrel reportedly have been keeping to regular throwing schedules that mimic their typical regular-season schedules, with Keuchel throwing simulated games of around 100 pitches every five days to build up his arm strength and Kimbrel throwing more frequently in shorter stints. At least one of Keuchel’s simulated games was open to major league scouts, and the Yankees were among the teams reportedly present.

Keuchel’s agent, Scott Boras, told this week his client would only need a week in the minor leagues to get himself ready for big league games. That sounds a bit optimistic, as a one-week assignment would allow for only two starts. Tack on a third minor-league start, and you would be looking at two weeks and change before Keuchel would be ready to start in the big leagues. That sounds more realistic.

Kimbrel, it stands to reason, would require a similar time frame – say, five to seven minor-league relief appearances over a two- to three-week period – to get himself into regular-season shape.

The good news for the contenders that acquire Keuchel and Kimbrel: their 2019 odometers will be starting from zero somewhere around mid-June, meaning their arms should still be relatively fresh when October rolls around.

3. Is this situation a problem for baseball?

The short answer: yes.

The qualifying offer/draft-pick compensation system – where teams can extend a one-year qualifying offer ($17.9 million in 2018) to a pending free agent, and receive a draft pick as compensation if the offer is rejected and the player signs elsewhere – was well-intended, with the goal of leveling the playing field by compensating small-market teams who lose their best players to free agency and penalizing large-market teams that swallow up the best free agents year after year.

But as the game has skewed younger, the value of draft picks and slot money has soared, and it is the players who have suffered as a result. While Keuchel and Kimbrel are extreme examples, other players have been affected by the rules in years past – most notably third baseman Mike Moustakas, who, after the 2017 season, rejected the Kansas City Royals’ qualifying offer, found no takers on the free agent market and wound up signing back with the Royals the following March on a one-year deal for less than half the qualifying offer’s value.

Clearly, the system needs to be tweaked, if not done away with completely – and this will almost certainly be a topic of discussion in the next round of talks between union and league negotiators. Injuries already do enough to rob the game of some its best players (where have you gone, Aaron Judge?) without a broken economic system sidelining perfectly healthy stars for almost half a season.