Olney: Trade Sonny Gray to Yankees, as time is right for big markets to get their ace

The Chicago Cubs are doing what they can to pursue another championship, including trading for Jose Quintana a couple of weeks ago. But they could never replicate the level of desperation that the organization operated with in the summer of 2016, amassed over 108 consecutive years they had failed to win the title. That urgency drove the Cubs’ front office into a transaction it probably wouldn’t consider under normal circumstances.

On the day the Cubs traded high-end prospect Gleyber Torres to the Yankees for Aroldis Chapman, Chicago was 20 games over .500. They didn’t need Chapman to reach the postseason again; rather, the club’s executives felt the team needed Chapman as a finishing piece to take the World Series. That was the context in which the Cubs operated then, and because they won Game 7 over the Cleveland Indians last year, their context is very different now.

At this time of year, context is everything as teams make decisions about what to do leading up to the trade deadline, and the context should steer three big-market teams in pursuit of the three best starting pitchers in the market.

Why the Los Angeles Dodgers should pay the price for Yu Darvish

The Dodgers stand where the Cubs did a year ago: With the best record in the National League and an enormous lead in the West, they are all but assured of making the postseason again. The Dodgers are third in the NL in runs, they are first in ERA, and they have one of the more efficient defenses. They probably have more talent on their 40-man roster than any other club. The Dodgers are a great team, and they may well be the best team in the regular season.

But making the postseason doesn’t really move the needle for the Dodgers, who have reached the playoffs in each of the past four years; they’ve been beaten twice in the Division Series round, and twice they’ve lost the NL Championship Series. Another early playoff exit will feel like more of the same -- to the team’s fans and to at least some of the players. As a veteran mentioned last year, you get tired of watching the highlights of the 1988 Dodgers on the big screen at Dodger Stadium, from the last time the franchise won the World Series.

Clayton Kershaw's situation adds another layer to the Dodgers’ context. Manager Dave Roberts indicated to reporters that the team believes Kershaw will be back for the final weeks of the regular season, and that may turn out to be the case. But Kershaw has had repeated back ailments in recent years, with a condition that is often regressive for athletes, and nobody can predict with certainty whether he will have a setback swinging a bat, running the bases or preparing; it isn’t in Kershaw’s nature to do anything half-speed.

By paying the high asking price that the Rangers have set on Darvish -- and presumably, it would cost the Dodgers at least one of their best prospects, similar to the Yankees’ asking price for Chapman last season -- the Dodgers would build a needed safety net. Beyond the continued concern over Kershaw’s back, Rich Hill and Brandon McCarthy have had blister problems, and Alex Wood went down with a shoulder problem earlier this year. If the Dodgers traded for Darvish, and Kershaw is healthy in October, the Dodgers would be in position to go toe-to-toe with any other rotation: Kershaw and Darvish, followed by their choice of Wood or Hill or McCarthy or Kenta Maeda, depending on health, depending on who is throwing the best, depending on the matchups.

Last year, the Dodgers made a deadline deal for a couple of rentals, Hill and right fielder Josh Reddick. In six regular-season starts, Hill had a 1.83 ERA. The Dodgers passed on another possible deal for reliever Andrew Miller, who would’ve cost them the two primary prospects the Yankees asked of all teams. On one hand, Miller may well have required a swap of Cody Bellinger, and on the other hand, it’s easy to wonder how the Dodgers would’ve fared in the NL Championship Series against the Cubs if they had been armed with Miller, who helped the Indians reach Game 7 of the World Series.

These are painful decisions, and generally, Dodgers baseball ops president Andrew Friedman is known as a careful manager of assets. Some rival evaluators don’t think he’ll step out of his old comfortable robe of operation and do what it takes to get Darvish.

But he should. Now is the Dodgers’ time. They might have the best team the Dodgers have ever fielded in Los Angeles, and Darvish could make the difference.

The New York Yankees should trade for Sonny Gray

The right-hander’s ugly line against Toronto on Tuesday night obscured the excellence of his work -- the great changeup, the excellent movement on his fastball, the domination of the lowest sliver of the strike zone. He is 27 years old, he’s healthy and he's throwing perhaps the best of his career.

When the Yankees made their big trade last week for Tommy Kahnle, David Robertson and Todd Frazier, the rationale was to acquire pitchers who can help them beyond 2017. This is true for Gray, as well. He would help their chances of making the playoffs this year and of winning in the postseason, as Gray is known as a big-stage performer after his strong October showing against the Tigers as a rookie. And he would also help the Yankees' chances in 2018 and 2019, before he finally reaches free agency.

And there’s no doubt about this: The Yankees need starting pitchers for 2018. Luis Severino will be back, but Michael Pineda was lost to an elbow injury (and would’ve been gone as a free agent, anyway). CC Sabathia’s contract is about to expire, and Masahiro Tanaka could opt out of his deal (and is a major health risk if he stays). Gray would slot in next year and the year after that as the No. 2 or No. 3.

The Yankees are dealing from a greater position of prospect strength than they’ve had in more than two decades, and they should tap into it for the right-hander.

The Chicago Cubs should endeavor to trade for Justin Verlander

It may be that the Cubs and Tigers can’t find middle ground on a Verlander deal, with Detroit insisting on a prospect return as well as financial relief. But he’s a worthwhile target for the Cubs, who might be one of the few teams to which Verlander would approve a trade. Friends say Verlander wants to win now and get back to the World Series, and the Tigers are about to head into a major restructuring.

Verlander is owed about $70 million for the rest of this year and the next two seasons, and the Cubs and Tigers would need to make the money work. If the Cubs can get the Tigers to kick in some big money and turn him into a $20 million-a-year pitcher for them -- rather than $28 million -- then Chicago would have the flexibility to squeeze him in. John Lackey is making $16 million this year and his contract is set to expire. Jake Arrieta is making $15.637 million, in the last season before he heads into free agency. With the addition of Verlander, the Cubs’ rotation could look like this for 2018:

1. Jon Lester

2. Verlander

3. Quintana

4. Kyle Hendricks

5. Mike Montgomery

It’s possible that, if the Cubs take on a lot of Verlander’s salary in the next week, they could also have a shot at landing coveted reliever Justin Wilson. Rival evaluators say the Tigers are trying to attach some of their more attractive assets to some of the higher-salaried players they are working to move.

Gray better fits the Cubs’ budget, of course, but he would cost a big-time package of prospects, and after trading high-end for Chapman and Quintana, Theo Epstein might prefer to take on a salary rather than dip into the best of his minor league pool.