Could Brian Cashman have acquired Alex Bregman or equivalent?

Supposedly the dynamic is that a team can only get a high pick in the annual June amateur draft by having a very bad record the previous season. Since the Yankees have not had a losing record since 1992, they never have a very high draft pick.

The rules prohibit a team from trading up as often happens in the National Football League (NFL). So, the conventional wisdom goes, a championship caliber team is perpetually stuck drafting at the bottom, late in the first round.

Let's examine a real case. The 2015 draft.

Alex Bregman
Born: March 30, 1994 in Albuquerque, NM (Age 22 and 298 days)
Drafted by the Houston Astros in the 1st round (2nd pick) of the 2015 amateur draft.
Signed June 25, 2015.
Debut: July 25, 2016 (Age 22 and 117 days)

Andrew Benintendi
Born: July 6, 1994 in Cincinnati, OH (Age 22 and 200 days)
Drafted by the Boston Red Sox in the 1st round (7th pick) of the 2015 amateur draft.
Signed June 30, 2015.
Debut: August 2, 2016 (Age 22 and 27 days)

James Kaprielian, pitcher
Born: March 2, 1994 in Laguna Hills, California, United States (Age 22 and 326 days)
Drafted by the New York Yankees in the 1st round (16th) of the 2015 MLB June Amateur Draft.

2016:
Bregman with Astros: 217 PA, 115 OPS+
Benintendi with Red Sox: 118 PA, 117 OPS+
Kaprielian with Tampa, Florida State League A+ ball: 18 innings pitched; 11 innings pitched in 2015 in leagues even lower.

Yankee general manager drafted a pitcher with arm problems.

But Cashman could have traded for either Bregman or Benintendi after their one year obligation with their original teams, assuming that Cashman realized their worth by that time. Here's what Cashman did around the time they first played in the major league: he traded two of his three relief aces.

Aroldis Chapman

• July 25, 2016: Traded by the New York Yankees to the Chicago Cubs for Rashad Crawford (minors), Billy McKinney (minors), Gleyber Torres (minors) and Adam Warren.
• November 3, 2016: Granted Free Agency.
• December 15, 2016: Signed as a Free Agent with the New York Yankees.

The key player acquired by Cashman for Chapman was shortstop Torres, currently rated the top Yankee prospect even though Torres has yet to play above A+ ball. Bregman debuted the day that Chapman was traded.

Andrew Miller

• December 5, 2014: Signed as a Free Agent with the New York Yankees.
• July 31, 2016: Traded by the New York Yankees to the Cleveland Indians for J.P. Feyereisen (minors), Clint Frazier (minors), Justus Sheffield (minors) and Ben Heller.

The key player acquired by Cashman for Miller was outfielder Frazier, who had just been promoted to AAA by Cleveland even though Frazier had been drafted number 5 three years before in 2013. 2016 at AAA: 129 PA, .657 OPS. Benintendi made his debut three days after Miller was traded.

So could Cashman have flipped Torres and Frazier for Gregman or Benintendi? What if Cashman threw in more of the minor league players just acquired for Chapman and Miller? Would that have been enough? If not, then what was the point in trading for them? To have managing partner Hal Steinbrenner, along with much of the media and far too many Yankee fans, think that Cashman was doing a good job? Of what, improving the minor league teams of the Yankees? The objective is for the Yankees to win championships, preferably with star players worth paying to see.