📌 Join the BPCrew Chapter in your city and meet up with more Yankees fans! 👉 CLICK HERE
TORONTO, CANADA - SEPTEMBER 21: General manager Brian Cashman of the New York Yankees talks on the phone during batting practice before the start of MLB game action against the Toronto Blue Jays on September 21, 2015 at Rogers Centre in Toronto, Ontario, Canada. (Photo by Tom Szczerbowski/Getty Images)

Brian Cashman talks about his biggest regret as Yankees GM

I know Brian Cashman gets a lot of heat from Yankees fans, especially this offseason because the Yankees are LAST in free agent spending. Despite popular opinion, I actually think that is a good move considering the current state of the team.

If you told me when last season ended that the Yankees would enter 2016 with Starlin Castro — a HUGE upgrade at second base — and Aroldis Chapman — the nastiest reliever in baseball — I would have been happy. Why fans are angry they didn’t overspend for David Price or Jason Heyward, I’ll never know.

The point is I think Cashman is a good GM. Is he the best in the league? No. He has infinite resources at his disposal which is a luxury most GM’s don’t have. He has made mistakes (Carl Pavano, for example) but he has also had successes (Didi Gregorius, for example). A lot of scrutiny comes with being the Yankees GM, but Cashman has handled it pretty well despite the fact that his before/after pictures look like the US Presidents’.

In an interview with MLB.com, Cashman revealed that he wishes he could have the Mike Lowell trade from 1999 back. The Yanks received Ed Yarnall, Todd Noel, and Mark Johnson from the Marlins in exchange for Lowell. All three of those guys were good prospects at the time, but all three were busts.

If you think back to 1999, the Yankees were coming off a historic season and Cashman probably wanted to keep the magic going. Mike Lowell was 25 at the time and had only appeared in 8 games with the Yankees. Cashman’s goal was to solidify the team to repeat as champs in ’99, which they did, but in doing so he overlooked the future.

“We had Scott Brosius and we had a lack of pitching depth in the system,” Cashman recalled. “For the right circumstance, we were willing to move Mike Lowell, who was blocked by Brosius. He’d obviously had a lot of success with us and helped us in the ’98, ’99, 2000 World Series pushes, including 2001, where we obviously fell short in Game 7.

There is no doubt that Brosius was great for the Yankees. The ’98 World Series MVP was clutch in his four seasons in pinstripes. Cashman admitted they did not know what they had in Lowell; they knew he could hit but had questions about his defense. I don’t think they ever expected he would go on to make 4 All Star teams and help his team’s win two World Series championships.

It does make you wonder what would have happened if the Yankees kept Lowell or traded him to a different team for a different package. There might have been no Aaron Boone heroics in 2003. There might not have been a need for the Yanks at third base in ’03, thus prompting them to trade for Alex Rodriguez. They may also have won the 2003 World Series because Lowell would not have been on the Marlins (he finished 11th in NL MVP voting that season).

The Red Sox may not have won the championship in 2007 because Lowell, who was voted World Series MVP that season, would not have been traded to them. There are a million what-if scenarios. Would it have worked out in the Yankees’ favor? We will never know, but it is fun to think about.

Yankees fans: tell us what you think is Cashman’s biggest mistake as Yankees GM. Comment below or reply to me on Twitter @Yankees_talk.