What was the best trade you saw made?

The Clemens-for-Wells deal in 1999 was by far the biggest trade I was a part of, but getting David Justice for Ricky Ledee, Zach Day and Jake Westbrook at the time helped the Yankees get to and win the 2000 World Series. The team was in dire need of an outfielder and they were interested in Sammy Sosa, Preston Wilson, Larry Walker and Jim Edmonds. A random call to Cleveland told us that Justice might be available, and even though he was not on our radar, the idea was interesting enough to engage some trade talks. Justice ended up playing a solid OF and hitting some clutch HR’s. Ledee has bounced around as a fourth outfielder, Day is a decent 5^th starter and Westbrook has developed into a pretty good starter for the Indians, but they would not have gotten the Yankees to the Series. Great pick-up.

And the worst?

Gee there were so many, like Denny Neagle and Raul Mondesi, but getting Jeff Weaver in 2002 was our worst. He was making a lot of money in Detroit and they needed to get rid of him. He was young and had great movement on his fastball. But his Southern Cal attitude did not mesh well and he never fit in. His inconsistency drove everyone nuts and by 2003 he was in the doghouse even before giving up the Series turning homerun against the Marlins. We gave up a few prospects and one of our starters – Ted Lilly — for him. Lilly had a good season and then went on to Oakland and Toronto where he has settled in as a nice number 3 or 4 starter.

What was the atmosphere like around Steinbrenner?

When he was in town, everyone walked on eggshells or avoided making eye contact. The few people he did speak to were always nervous and he liked it that way. I had a few run-ins with him - getting yelled at and threatened - but after a while you enjoy it. I would have trouble holding in my laughter at some of the lines he used. Funny guy, but not the person you want to work for. I know fans love him because he’ll do anything to win, but at times he is a heartless dictator who thrives on fear. If anyone ever recorded his tirades, it would shock people. To his credit he does put a lot of money into his team and treats his players right. But if I had him alone in a dark alley………

Which player’s departure (via free agency or trade) was the biggest loss?

Definitely has to be Andy Pettitte. For some reason, the team did not think he wanted to come back, and they were probably right, but they should have made a nice offer early on and he might have stayed. Yankees best Lefty since Guidry.

Are there any players that the Yanks wanted to get but weren’t able to acquire? Who did they get instead?

Well, Steinbrenner always want the new “it” guy, He tried for Clemens several times before finally getting him. He wanted Juan Gonzalez a few times but was thankfully talked out of it. The Yankees usually got whomever they really wanted but some players were just unavailable like a Todd Helton from Colorado. There was a lot of talk but the Rockies wanted Soriano and several other players., which was too steep at the time. After 2000, we were planning on making one big free agent signing and the top two choices were Mussina or Manny. We wanted Manny because he was from NYC and he was the best RBI guy I ever saw. But after many discussions, we all agreed that pitching was top priority. Funny, even though Moose has pitched well, the team has yet to win the Series [with him], but Manny won in 2004.