The life of an MLB GM at the trade deadline: What it takes to close a deal

I was a general manager for 16 years for the Reds and Nationals and had my share of “buying,” “selling” and even “standing pat.” Every day a GM is on the job, they are preparing for trades – whether those deals ultimately occur today, tomorrow, next month, next year or even in the next decade. You can never do enough homework. You can never have enough information on players. The more information you have, the better your chances of making good trades.

The week leading up to the MLB trade deadline is a hectic time for GMs and their staff. You are inundated with texts and phone calls. You are constantly communicating with other GMs and brainstorming possible deals with your executive cabinet. Most teams are working on four to five trades at a time.

There is no sleep, there is no rest for the mind, the clock is ticking, and if you can’t close deals to improve your organization, you have failed at your job. At the deadline, the GM is just as important to a club as the star player.

My favorite trade deadline was with the Reds in 1995, when we swept the Dodgers in the Division Series before bowing out to the Braves in the NLCS. We acquired three starting pitchers and a Gold Glove outfielder in two trades that were made 10 days apart. The first deal was an eight-player trade with the Giants that landed starters Mark Portugal and David Burba and center fielder Darren Lewis. The second deal sent left-hander CJ Nitkowski and a player to be named to the Tigers for lefty David Wells. Those trades propelled the Reds to a first-place finish in the NL Central, winning the division over the Astros by nine games.

I think 1998 was my best year of selling at the trade deadline. Reds ownership told me to lower payroll during a disappointing season. I traded Jeff Shaw, the Rolaids Relief Man Award winner the previous year, for first baseman Paul Konerko and lefty Dennys Reyes. The Reds finished 77-85 in ’98 but won 96 games the following year. I traded Konerko for Mike Cameron in November 1998. In 2000, I then traded Cameron as part of a package for future Hall of Famer Ken Griffey Jr.

None of those trades would have happened if the Reds weren’t ready to be sellers at the deadline in ’98. It’s a great reminder: An organization’s planning for trades begins long before late July.

Baseball is always changing, and the GM role has evolved considerably since I last held the title. But some things haven’t changed. Here is what trade season is like if you’re sitting in the GM’s chair.


Reds GM Jim Bowden, left, talks with manager Bob Boone in 2002. (Larry Goren / Four Seam Images / Associated Press)

Managing up to ownership

It’s the owner’s team and the GM works for them, just like the relationship between a player and his agent. Some owners are more hands on than others. In any case, it’s imperative for the GM and owner to be on the same page. A collaborative approach is the best way to do business.

However, sometimes it’s more difficult to get a deal done with ownership than with an opposing GM. For example, when I was GM of the Reds in the mid-90s, I once reached an agreement on a trade involving first baseman Hal Morris, pending owner approval. Then-owner Marge Schott nixed the deal because of her relationship di lei with Morris’ wife at the time, Megan. I explained to Schott that I wasn’t trading Megan and they could remain friends, but after two days of trying to convince her, I had to accept that I wasn’t allowed to make the deal.

Then there was a near deal for Phillies third baseman Scott Rolen in 2002 that would have sent the Reds’ 1997 first-round pick, Brandon Larson, to Philadelphia. That deal was nixed by Reds president John Allen for financial reasons. I then tried to sell prospects from A-ball to raise the necessary funds, but even after I made up the financial difference, I still couldn’t get approval. On the flip side, in 1995 when I acquired Wells from the Tigers, we were way over budget, but after two days of persuasion, Schott gave me approval to make that key deal.

Doing deals isn’t just about negotiating with the other team. Sometimes, convincing your own house is the most difficult part of closing a trade.

Be prepared

Preparation begins with self-scouting your own players. GMs must ensure the organization has evaluated its players at all levels in a fair and unbiased fashion. Too often, organizations “over-evaluate” their players, which makes it more difficult for those teams to complete trades. Knowing what you have and valuing the players properly are imperative in this industry. In this respect, knowing your 17-year-old pitcher in A-ball is just as important as knowing the All-Star veteran on your major-league roster.

For example, as GM of the Reds, I acquired right-handed pitcher Juan Guzmán in a trade with the Orioles for lefty reliever BJ Ryan and 17-year-old righty Jacobo Sequea on July 31, 1999. Guzmán would go 6-3 with a 3.03 ERA in 12 starts for Cincinnati and helped the Reds finish with 96 wins that year.

Ryan went on to have a solid career with the Orioles and Blue Jays, but at the time, the trade was held up over Sequea, a player the Orioles wanted badly. We knew our players well and didn’t think he was a prospect. And as it turned out, Sequea never pitched in the big leagues.

Another example of the importance of self-scouting was when I traded outfielder Roberto Kelly to the Braves for Deion Sanders in May 1994. The Braves wouldn’t make the trade unless the Reds included a Low-A or Rookie-ball pitcher. We swapped names for hours before they asked for Roger Etheridge, a hard-throwing lefty who was having a banner year by the numbers. Our top evaluators and I had spent a lot of time watching Etheridge, and thought he lacked deception and command. We quickly put him in the deal because we didn’t think he would make it to the big leagues. He never did.

Another crucial part of preparation is evaluating the other 29 teams’ players. This includes knowing about the players’ physical tools, intelligence, makeup, character, performance and present production, along with projecting their future production.

When I was with the Reds in 1997, we made sure right-handed minor-league reliever Danny Graves was included in the John Smiley trade with Cleveland based on the recommendation of one of our top evaluators, Jack McKeon. A lot of the scouting reports on Graves weren’t glowing, and mentioned an average fastball with sink. However, McKeon loved his competitiveness, intangibles and that he wasn’t afraid to pitch inside and go right at hitters. Graves ended up with 182 career saves and made two All-Star teams. He had a 5.54 ERA and below-average scouting grades when we traded for him. Great scouting by McKeon made that trade for the Reds.

Finally, work must be done to find trade fits. Trades need to work for both teams, so understanding the needs and wants of other organizations is imperative. I used to have a white board with trade deadline targets in my office. It listed all the other teams and the players we’d targeted in their organizations, from major-leaguers to Rookie-ball guys. I also listed all of the players from our organization that opposing teams had shown interest in. This helped highlight the teams we could match up best with on deals.

Relationships matter

GMs can make trades with only 29 other teams so it’s important to build a professional and personal relationship with every one of your front-office counterparts. These are the people you must do business with to improve your organization outside of free agency, waivers or the drafts.

Each GM has their own style of negotiating. Some like constant communication, others prefer occasional check-ins. Some ask for a lot and take their time in lowering demands; others are straightforward and tell you exactly what they will and won’t do in a deal. Understanding the individual style and process of all the other GMs is vital.

For example, Dave Dombrowski of the Phillies and Brian Cashman of the Yankees are “straight shooters” who get right to the point. They are transparent and say what they want to do or what they are willing to do. When a deal is close, they know how to close it and often do because of their direct style of communication.

Theo Epstein, formerly of the Red Sox and Cubs, and I made the first trade done strictly by emails, and he and I were comfortable communicating in various ways. By contrast, Walt Jocketty of the Cardinals, for example, preferred personal phone conversations, even after texts and emails were commonplace.

It doesn’t matter the method. As a GM, you just want to make sure you know your counterparts’ preference and adjust accordingly to give yourself the best chance to close a deal.

It takes an entire organization

Many departments in an organization contribute throughout the trade process. Seamless coordination and communication are essential.

Player development must answer key questions when acquiring prospects: Can we improve the players we are trading for? This could include a swing change, an adjustment in a delivery or simply a new approach. Also, at which level should we assign them? Then there’s the analytics department, whose insights can support or present counterarguments to the scouting department’s recommendations.

The research, development, science and technology department uses science and new technologies to further improve the evaluation processes and gain a competitive edge. For example, R&D groups, working in concert with the analytics department, have recently helped teams change pitchers ‘repertoires and pitch usages, leading to improved performance and increasing the pitchers’ value. When an organization considers trading for a pitcher, R&D might recommend the acquisition and propose something like this: If we increase his breaking ball usage by 20 percent and correspondingly decrease his fastball usage, his ERA could be lowered from 3.92 to 2.87. Or if the pitcher can change his hip turn or lengthen his front leg plant, we can add 3 to 4 mph to his fastball. For a hitter, they might recommend moving his hands up at the start of his swing or rotating his hands by a certain amount to improve bat speed and contact, which could lead to better results.

The team’s accounting department is crucial in providing accurate projected payroll figures for the next four to five years. GMs must have a long-term outlook in roster construction so they know, years in advance, when they’ll be able to add payroll or need to reduce it.

Other departments are actively involved before a deal is finalized, from the medical group doing due diligence on acquired players and cooperating with the opposing team’s medical requests on departing players, to legal performing analysis and reviewing the contracts of new players, to media relations having a plan in place to announce a trade and promote it across platforms.

Once a trade is made, you need to inform the departing player in person and talk with the arriving player by phone. This should be done by the GM and manager. Also the traveling secretary must be on-call to immediately arrange transportation, housing and meal allowances for the players involved in coordination with the other team’s traveling secretary.

Relentless persistence can pay off

As a GM, if you really want a player, communicating nonstop about it and never giving up, no matter how many times the other team says “no,” can actually work in the long term. When I traded for Griffey, it took more than seven years to strike a deal between the Reds and Mariners. I was relentless. I was told “no” more than 100 times by then-Seattle GM Woody Woodward, who told me it would have to be the next GM who traded Griffey.

In fact, it was, because the deal was done on Feb. 10, 2000, with Hall of Fame executive Pat Gillick, who himself had told me “no” more than 20 times before we eventually made that blockbuster trade.

(Top photo of Brian Cashman: Michael Reaves / Getty Images)

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