Inside the art of MLB dealing

With Monday’s trade deadline looming, the Star spoke with former GMs on the process

The clock is ticking a little louder than usual for Major League Baseball’s 30 general managers, who in these final hours before Monday’s 4 p.m. non-waiver trade deadline are furiously working the phones in a last-ditch effort to improve their clubs for either the short or long term.

Operating on even less sleep than usual and fuelled by caffeine and adrenaline, they will make decisions that will influence post-season races and even the World Series. Some will make moves they will later regret, perhaps setting their organization back several years.

“It’s a nerve-wracking time, but a very exciting time,” says Jim Beattie, former GM of the Montreal Expos and Baltimore Orioles.

“The channeling of your emotions becomes crucial to your success or lack thereof in your decision-making process,” adds Dan O’Dowd, who helmed the Colorado Rockies for15 years before joining MLB Network last season.

With the deadline looming, the Star spoke with four former major-league GMs about the process of making trades and the art of the deal. Combined, they have more than a century of baseball experience and shared the lessons they learned from dozens of deadline deals. Lesson 1: Be prepared.

The trade deadline is not an exam for which you can cram. If you’re scrambling to study a potential trade partner’s farm system in the midst of negotiating a trade, you are bound to fail.

“You’re creating prep lists and understanding the 29 other clubs’ strengths in the minor-league system and needs at the major-league level all year long, not just at the trade deadline,” O’Dowd said. “You know going into a trade deadline where your potential matches are.”

Now, more than ever before, there’s no excuse not to know everything about the other side, given all the analytical information available to every team.

“There was a time in this game when you only knew what you thought you knew and you didn’t have the resources that we have today,” said Dan Evans, who was GM of the Los Angeles Dodgers from 2001 to 2004 and now works as a scout for the Blue Jays. “We’re almost operating in a CSI environment now. We’re just trying to distinguish which information is really important to the deal and which is cluttering it.”

Lesson 2: Be persistent.

Facts change fast this time of year and you should take nothing for granted.

“A ‘No’ on Monday doesn’t mean a ‘No’ on Tuesday,” said Gord Ash, who was Blue Jays GM from 1995 to 2001 before joining the Milwaukee Brewers’ front office. “No never means no until the deadline.”

This was one of Alex Anthopoulos’ great strengths. The former Jays GM reportedly wore down Billy Beane, his Oakland counterpart, in order to pry away Josh Donaldson, and had been asking about Troy Tulowitzki’s availability for months prior to last year’s deadline-week deal.

“He’s like a dog with a bone,” says Beattie, who, like Evans, now works as a scout with the Jays. “You gotta stay on the phone because things change day to day, hour to hour.”

MIAMI— The Miami Marlins acquired the pitching reinforcements they sought in a trade that cost them four players, including two minorleaguers.

Right-handers Andrew Cashner and Colin Rea were sent to Miami by the San Diego Padres in a seven-player deal, two people familiar with the deal said.

The Marlins, eager to shore up their rotation for a playoff push, will also receive pitching prospect Tayron Guerrero for right-handers Jarred Cosart and Carter Capps and two minor leaguers, pitching prospect Luis Castillo and first baseman Josh Naylor.

In the weeks leading up to last year’s deadline, for instance, the Detroit Tigers told teams they weren’t interested in trading David Price. Forty-eight hours before the deadline, they changed their minds. Lesson 3: Don’t try to win every trade.

This was a lesson that came up repeatedly, and while it may seem counterintuitive at first glance, maintaining relationships is a key part of being a successful GM. If you enter into negotiations intent on beating the other guy, you’ll never find the common ground necessary to get a deal done.

“You’ve got to recognize what the other party is trying to accomplish,” Evans said. “Their motivation is absolutely part of the equation and if you take them into consideration throughout your discussion I think it’s easier to get the deal done.”

Cashner is 4-7 this year with a 4.76 ERA in 16 starts, and has a career record of 30-49 with a 3.73 ERA in seven seasons. Rea, who is in his second major league season, is 5-5 with a 4.98 ERA in 19 games this season.

Cashner has a $7.15 million contract and becomes a free agent after this season. Rea, 26, has a salary of $510,200 and is under team control through 2018.

The prize in the deal for the Padres might be Naylor, 19, a left-handed power hitter taken by the Marlins in the first round of the 2015 draft.

The Mississauga, Ont., native is batting .269 with nine home runs this year for Single-A Greensboro.

Cosart went 13-11 in 2014 with Hous-

“There’s battles and there’s wars,” O’Dowd said. “Ultimately you’re trying to win the war and to do that you have to win as many battles as possible. But if you win battles at the expense of your integrity and character, you’re sure to lose the war.” Lesson 4: Trust no one.

Building trust with other GMs may be integral to good working relationships, but you should never expect the other side to work for you.

“It could be your brother on the other end of that phone and he’s going to do what’s best for him to win,” O’Dowd said. “If you don’t ask the right questions and you don’t do the due diligence on the players you’re discussing, that’s on you. You learn eventually that there has to be a level of character, integrity and honesty with everything you do — but don’t expect that from anybody else.” ton and Miami but has struggled since. This year he’s 0-1 with a 5.95 ERA in four starts with the Marlins, and 3-4 with a 4.09 ERA in 10 starts for Triple-A New Orleans.

Capps, a hard-throwing reliever, underwent Tommy John surgery in March and is expected to be ready for opening day 2017.

The Marlins are in contention for their first playoff berth since 2003 despite a shaky rotation. Aside from ace Jose Fernandez, their starters are 23-24 with an ERA of 4.40.

Miami’s rotation was further depleted last week when left-hander Wei-yin Chen went on the disabled list because of a sprained elbow. Cashner and Rea will join Fernandez, Tom Koehler and Adam Conley. Lesson 5: Ignore the human element at your peril.

Deals can fall apart for petty reasons, like pride and hurt feelings, so you have to respect your trade partner. By the same token, persistent rumours can affect clubhouse camaraderie and hurt a player’s performance. The other human element to consider is the player you’re acquiring.

“Ultimately when you’re dealing with people that breathe and have a heartbeat, you have no idea how they’re going to react to a different culture, environment and situation, especially within a short window of two months,” O’Dowd said, adding he always thought of trades in two parts: making the trade and making the trade work. “Not only do you want to know what kind of player you’re getting, you want to know ev- erything about the person you’re getting so you can put that person into the best possible situation from a teaching and coaching and environmental standpoint for him to maximize his skill set.”

That could mean helping his family find a place to live or encouraging players to reach out to the new guy to make him feel welcome or even making sure the player knows how to get to the ballpark.

Expectations are also sometimes greater on players traded mid-season.

“It’s different from being on an opening-day roster when you’re just expected to contribute like you’re supposed to contribute,” Evans said. “Suddenly you’re supposed to be the answer. It takes a special guy with some special character and makeup to be able to handle that and that’s something you have to take into consideration. Has the guy you’re acquiring ever been in this situation before? How did he perform?” Lesson 6: Sometimes the best deals are the ones you don’t make.

“It’s called the trade deadline, not the must-trade deadline,” O’Dowd said, adding that the pressure to get something — anything — done at this time of year can lead to lots of bad decisions. One impulsive move could derail an organization for several years.

“If you’re uncomfortable and anxious through the process, I learned you shouldn’t do it, no matter what.”

Ash, who famously traded away a 23-year-old Michael Young to the Texas Rangers in an ill-fated trade for Esteban Loaiza but also acquired Jose Cruz for a relative pittance in another deadline deal, said he got lots of calls inquiring about a young right-hander named Roy Halladay, who struggled early in his career.

“I’m glad I resisted those.”