Henning: How the Justin Upton deal was made

Lynn Henning
The Detroit News

Hints first were dropped around Christmas.

Tigers owner Mike Ilitch, always focused on his roster, always mindful of soft spots and how they might be made pluses, wondered about left field.

Were the Tigers going to contend in 2016 with a Cameron Maybin-Tyler Collins arrangement at a position where offense is a mandate?

The Tigers front office could always swallow hard at such moments and make a plausible case: Maybin was only 29. He had not peaked, in their minds, and with the incentive of a $9 million (or $1 million buyout) option for 2017, there was a reasonable chance he could be a right-handed hitting surprise in 2016.

Collins, too, could crack a home run and score a man from first base with a left-handed bat that has its crunch.

Ilitch wasn’t convinced.

Outside help

Once the Tigers returned from their Christmas week office shutdown, Ilitch had gone from uneasy to committed: He wanted one of those free-agent outfielders who was still on the market: Alex Gordon (until he re-signed with the Royals), Yoenis Cespedes, or Justin Upton.

The Tigers went to work. Scouts and analytics staffers huddled. Alan Trammell, an assistant to general manager Al Avila, and Tigers broadcaster Kirk Gibson, were grilled about Upton from their days in Arizona when all worked for the Diamondbacks.

The Tigers liked Cespedes immensely. His power. His arm in left field.

But they kept looking at age, and internal projections, and everything from on-base percentage to intangibles, and they reported to their owner that Detroit’s best option was Upton.

They were still serious about Cespedes even into last week. But five days ago, on Friday, Avila and manager Brad Ausmus flew to Scottsdale, Ariz., to begin — in concert with chief negotiator John Westhoff — a bid to sign a 28-year-old left fielder who might be the best answer to Ilitch’s hopes and dreams.

And, in fact, theirs.

Three days later Upton was destined for Detroit as part of a six-year, $132-million contract that is scheduled to be announced formally Wednesday, once Upton’s physical exam has proved assuring. Upton is expected to appear, probably alongside Ilitch and Avila, at a Comerica Park press briefing.

Ilitch always has taken a quasi-GM’s view of his roster. He is baseball savvy and understands strengths and weaknesses in step with the most studious of fans and Tigers intimates.

He also knew his payroll was about to crack open. Spilling from it, if he intended to sign one of the hotshots, would be another $100-million-plus check that would trigger a few million in luxury-tax fines.

But this is Ilitch. He likes his baseball team. He wants a championship. And he, in step with so many others, didn’t see the Tigers validly contending with a potential hole in left.

The Tigers did not fudge about the seeming Upton-Cespedes jump ball when Ilitch asked for their recommendation. They would have been happy with Cespedes. But they believed Upton would be the better investment, in the short and long terms.

They will say as much at Wednesday’s press conference, all because it was a conviction forged by those conversations with scouts, by those debriefings of Gibson and Trammell, and by work their wider, broader analytics team had done in crunching algorithms and inside-baseball numbers.

Davis left out

It was not only a matter of Cespedes or Upton. The Tigers, in fact, had considered another sexy free agent, left-handed power hitter Chris Davis.

But there were realities to Davis that didn’t quite mesh with Detroit’s deepest needs.

He is a first baseman. And while he has played left field, and while his agent Scott Boras believes with Boras-grade certainty that he could be an All-Star left fielder, Davis wasn’t going to find great comfort or harmony — in the Tigers’ view — in Comerica Park’s left-field territories.

And so it came down to a decision between two exceedingly talented players.

Cespedes, who turned 30 in October, wanted a lot of years and a lot of money.

Upton, 28, was hunting for something similar during his first bout with free agency.

A key difference, beyond the Tigers’ internal conclusions, became a two-year opt-out. Upton, at age 30, can regain free agency if he views it in his interests to again try the market. Given the rate at which baseball salaries have moved, he could find greater riches in two years with another club.

The Tigers, meanwhile, could be freed of a big contract at a point they likely will be interested in shedding payroll and aging players, especially if left-handed hitting prospect Christin Stewart continues to evolve as a team anticipates.

Ilitch was informed continually last weekend as the Tigers-Upton conversations came closer to resolution.

By the end of the day Monday, a team from Detroit had its new left fielder. And an owner who continues to amaze once again had his man.