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Former Cubs GM Jim Hendry is his own toughest critic

7-12-2007--Cubs workout Wrigley Field---Cubs GM Jim Hendry----Sun-Times phoby Tom Cruze

7-12-2007--Cubs workout at Wrigley Field---Cubs GM Jim Hendry----Sun-Times photo by Tom Cruze

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How the Cubs did during Jim Hendry’s tenure as GM after he took over on July 5, 2002.

Playoff history: 2003 — Won NLDS over Braves 3-2, lost NLCS to Marlins 4-3. 2007 — Lost NLDS to Diamondbacks 3-0. 2008 — Lost NLDS to Dodgers 3-0.

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Updated: February 1, 2013 3:30PM

Seventeen months and 122 Cubs losses later, the most successful general manager in Cubs history by most measures can’t get away from one bitter thought when he considers his nine years in charge.

‘‘I still look at myself harshly,’’ Jim Hendry says. ‘‘I think the day I got the job, if you’d have told me six or seven years into it that we’d have won three divisions but hadn’t got to the Series, I would have thought I could have done better. I expected to be the GM when the Cubs got to the World Series . . .

‘‘Sometime in that first six years we should have won.’’

A full season removed from the Cubs, Hendry, 57, is heading into his second year as a special assistant to New York Yankees general manager Brian Cashman, working primarily on scouting and player-development assignments.

A full season into a multi-year rebuilding plan under Theo Epstein, the Cubs are heading into another season of high prices, low expectations, long-term hope and short-term questions about patience.

For all the ownership-churning, payroll-slashing reasons for the Cubs’ recent decline — and the Theo-as-savior sentiment that followed his hiring — it’s easy to forget the franchise is just four seasons removed from the best record in the National League. And nine from having three shots at winning the one game that would have put the Cubs in that elusive World Series.

How long it’ll take the Cubs to return to that competitive level, much less the World Series, was one of the most popular (and unanswered) questions at this month’s Cubs Convention.

And whether Epstein is the guy who eventually makes that happen, one thing is certain: Hendry’s reputation took a public beating on the way out, despite his producing as many playoff appearances as his 10 most recent predecessors combined and creating enough North Side buzz that CC Sabathia once wooed the Cubs as a free agent before signing with the Yankees.

On the way to those 101 losses last year, Hendry was blamed for everything from reckless spending and wrecking the farm system to behind-the-times management methods, feeding a narrative that suggested everything pre-Theo was worthless.

How fair is it? Where does the truth lie?

Hendry won’t point fingers or get into how his legacy is being portrayed.

‘‘I’ve never spent a second worrying about my legacy,’’ he said. ‘‘What I care about is what the people that worked under me thought of me or what my peers think of me in the game. Other things are sometimes written or said without actual knowledge of what really goes on in an organization.’’

Many who know Hendry’s methods first-hand and know the behind-the-scenes realities he faced in his final years with the Cubs defend him — particularly when it comes to criticism that he doesn’t value scouting and player development as priorities.

‘‘It’s not true. It’s quite the opposite,’’ Cashman said of the former college coach and minor-league manager who spent a decade in scouting and player development for the Florida Marlins and Cubs.

‘‘He uses every tool in the toolbox,’’ Cashman added. ‘‘He’s a tremendous evaluator. We ran him into the ground on amateur scouting for the draft and then for the pro scouting.’’

Billy Eppler, Cashman’s assistant GM for pro personnel, worked closely with Hendry over the last year and said it’s also inaccurate to say he doesn’t embrace the same kind of objective-data analytics Epstein is famous for.

‘‘We have an extensive quantitative analysis department,’’ Eppler said. ‘‘He seems to have actually a thirst and hunger for more information.’’

Whatever the criticism, Hendry said he was treated well by Cubs chairman Tom Ricketts and has always had a good relationship with Epstein.

‘‘We had some huge contracts and we tried to win in a hurry when Tribune was going to sell the club,’’ he said, ‘‘and when you don’t finish it off with a ring, it’s easy to say, ‘Well, you neglected this or that.’ If it would have worked, it would have been great.

‘‘But that’s not the way we ran things for years. . . . In a perfect world, especially when you have good finances behind it, you can take a long time and steadily keep building it and pick and choose your ways to go about it in free agency. That’s the ideal way to do it, and it looks like that’s the way Tom and Theo are going about it.’’

Despite the ‘‘worse-than-we-thought’’ comments about the Cubs’ farm system the last year by the new regime — and despite being denied until 2011 the amateur-signing budget to overdraft, as other teams had been doing — the old regime was responsible for signing the top prospect in the system (Javier Baez), All-Star shortstop Starlin Castro and potential Opening Day starter Jeff Samardzija.

‘‘I went through something similar in San Diego,’’ said Arizona Diamondbacks GM Kevin Towers, who was fired after 14 years as the Padres’ GM after the 2009 season and replaced by current Cubs GM Jed Hoyer. ‘‘That comes with the territory. More often than not, when [a regime change] happens, you’re going to only hear the negative. There’s probably some good things and some good players that are there, but you won’t ever hear about that. You’re usually going to hear all the negative.’’

The real negative, according to multiple team sources, was the way a win-now, spend-big mandate from the top in preparation for Tribune Co.’s sale of the Cubs after the 2006 season got torpedoed by new owner Sam Zell’s sudden reversal on promised payroll increases two years later.

By then, the payroll included a half-dozen contracts that were backloaded on orders from Tribune execs who knew somebody else would get the biggest bills — with those execs directly adding years and money to Alfonso Soriano’s eventual $136  million deal. (Business president Crane Kenney boasted privately about closing that deal at the time, according to one source.)

Not that Hendry is without blame. He waited too long to replace his scouting director with Tim Wilken (in ’06). He hired the wrong guy (Mike Quade) to replace Lou Piniella as manager in 2011. And not even Hendry can justify the Milton Bradley signing.

‘‘He’s very loyal — maybe to a fault,’’ said Towers, one of Hendry’s closest friends among baseball executives.

Several well-connected sources say they believe Hendry, a longtime favorite of commissioner Bud Selig, will get multiple opportunities to run a team again, possibly as soon as next season.

‘‘I know people might not think this is true,’’ Hendry said, ‘‘but I really have spent very little time thinking about it.’’

In addition to his duties with the Yankees, Hendry has been able to focus more on family over the last year, with a son and daughter both in high school in the area.

‘‘I feel like the time away from being the GM was helpful, obviously physically and mentally,’’ he said. ‘‘Physically, I feel a lot more energetic and recharged again. So I do believe I could do it again, but it’s not something I really get obsessed over.’’

Nor something he seeks as a way to prove anything or redeem those last few years in Chicago.

‘‘It wouldn’t be about a show-me thing,’’ he said, ‘‘because I was awarded a great opportunity here, and it went fairly well for a long time. I don’t think I need to show people I could do it well again.’’

Until then, he has another year left on his Yankees contract and not a lot of time for regrets.

‘‘I’m very comfortable, I think, with my reputation in the game,’’ he said. ‘‘At the end of the day, that’s all we really have is our reputation. And I’m comfortable in the way I went about my business in my 17 years here.’’

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