Can Cubs fans embrace John Lackey? Only if he wins.

By Randy Richardson

Google “John Lackey personality” and you get descriptions that range from “intense” and “bombastic” to “a wet mop.” And those are some of the nicer things. Some of the characterizations you’ll find are not suitable reading for younger audiences.

What you won’t find associated with the Cubs’ newest starting pitcher are words like kind, pleasant or humble.

You get the idea. Lackey, the veteran hurler acquired last week by the Cubs in a two-year, $32 million deal via free agency, is not generally seen as being a nice guy.

But should that matter? Does niceness count in baseball?

The famous baseball quote, “Nice guys finish last,” has long been attributed to Leo Durocher, who managed the Cubs from 1966 to 1972. Nicknamed “The Lip,” Durocher was a fiery skipper known for kicking up a lot of dust. Durocher probably would have liked to have had a guy like Lackey pitching for his team.

Contrast that with the Cubs’ current manager, Joe Maddon, whose likability rating is through the roof. The fans, the players, even the press – they’re all smitten with him. He’s a nice guy, and as he’s shown, over and over again, he doesn’t finish last.

Over the last four years, Theo Epstein, the Cubs’ president of baseball operations has carefully constructed a baseball team that is younger, more talented, and, yes, nicer than most teams of Cubs’ past. He almost seems to go out of his way to choose the kind of players and coaches who are good guys.

It started with Anthony Rizzo, one of Epstein’s first trade acquisitions, a player who seems to spend much of his free time at a children’s hospital, hanging out with kids who have cancer. Rizzo is extremely active in the battle against cancer, using the Anthony Rizzo Family Foundation to “raise money for cancer research and to provide support to children and their families battling the disease,” according to the foundation’s website. Rizzo himself is a cancer survivor, having battled Hodgkin’s lymphoma while a member of the Boston Red Sox organization in 2008.

Look at some of the other Epstein acquisitions. Last year through free agency he reeled in pitchers Jon Lester, who started his own foundation, NVRQT, short for “Never Quit,” to support pediatric cancer research, and Jason Motte, who runs two foundations, the Jason Motte Foundation, and a cancer awareness foundation called “Strikeout Childhood Cancer.”

You get the idea. Character matters to this team. Or at least it did.

The acquisition of Lackey seems to be, well, almost out of character for the Epstein Cubs. Of course, this isn’t the first go round for Epstein and Lackey. It was Epstein, then as GM for the Red Sox, who signed Lackey to his first free agent contract in 2009. Fans in Boston had a love-hate relationship with Lackey. Mostly it was hate, at least until the end, spurred by the chicken-and-beer incident of 2011.

You remember the chicken-and-beer incident, right? In the end of the 2011 season, Lackey and two more starting pitchers (Josh Beckett and Jon Lester, allegedly) were in the center of a controversy that told that the three (and sometimes more) drank beers and ate fried chicken in the clubhouse during games in which they were not pitching. Lackey didn’t help his public relations cause when he sat out the entire 2012 season following Tommy John surgery and was later seen drinking beer in the clubhouse during his rehabilitation.

There are other more personal and more troublesome stories from Lackey’s recent past that can be easily found through your own Google searches but don’t need to be rehashed here.

Given his questionable character one has to wonder: What does Epstein see in him?

Surely Epstein knows him well enough to know what he’s getting. And the two players on the current Cubs’ team who had been teammates with Lackey during his Boston days have nothing but positive things to say about him.

Indeed, Lester, who had been caught up in the chicken-and-beer controversy with Lackey, is so close to “Lack”, as he calls him, he looks to him as both a mentor and a friend. “Our friendship will go beyond this game,” Lester said in October, “it will go beyond our careers, and it’s something that means a lot to me.”

Both Lester and catcher David Ross, who had also played with Lackey in Boston, cite to his fierce competitiveness as a positive influence. “One of the best competitors I’ve ever been around, and I’m not just saying that,” Ross told ESPN.com last week. “He’s going to bring a toughness to our team that is going to make everybody better.”

Mostly what Lackey brings, along with that competitive edge, is a winner’s mentality. He has pitched in eight postseasons with three different teams, including winning two World Series championships, in his rookie 2002 campaign with the Angels and in 2013 with the Red Sox. In both of those World Series titles he pitched the clinching game. He’s a gamer.

Take that history of winning when it counts, the 13-10 with a 2.77 ERA during his age-36 season with the St. Louis Cardinals last season, and the price tags of top tier free agent pitchers David Price and Zack Greinke, and the Cubs’ signing of Lackey starts to make some sense. Sure he comes at the cost of a first draft pick, in addition to the $32 million over two years, but he’s probably the best short-term bet for a franchise in win-now mode.

Indeed, Josh Benjamin of Forbes.com called the move “borderline perfect,” writing that “Lackey brings to Chicago what the pitching staff so desperately needs: veteran leadership.”

Patrick Mooney, writing for CSNChicago.com, agreed that “Lackey makes a lot of sense if the Cubs want to avoid a risky long-term commitment, save some bullets for the future and upgrade their rotation with a reliable veteran starter who has a career 3.11 ERA in 127-plus postseason innings.”

Perhaps the biggest question mark surrounding Lackey is his age. Will he be able to maintain the level of pitching he achieved this year as he reaches into the upper-30s.

Ross, who has caught Lackey in the past and had to hit against him this past season, thinks Lackey has what it takes. “He has gotten better since I last caught him,” Ross told the Tribune Friday. “He has a sharper slider and a cutter, and he still dominated back then. I think we have three No. 1 (starters).”

Al Yellon of bleedcubbieblue.com was less optimistic. “Let’s just say I’m somewhat skeptical that this will work,” he wrote last week. “I hope I’m wrong.”

The last time Lackey pitched was of course against the Cubs in the NLDS. We saw the best of him and the worst of him. In Game 1, he looked like the Lackey of old, holding the Cubs hitless through the first five innings on the way to pitching 7 1⁄3 shutout innings in a 4–0 win. But then in Game 4, pitching on just three days’ rest, he looked his age, especially when Cubs’ rookie Javier Baez drilled a three-run home run off of him that helped Chicago win the game and the series.

Overall, Lackey would seem to be an upgrade over Dan Haren, whom he essentially replaces on the roster.

And Chicago fans do have a history of embracing the unlikeable – as long as they win. Look no further than Dennis Rodman of the Bulls and A.J. Pierzynski of the White Sox, two of their sports’ greatest villains who became heroes in Chicago when they brought championships to the city.

It seems a safe bet that if Lackey can do for the Cubs what Rodman and Pierzynski did for their Chicago teams, all his sins of the past will be forgiven, at least by Cubs’ fans.

Randy Richardson is the author of the Wrigleyville murder mystery, Lost in the Ivy, and a regular contributor to Wrigleyville Nation.