Is new Cubs pitcher Lester worth $155 million? Hell yes!

  • Written by Bob Rakow

On Oct. 2, 1984, my college buddy Paul Gember bought a used car and was itching to drive. He sat with me in the lounge at Moraine Valley Community College practically begging me to ride with him.


I wouldn’t budge. The Cubs were about to play in Game 1 of the National League playoffs and nothing was keeping me from watching the game. I wasn’t missing a pitch. This was a rare occasion—Cubs and playoff baseball. It was not to be missed.


Just a week earlier, I lugged my boom box to work so I could listen to the Cubs clinch the National League East with a win in Pittsburgh. I was washing pots and pans at Jenny’s Smorgasbord in Oak Lawn (later the Harley-Davidson shop) and listened to the last few innings after the eatery closed.


What a moment.


The team that lost every year since I began following them as a young boy won a division. Rick Sutcliffe threw a two-hitter. What a gem. The ace that had been acquired from the Cleveland Indians carried the Cubs that year.


When I wrapped up the pots and pans that glorious night, I walked out of the restaurant to my dad’s waiting car.  I don’t remember what we said to one another, but it was one of those perfect moments. He’d waited nearly 40 years for the Cubs to do something, anything. He suffered through 1969.


We relished the moment.


Back to Paul Gember’s new car. He would not take no for answer and offered the ideal compromise. "I’ll drive us to Wrigley Field," he said. "You’re on,'' I told him, and we made the trek from Palos Hills to Wrigleyville listening to the Cubs game on the radio.


When we got there, we managed to get into a bar, and when the game ended, a woman poured a beer over my head. Cubs, 16, San Diego Padres, 6. Sutcliffe hit a home run. I was ecstatic. Wet, but ecstatic.


Five days later, I was bummed. The Cubs lost three straight games to the Padres, who were led by Steve Garvey. The final game was on a Sunday. I’ll never forget my dad cooking or baking something in the kitchen and refusing to watch the game. It hurt bad.


There have been other Cub playoff appearances, and they were disappointing. But nothing hurt like 1984 and the ball rolling under Leon Durham’s mitt. That was 30 years ago and I remember it like yesterday.


I thought about the Cubs joy and pain my dad and I suffered last week over the years when I texted my son with the most exciting news I’ve had as a Cub fan in several years. “The Cubs got Lester,” I texted. He knew already and held off texting me the news because he thought I had gone to bed.


Lester is Jon Lester. The top pitching free agent in the 2014 crop. He’s the guy who signs the first free-agent pitching contract so terms can be established for all the other free agent hurlers out there. Lester, as sports radio host Chet Coppock would say, sits atop the big, rock candy mountain. The crème de la crème.


The Cubs paid dearly to get him—six-years, $155 million dollars. Lot of money? You bet. Worth it? In the Cubs case, hell yes.


Lester is a winner. The kind of guy who could carry a team. He spent most of his career with the Boston Red Sox. Won the World Series with the team in 2007 and again in 2011. He spent part of last season with the Oakland A’s, but the baseball world has known for months that the he would be the prime free agent in the off-season.


And now he’s a Cub. I have trouble wrapping my head around that notion. Chicago teams, not just the Cubs, typically do not get the top players. They pay lip service to free agency while the Yankees, Cardinals, Red Sox and Angels among others are serious about winning and willing to spend the money needed to be competitive.


On the afternoon before he signed, four teams were still in the running for Lester’s services: the Cubs, Boston Red Sox, Los Angles Dodgers and San Francisco Giants. Later in the day came word that the California teams were out of the running. Just as well. The Giants are the world champs and the Dodgers have the best pitcher in baseball.


So, Lester’s choices were to return to Boston—familiar territory where he’s had success and the fans love him—or take a chance in Chicago, where something is about to happen. Where Theo Epstein tore the whole ugly, losing mess to the ground and gathered top prospects that are finally ready to play in the big leagues.


Oh yeah, along the way he added one of the game’s best managers in Joe Maddon.


Some Cubs ripped Epstein over the past few years for his rebuilding strategy. They were sick of losing and argued that Epstein needed to sign some veteran players as soon as possible to make the team respectable. They wanted the short-term fix. Epstein wanted a team that is in a position to win every year. See the Chicago Blackhawks as an example.


Epstein was patient. He’s endured several losing seasons but introduced us to Starlin Castro, Javier Baez and Anthony Rizzo on the major league level plus Kris Bryant and a host of others on the minor league level.


Addison Russell, the A’s top prospect, was brought to Chicago in a late-season trade last year. Last summer, the Cubs had four of the top 15 prospects in baseball, according to, and eight among the top 100.


The future is bright. The future is now. Talk of the Cubs winning in a few years should be put to bed. Jon Lester doesn’t get signed so the team can win in 2017. Epstein just upped the ante. Lester is likely not his last off-season move.


It’s an exciting time to be a Cubs fan. Opening Day is April 5.