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Ultimate Cubs Lineup: Ryan Dempster

4 years agoTony Andracki

What if you were tasked with winning one — and only one — baseball game and you were responsible for putting together the lineup to get you that W?

Here’s the thing: You can only form the lineup from guys who have suited up for the Cubs, even if it was for only one game or part of one season. This isn’t a list of the greatest Cubs players. It’s the Ultimate Cubs Lineup to win one big game.

That means you can select Mordecai “Three Finger” Brown (who pitched for the Cubs from 1904-1912 and again in 1916) or Anthony Rizzo (who led the Cubs to end the 108-year World Series drought).

You can choose Hall of Famers, All-Stars, role players, whoever. You can prioritize power, contact, defense, intangibles or whatever you think is necessary to win this one imaginary game. You can even hit the pitcher 8th or anywhere you see fit in the lineup.

Since the Cubs are a National League team, we are forming the roster with no designated hitter. To add another wrinkle of strategy, you can select one reliever to come in after the starting pitcher and one player off the bench who could come into the game at any point.

So which 11 current or former Cubs would you choose to go to battle with in a must-win game?

Marquee Sports Network’s Ryan Dempster weighs in:

1. Reed Johnson – CF
2. Ryan Theriot – SS
3. Aramis Ramírez – 3B
4. Derrek Lee – 1B
5. Moisés Alou – LF
6. Mark DeRosa – 2B
7. Jeromy Burnitz – RF
8. Geovany Soto – C
9. Jon Lester – P

Reliever: Kerry Wood

Bench: Tom Goodwin

Dempster’s rationale

I went with players that I actually played with on the Cubs. I could sit here and argue who’s better — Gabby Hartnett or Willson Contreras or something like that. But I wanted to go with guys who I actually played with so I had a firsthand experience with their passion, their ability and what I saw out of them.

Now, a lot of people would say there’s probably better centerfielders in Cubs history — I dunno. When I was on the mound, I didn’t know too many outfielders who were better than this guy. The catch he made in Washington or robbing Prince Fielder’s grand slam in Milwaukee. At the plate, he was going to find a way to get on first base.

Theriot played a ton of years behind me at short. He battled being the underdog as a shorter ballplayer, but he played with that chip on his shoulder and that edge. He went on later in his career in back-to-back years with the St. Louis Cardinals and San Francisco Giants, so he’s proven that on the biggest stage, he knows what it takes to win.

Ramírez can absolutely rake. When the games got more intense and meant more, he actually got better. A Tuesday in Pittsburgh in the middle of June didn’t do much for Aramis, but a September game on the grandest of stages, he lived for that. He also lived for RBIs. Out of all the players I played with on any team, he was an RBI machine. He was the most clutch with runners in scoring position. He found a way to turn the notch up. A deadly, deadly focus and he was pretty wicked with the glove.

First base was the toughest choice I had because I played with Anthony Rizzo in 2012 and he was a good, young ballplayer at that age, but he hadn’t come into his own yet. So I went with somebody I played with a lot over my career in Lee. I watched what he did in 2005 when he could’ve been the MVP and won the batting title. He put on a pure display and to this day, there’s nobody better at first base than D-Lee — big man, big target, big glove, an absolute stud.

Alou, to me, is the godfather — a calm, silent leader by example. He could turn on anybody’s fastball and lived for those big games and big situations. He won a World Series with the Marlins and played on plenty of playoff teams in Chicago and other places along the way. He was a tremendous hitter and that father figure over all of us to kind of keep us all intact.

The thing I loved about DeRosa was his versatility to be able to play right field or left field or second base or shortstop or third base. But he loved second base and he was a really good defender with great footwork around the bag, turned two with the strong arm. He was poised and was our best offensive player in the 2008 playoffs. I knew when a big game would come, he would be prepared, focused and determined and that’s what you want out of somebody.

I thought about Sammy Sosa in right field (I played with him for a year), but I played with Burnitz for a couple years on the North Side. The thing I loved about him was I would love to have prime Jeromy Burnitz bat with the kind of defense he played as a Chicago Cub. This guy went out every first group of BP and absolutely went bananas trying to get after it.

Soto caught as many of my starts as Cub as anybody. He would always go out there and do whatever he had to do to try and help his team win and get the best out of his pitcher.

Now, for starting pitcher, I could’ve picked myself. It seems like it would make sense — I believe in myself, I trust myself. But when it comes down to winning one game, I went with somebody I played with not on the Cubs but also is a Cub currently — the big left-hander Jon Lester. A three-time World Series champ, his dominance in the playoffs has been unmatched. He signed a long-term deal to bring a championship to the North Side of Chicago and he didn’t disappoint. Right now, today, I would have him be my guy that I would start that must-win game. If there’s one thing I won’t do, I won’t doubt Jon Lester on the biggest stage in the biggest situation.

In 2008, I went from the bullpen to the starting rotation while Wood went from the rotation to the bullpen. Anybody who can punch out 20 guys in a game as a starter, what can he do as a closer? Well he can be absolutely dominant. I wish I would’ve had him as our closer in Chicago for a long time — he was nasty and he was intimidating.

Goodwin kept the locker room loose and the dugout fun. He kept guys on their toes, kept guys honest and made sure you were hustling. He was a leader in that locker room and on that bench. Every Sunday when they played all the extras and the scrubs (the “lemons”), he would say: “Oh, the lemons are coming, boys. We’re making lemonade today!”

Be sure to check out all of our Ultimate Cubs Lineups!

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