Thus, he'll be able to walk away from the game of baseball knowing that he did well even if the Cubs don't win another game under his watch.
But as I and many others have written before, Epstein is going for broke with the Cubs. He doesn't want to be one of the greatest executives in baseball history. He wants to be the greatest executive in baseball history.
If he ends up leading both the Red Sox and Cubs to world titles, he will have earned that title.
It won't be easy. Epstein didn't have to build a winner from scratch in Boston, and that's what he's attempting to do in Chicago. He's trying to build a World Series winner from the ground up.
Though Epstein's experience in Boston didn't necessarily teach him what to do in Chicago with the Cubs, he should know what not to do. He made plenty of mistakes during his tenure as the general manager of the Red Sox, and he needs to avoid making those mistakes in Chicago.
Let's look at a few examples.
No Knee-Jerk Trades
During his tenure in Boston, Epstein made a name for himself by knowing when to draw the line with money and knowing when not to show loyalty. He was viewed as both shrewd and bold.
Case in point, Epstein let Pedro Martinez sign with the New York Mets for four years and $53 million after the 2004 season. It looked like a major misstep when Pedro won 15 games for the Mets in 2005, but that was the high point of his Mets career. Just as the Red Sox feared he would, Pedro broke down.
Epstein also made a bold and ultimately smart call by trading away Nomar Garciaparra in 2004. He was able to shore up the team's defense by adding Orlando Cabrera and Doug Mientkiewicz, and the Red Sox took off soon after that trade was made.
For all his cunning, however, there were times when Epstein made deals that a fan would have made, and some of them ended up having disastrous consequences.
The big one that comes to mind is the trade Epstein made to reacquire backup catcher Doug Mirabelli from the San Diego Padres in 2006. He gave up Cla Meredith and Josh Bard for Mirabelli, whose only use to the Red Sox was as a personal catcher for Tim Wakefield.
Mirabelli performed that job just fine after rejoining the Red Sox, but Meredith and Bard both went on to be key contributors for a Padres team that won 88 games and made the playoffs. The Red Sox went home when the regular season was over.
Epstein made another dumb trade in 2007 when he dealt David Murphy and two minor leaguers to the Texas Rangers for Eric Gagne. Though they managed to win the World Series anyway, Gagne was a disaster for the Red Sox. These days, Murphy is arguably the best fourth outfielder in baseball.
Epstein's worst trade, however, came in 2003. That year, he gave up two minor leaguers named Freddy Sanchez and Mike Gonzalez to acquire Jeff Suppan from the Pittsburgh Pirates (Gonzalez had been acquired from Pittsburgh in a previous trade).
Instead of stabilizing Boston's rotation, Suppan posted a 5.57 ERA and a WHIP over 1.40. The American League did not agree with him, and the Red Sox ultimately chose to leave him off their postseason roster.
Sanchez went on to win a batting title, and Gonzalez was one of the top lefty relievers in baseball for a time.
All three of these trades were made to provide the Red Sox with quick fixes, and all three of them had disaster written all over them. In all three cases, Epstein surrendered talented young players he should have held on to.
Epstein could afford to make these mistakes with the Red Sox because their major league roster was consistently very strong and because the team's farm system was also consistently strong during his tenure. It's going to be at least a couple years before he has those same luxuries in Chicago, and even then he should think twice before making quick-fix trades.
Don't Trade Pitching For Hitting
The saying goes that you can never have too much pitching. This saying has proven to be true over and over and over again.
Before the 2006 season, the Red Sox happened to be blessed with too much pitching. At least, such was Epstein's assessment, and he used that as an excuse to trade Bronson Arroyo to the Cincinnati Reds for Wily Mo Pena.
The previous season, Arroyo had won 14 games with a decent 4.51 ERA. Pena had hit .254 with 19 home runs in part-time duty.
Pena wasn't bad for the Red Sox in 2006, but they were definitely missing Arroyo when they resorted to starting guys named Kyle Snyder, Lenny DiNardo, Kason Gabbard and David Pauley. It took precisely five seconds that season for the Red Sox to go from having an excess of pitching to having a shortage of pitching.
Arroyo won 14 games again in 2006 and pitched a career-high 240.2 innings.
So here's a good rule of thumb for Epstein to abide by in Chicago: Don't ever trade a quality pitcher for a quality hitter.
However, here's a disclaimer: The Cubs are rebuilding now, so they don't have a ton of incentive to hold on to, well, any of their players. Epstein can go right ahead and deal Ryan Dempster, and he should also consider dealing Matt Garza. He'll be able to get prospects for these guys, and at this point it doesn't really matter whether he gets pitching or hitting prospects.
The don't-trade-pitching-for-hitting rule of thumb will kick in once the Cubs start winning games on a consistent basis.
Assuming that happens, of course.
Don't Give Tons of Money to Talented Guys Without Numbers
Epstein's best free-agent signings in Boston were the small ones. David Ortiz was signed for a small sum before the 2003 season, as were guys like Bill Mueller and Hideki Okajima later in 2007. Even the Adrian Beltre deal in 2010 wasn't all that big.
Epstein was able to sign quality players for cheap because they didn't have the numbers to demand more money. The idea with signings like these was simple: High reward, low risk.
That's Baseball Business 101.
Because Epstein very clearly knew this, it's ridiculous in retrospect how many times he dished out big paychecks to guys who didn't have the numbers to demand big paychecks.
Exhibit A: Julio Lugo. Epstein signed him for four years and $36 million before the 2007 season, which was a lot of money to pay for a guy who was a .280 hitter with merely decent power between 2003 and 2006 (Baseball-Reference.com has the averages).
Epstein was banking on Lugo being more talented than his numbers suggested he was. It turns out his numbers did him proper justice, as Lugo was a massive bust for the Red Sox both at the plate and in the field.
Epstein made a similar mistake when he signed Matt Clement ahead of the 2005 season. Clement was decent in the National League, but he never put up numbers worthy of a $25 million contract.
But that's what Epstein gave him, and in return he got 44 starts and a 5.09 ERA over parts of two seasons. Granted, Clement's Red Sox career got off to a decent start, but he was never the same after taking a line drive to the head in 2005. Shoulder surgery in 2006 all but ended his career.
Daisuke Matsuzaka is another guy who could fit into this discussion, but Epstein can be forgiven for that signing because of his absurd numbers in Japan.
And yes, he gets a pass for Jorge Soler too. The Cubs may be on the hook for $30 million when it comes to Soler's contract, but that doesn't look so bad when spaced out over nine seasons.
I can take that as a sign that Epstein has learned his lesson about dumb contracts for unproven players, but we won't know for sure until he starts hitting the free-agent market to bolster contending Cubs teams a few years down the road.
Don't Give Tons of Money to Guys Whose Numbers Are CLEARLY in Decline
You know where I'm going with this one, right?
Yup, John Lackey.
Lackey was the top starting pitcher on the market when Epstein signed him before the start of the 2010 season, but that's only because there wasn't much competition. Lackey hadn't pitched over 200 innings since 2007. His stuff was on the decline and his ERA was on the rise when Epstein gave him a contract worth $82.5 million over five seasons.
Lackey has been a disaster for the Red Sox. He was at best decent in 2010 and was one of the worst pitchers in baseball in 2011. This season, he's on the shelf recovering from Tommy John surgery, and he is not missed.
He wasn't that bad in 2008 and 2009 when he was still with the Los Angeles Angels, but it was clear that Lackey's best days were behind him. Whoever signed him was going to be making a bad investment, and that somebody just so happened to be the Red Sox.
Epstein should have known what the score was. Instead, he made yet another move that a fan would have made.
Don't Give Tons of Money to Guys Who Don't Fit at Home
In addition to taking a look at Lackey's falling numbers in 2008 and 2009, Epstein could have taken a long look at his career numbers at Fenway Park before offering him a contract.
Per ESPN.com, Lackey had a 5.75 ERA at Fenway before signing with the Red Sox. He was facing pretty dangerous Boston offenses in those starts, but it didn't help that he was a fly-ball pitcher pitching at a park where the most innocent fly balls can result in home runs.
He was a bad fit at Fenway, plain and simple.
The same is true of Carl Crawford. He never excelled at Fenway when he was a member of the Tampa Bay Rays, and he didn't excel at Fenway in his first season with the Red Sox in 2011.
And it's not hard to determine why. Fenway caters to lefty hitters who can go the other way with authority, and that's not Crawford's game. He has pop, but he's at his best when he's hitting line drives into the gaps. Fenway Park isn't made for such hitters.
Fortunately for Epstein, Wrigley Field doesn't present the same kind of specific challenges that Fenway Park does. It's not an unorthodox ballpark.
One thing will always be true about Wrigley, however, and that's the fact that it's a park that favors hitters. The ball flies out of the yard fairly easily, oftentimes aided by the wind.
Epstein needs to remember what he learned from the Lackey debacle. He should steer clear of fly-ball pitchers and go for strikeout artists and ground-ball pitchers.
For his offense, he should find as many sluggers as he can. To that end, he's on the right track with players like Anthony Rizzo and Brett Jackson down on the farm and Albert Almora and Jorge Soler soon to join them.
It's early yet, but Epstein has the Cubs organization as a whole on the right track. It will be a few years before the Cubs are ready to contend, but you can rest assured that they will be good again.
When those days come, Epstein is going to be tempted to make the mistakes we just discussed, so stay tuned.
If you want to talk baseball, hit me up on Twitter.