History Tells Us Signing Jon Lester to a Massive Deal Justifies Playoff Hopes

Jon Lester signed a 7-year, $155 million contract to leave the Oakland A’s and pitch for the Cubs less than a month ago, creating instant optimism among Cubs fans. And why not? People talk about these big contracts like they’re a huge risk, and they are. But I started wondering what historical precedent there was to determine how good we should feel about what the near future holds for our Cubbies.

So I went digging to find the largest free agent contracts in baseball history in order to look at a few different things: win totals the year before and after the deal, other notable changes with the roster, and average win total of teams after signing a player to a massive deal.

For this exercise, I looked at only guys that signed with a brand new team and I looked at contracts bigger than what Lester was given with the Cubs. A major finding that I thought was interesting was that Lester’s deal with the Cubs is the seventh-largest contract in all of professional sports signed by a player leaving one team for another.

The six that preceded Lester are all interesting tales as well, and I think some of the trends that followed these massive contracts could help inject even more optimism into the hopes for the Cubs’ future. Here are the other six, listed in chronological order.

Manny Ramirez

Manny was just being Manny when he left the Cleveland Indians following the 2000 season to sign an 8-year, $160 million deal to DH for the Boston Red Sox. The Sox were coming off an 85-win season in which they finished 2nd in the AL East behind the World Series Champion Yankees, missing the playoffs after making it the previous two seasons. They were led by shortstop Nomar Garciaparra, who batted .372/.434/.599 in just under 600 plate appearances.

Ramirez didn’t disappoint in his first season with the Red Sox, posting an OPS of 1.014 with 41 home runs. But Boston’s record dropped to 82-79, mostly because Garciaparra and Pedro Martinez were hurt and only played in 21 and 18 games, respectively. You can’t blame the Ramirez signing for the slight drop in wins, and it’s worth noting that the Sox won an average of 93.8 games per season the rest of Ramirez’s time in Boston, which includes two World Series Championships.

Mark Teixeira and C.C. Sabathia

I put these together because they both signed with the Yankees following the 2008 season. The Yankees won 89 games in 2008 and missed the playoffs for the first time since essentially 1993 (they had the best record in the AL at the time of the 1994 strike that canceled the postseason). The Bronx Bombers went into the offseason with the plan of going on a spending spree to put them back into the playoffs, and did they ever.

Sabathia left the Brewers to sign a 7-year, $161 million dollar deal and Teixeira left the Angels for an 8-year, $180 million contract. Teixiera was replacing the departed Jason Giambi, and Sabathia was anchoring a pitching staff that only returned Andy Pettitte from the 2008 starting rotation. The Yankees made other moves as well, signing A.J. Burnett to a 5-year, $82.5 million deal, trading for Nick Swisher, and calling up prospects Joba Chamberlain and Phil Hughes.

The Yankees won 103 games and their first World Series since 2000 that year, in large part because of the contributions of Teixeira and Sabathia.

Prince Fielder

Fielder left the Brewers after a postseason run to the NLCS in 2011 to sign a 9-year, $214 million contract with the Detroit Tigers. The Tigers were coming off of a 95-win season in which they lost to the Rangers in the ALCS, and signed Fielder to play first-base and push the incumbent Miggy Cabrera over to third-base.

The Tigers got a good season out of Fielder in 2012, as he hit .313/.412/.528 while playing all 162 games. However, Fielder’s production had to essentially replace Victor Martinez, who missed all of the 2012 season with a torn ACL. The Tigers won 88 games, which was seven fewer victories than their 2011 record, but still made it to the World Series before losing to the Giants.

Fielder again played all 162 games in 2013, but posted a much more average .819 OPS. After struggling in the playoffs, the Tigers traded Fielder to the Rangers for Ian Kinsler. In the third year of his nine-year contract, Fielder played only 42 games in 2014, hitting .247/.360/.360 with 3 home runs before finishing the season on the DL with a spinal fusion surgery in his neck that has his career in jeopardy.

Albert Pujols

Pujols, like Fielder, left a team that made a deep playoff run in 2011 for the American League. After winning the World Series with the Cardinals, Pujols signed a 10-year, $240 million contract with the Los Angeles Angels. The Angels were coming off of an 86-win, 2nd place finish in the AL West in 2011, and the addition of Pujols helped raise their win total to 89.

Pujols hit .285/.356/.516 with 30 home runs that first year, and although he has been in major decline and is one of the most overpaid players in baseball, the Angels did rally to win 98 games and the AL West division in 2014. The Angels still have seven years left to pay 35-year-old Pujols, who is now just an average first baseman at best.

Robinson Cano

After posting a .309/.355/.504 slash line in nine years with the Yankees, second baseman Robinson Cano left to sign a 10-year, $240 million contract with the Seattle Mariners. He didn’t disappoint in his first season, hitting .314/.382/.454 and helping lead the Mariners to raise their win total from 71 wins in 2013 to 87 in 2014.

Cano is still a very productive player at just 32 years old, but still has nine years left on his contract. The Mariners obviously wanted to try to win right away when they decided to spend the money for him. They had a 16-game improvement from 2013 to 2014 and were in the Wild Card race right up until the final days of the season. They’ll be in the discussion as a potential AL West contender in 2015.

Obviously, there have been varying levels of success in the first year of these big free agent deals. And this has been in no way an attempt to compare long-term success of signing players to massive deals. I think the Yankees, who are still finishing out the Sabathia and Teixeira contracts and are in “84-win purgatory” because of it, are a cautionary tale.

The same could be said of Fielder and his unsure future and Pujols and his massive production drop-off. But the interesting fact is that the average win total the for these teams in the season after laying out these massive deals is 92 games. The Yankees won the World Series the first year after dropping contracts on Teixeira and Sabatha, the Red Sox won two World Series with Ramirez, the Tigers made it to the World Series with first year with Fielder, and the Mariners went from a bottom-feeder to a playoff contender after signing Cano.

While it didn’t make the list, you’ll no doubt recall the Cubs transforming from a last place team in 2006 to the division winner in 2007 after signing Alfonso Soriano to an 8-year, $138 million contract (yes, there were other players as well). My take-away from all this information is that maybe there is more hope for 2015 than just maybe winning 85 games. A 16-game improvement, like the Mariners had with Cano, would bring the Cubs to 89 wins (which would’ve put them in the playoffs last season).

So while we can’t conclude anything scientific from this information, we can at least justify dreaming further about the upcoming baseball season. For the first time in far too long, the Cubs have given us a reason believe. And that belief may not be too far-fetched.

The first A-Rod contract should be on this list too. For whatever reason, the list I used had him on it but listed him as “Yankees” and not Rangers for the contract he signed prior to the 2000 season. In my thought process, I concluded that he was traded to the Yankees, so that it didn’t count. My apologies for the error.

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