The Cubs won the most games they had in a single season (97) since 1945. With it being the 100th anniversary of the last World Series win, it was hoped... but nope, all that got the team was a division series sweep at the hands of the Dodgers.
And only a handful of trades were made.
January 5: Acquired Corey Coles and Ryan Meyers from the Mets for Angel Pagan
Pagan had been a decent part-time player for the Cubs in 2006 and 2007, but he immediately became the starting center fielder in New York, and eventually played on two postseason teams in San Francisco, winning a World Series ring in 2012 (he got one in 2014 too, but injuries kept him out of the postseason that year).
The Mets got 10.8 bWAR from Pagan and the Giants 6.5 bWAR, though his defense declined after 2010.
The Cubs got nothing from this deal, as neither of the players received ever played in the major leagues. This was not a good trade.
July 8: Acquired Rich Harden and Chad Gaudin from the Athletics for Sean Gallagher, Eric Patterson, Matt Murton and Josh Donaldson
This was a great deal, for a while. Harden made 12 really good starts for the Cubs in ‘08 but wasn’t quite as good in ‘09 and left as a free agent, having given the Cubs 5.1 bWAR. He played just two more MLB seasons, injuries ruining what could have been an excellent career. Harden was probably THE top player being sought at the trade deadline that year and the Cubs had to offer a large package of players to get him — other teams were in the running. In 2008, he posted a 1.77 ERA with 89 strikeouts in 71 innings.
Gaudin posted a 6.26 ERA in 24 relief appearances and was released just before Opening Day 2009.
The key to this deal was actually Gallagher, who had been a Top 100 MLB prospect before 2008 and had dominated everywhere he’d been in the Cubs system. He didn’t pitch well in 20 games (10 starts) for the Cubs in 2007 and 2008 and was out of MLB with a 5.64 career ERA after 2010, including stops in San Diego and Pittsburgh. He hung around in indy ball until 2016.
Eric Patterson and Matt Murton were also considered at least useful pieces at the time, but neither did much in the majors after the deal, Murton eventually posting some good numbers in Japan.
Anyone who looks at this deal and tells you the Cubs gave up on Donaldson too early is practicing revisionist history. Yes, Donaldson had been a No. 1 pick (48th overall) of the Cubs in 2007, but at the time of the deal he was a catcher hitting .217 at Low-A Peoria. There was absolutely nothing in his minor-league record at that date that would have suggested he’d win an MVP Award (American League, 2015) or hit 279 MLB home runs as (mostly) a third baseman. Kudos to the A’s for figuring that out, though it was the Blue Jays who got his best years.
That’s a 46.8 bWAR career the Cubs traded away. Whether he’d have done anything close to that for the Cubs is a question we’ll likely never be able to answer.
August 7: Acquired Brian Schlitter from the Phillies for Scott Eyre
At the time, Schlitter had not pitched in the majors and indeed, wouldn’t until 2010 for the Cubs.
The guy Lou Piniella called “Stevie Air” had pitched reasonably well for the Cubs in 2006 and 2007, but his numbers had declined in ‘08 and Lou lost confidence in him. Immediately after the trade, he made 19 appearances for the Phillies with a 1.88 ERA and 0.767 WHIP and had a good year for them in ‘09 as well, giving them 1.7 bWAR. The Cubs probably should have kept him.
Schlitter pitched almost everywhere on Earth — from two stints with the Cubs to a year in Japan to a couple years in the Mexican League. He was still active in 2023 (!) with the Chicago Dogs indy league team, posting a 3.24 ERA with 18 saves. Fun fact: He’s 13 days younger than Josh Donaldson.
November 3: Acquired Ryan Buchter from the Nationals for Matt Avery
This sounds like another made-up deal but it’s not. Avery was the Cubs’ ninth-round pick in 2005 out of the University of Virginia. He never pitched in the majors.
And Buchter never pitched for the Cubs. He was traded away in a deal we’ll cover later on and pitched seven years in the majors in 2014 and 2016-22 for the Braves, Padres, Royals, A’s, Angels and Diamondbacks, for a total of 3.9 bWAR. He was briefly reacquired by the Cubs in mid-2015, but was let go again after the year after posting a 2.00 ERA in 16 games at Triple-A Iowa.
Another guy the Cubs probably should have just kept.
November 13: Acquired Kevin Gregg from the Marlins for Jose Ceda
After it was clear the Cubs were going to let Kerry Wood walk in free agency, Jim Hendry acquired Gregg to be the Cubs’ closer, and to be charitable, he had a bad year. Gregg posted a 4.72 ERA with 23 saves in 2009 — but also had seven blown saves and was replaced as closer by Carlos Marmol, which maybe the Cubs should have just done in the first place. Gregg left as a free agent after the season.
Ceda posted a 4.66 ERA in 25 appearances for the Marlins in 2010 and 2011.
Oddly, a completely different Cubs management regime re-signed Gregg as a free agent just before the 2013 season and he had a better year — a 3.48 ERA and 33 saves in 38 opportunities. Overall he gave the Cubs 0.6 bWAR in those two seasons.
December 31: Acquired Chris Archer, John Gaub and Jeff Stevens from the Indians for Mark DeRosa
This is a “What were you thinking?” kind of deal. DeRosa had just had two of his best years for the Cubs, playing just about everywhere on the field and contributing 4.0 bWAR, as well as being a popular fan favorite.
Gaub didn’t pitch for the Cubs until 2011 and then in only four games, posting a 6.75 ERA. Stevens had a 6.27 ERA in 33 appearances for the Cubs from 2009-11.
This deal might have worked out all right if the Cubs had just kept Archer instead of trading him away two years later. It turned out Jim Hendry was more or less right about DeRosa — he played four more years for Cleveland, St. Louis, San Francisco, Washington and Toronto, but was injured and missed a lot of time in those years. I assume the Giants gave him a ring in 2010 even though he didn’t play in the postseason.
All in all, this was not a good year for Cubs trades. Some of them could have worked out differently — but in the end, they didn’t. Grade: D
EDITOR’S NOTE: This series will resume on Monday.
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