In six full seasons as a starter Jackson has pitched for three different playoff teams, reached two World Series (winning one), made one All Star team and just wrapped up a 31 start season for a team with the major's best regular-season record.
On the other hand, Jackson has been traded six times before his 30th birthday and not once did a previous employer lock him up with a long-term contract, or even value him as a franchise player.
Because it turns out Jackson isn't the difference-maker many thought he was, at least not in a postseason caliber rotation. In that case Jackson is simply replaceable on a good team, or better said--trade bait.
IS JACKSON WORTH THE MONEY?
If you look at Jackson's career statistically he's slightly below the league average for starting pitchers (ERA+98). He has, however, proven to be durable, an innings eater and occasionally dominant, and it's the latter which seems to have always made him more attractive to his opponent than he was valued by his own club.
Still, four years from the Cubs is a big commitment for a guy like Jackson. In the short-term and on a crummy team there's little doubt Jackson won't add value to the rotation and some credibility to the rebuild's progress. He would also be a much needed security blanket if the Cubs eventually trade Matt Garza next season.
But I'm more concerned with the long-term outlook than I am about the dollars Jackson is receiving. What value will an average pitcher still owed 2 years, $26 million bring you in 2014 when the Cubs project to be fielding their first truly competitive squad of the rebuilding era?
WILL JACKSON BE TRADED AGAIN?
The Cubs' new regime has been resistant to offering no-trade clauses. Not surprisingly, Jackson's deal is reportedly without one.
The years, and particularly the money, remaining on his contract certainly doesn't make him any more appealing via trade. But that's a bridge the Cubs will have to cross with Jackson when they get there. Jackson of course has been traded plenty of times before, but never has his contract outweighed his potential the way it does now.
DID THE CUBS MAKE A WISE INVESTMENT OR DESPERATE MOVE?
The Jackson signing is the first offseason move by the Cubs I don't fully understand, even though he's the most talented player the Cubs have landed this winter.
My gut feeling is the value Jackson will add to the Cubs won't make much difference on a team still two or three season out from contending.
I question if using the $52 million on Jackson couldn't have been better invested in a higher prized pitcher, say two or three years from now through trade or free agency. That kind of cash could be a huge advantage in the Cubs netting a player who could be the difference-maker in Chicago reaching the postseason.
It feels like the Cubs overextended themselves with Jackson, although I do appreciate the aggressiveness to improve the team for next season. One way or another, four years from now we'll look back on this signing as Team Theo's first big mistake or the first big splash during the rebuild.
Either way, I can't wait to find out.
Brian Corbin is a Chicago-based sports blogger and passionate Chicago Cubs fan. He's covered the Cubs year-round since 2007 on his blog BullpenBrian.com. His posts have been published on the Chicago Sun-Times News Group web sites and numerous baseball blogs.
You can follow Brian on Twitter @bullpenbrian.