He so wanted to return to Major League Baseball that he may have agreed to hold the clipboard for a team that resembled a traveling circus or called the shots at a club better fit for a comedy show.
He got the Red Sox.
Boston's season has been so wild and varied that it's hard to know which parts are true and what just needs to be put to bed for winter, waiting to see what sprouts out of the ground when spring comes.
When last year ended, it was Terry Francona's fault, then Theo Epstein's. Both went. This season, Kevin Youkilis was a problem, and Josh Beckett was at the end of some pointing fingers. Adrian Gonzalez even got some flak, and Carl Crawford was, of course, injured. They are all gone now, too.
The cries for Valentine's head have intensified, but if this year has taught Red Sox fans anything, it's that conclusions are maddeningly difficult to come to.
If Beckett and Gonzalez were a problem of any kind, how do you explain the lack of rejuvenation after they left, as Boston has gone 0-5 on the West Coast, being outscored 48-13? Bob McClure is done hanging his hat in the clubhouse, but the pitching has not become any better. The murmurings of clubhouse discord happen whether Francona or Valentine is filling out the lineup card.
The quick answer, of course, is that change takes time. The Red Sox are left shorthanded as they finish out this season, and a team can't be expected to rip off dozens of wins when several of its best players have just been flipped for prospects who are either in Triple-A or have yet to arrive. The massive trade from last weekend that will mark the Red Sox' direction going forward cannot be judged in the next 30 games. That would be both unfair and insane.
Still, Valentine has been under fire all season, and he will only hear more as a dreadful season wraps up. For all his skills as a manager — and for whatever he did to keep the team above water as long as he did — he will be judged on whether he can pull bunnies out of hats down the homestretch and turn the likes of Pedro Ciriaco, Mauro Gomez, Jose Iglesias and their minor league friends into major league-changing producers.
But Valentine's tenure with the Red Sox can't be judged on the next few weeks of baseball, and there's a good case to be made that it shouldn't be judged on several stretches of this past season, either. If anything, Valentine has had to deal with the worst of worsts, with little chance to show the skills that have made him a good manager before.
The Red Sox may have been a poor place for Valentine to try to manage again, and whether the team is the right fit going forward is a good question, too. That's for Red Sox management to decide. But however Valentine's time in Boston turns out, this shouldn't be the end of a managing career for a man who has shown he still has something to bring if given the right opportunity.
As the Red Sox absorbed another rough pair of losses this weekend, this time in Oakland, Valentine showed considerably less fire and pizzazz than he has throughout the season, when he was ready to quip and joke no matter what odd situation arose. Alex Speier of WEEI writes that Valentine seems to have finally lost the interest, emotion and motivation he needed to stay alive this season as the Red Sox found new ways to get worse.
But that fatigue reveals why this season has been so hard for Valentine, and so unreliable for showing whether Valentine can still be a marquee manager at the MLB level.
Valentine's greatest strengths lie in his charisma and positive nature, where he can rally a team of young players or jump into a new situation and start a turnaround. In Boston, he dealt with a lot of entrenched roles and scenarios, whether it be veteran players (no one's fault) or perceived miscommunication that left Valentine on his heels coming in. The Red Sox of the future may actually suit Valentine far better than the Red Sox of spring 2012 ever would, with young, moldable players coming up and new schemes needing to be employed. Valentine is at his best when he can retool and use wackiness in his favor, not when he has an expensive machine that needs to be taken care of and fine-tuned.
The Valentine who has been effective in years past never really got a chance to pop out of his shell in this latest go-around, with Valentine so obviously treading carefully from his first minute with the Red Sox. Valentine has had to spend just as much energy this season making sure not to make mistakes as he had trying something new. The fatigue he is showing on the job is not just the result of a rough season, but also of tough and unique demands. It's been easy to point fingers as the season has deteriorated, but whether Valentine reacted correctly or not, this much is obvious: The buoyant skipper never had a chance to start from a clean slate.
As the Red Sox embark on their final try to swing the ship around and secure a solid stretch of play before this season ends, Valentine will be under heavy scrutiny. But, questions of where he sits with the Red Sox aside, his quest to manage should not be defined by a most unusual season in Boston.
If Valentine continues with the Red Sox, he'll have a chance with a new group to show what he can do next season. But if the team and Valentine part ways, the year that left everyone shaking their heads shouldn't be a death knell for what Valentine can do as a manager.
He's been shaking his head just as much. But he's been fighting through it — and maybe finding enough tricks that he can expand the manager resume that was already well-stocked when this adventure began.