Barry Bonds last played in a major league game in 2007. Eight years later, he is now reportedly preparing to file a grievance against Major League Baseball, contending that MLB and its teams improperly colluded to prematurely drive him from the game.

As you may recall, back in 2007 Bonds hit an impressive .276/.480/.565 during his age-43 season, all while setting MLB’s all-time career home run record by hitting his 756th career HR in August. And although Bonds was projected to post a .380 wOBA for the 2008 season, he nevertheless went unsigned that off-season, effectively ending his major league career. This despite the fact that he had even gone so far as to offer to play for the league minimum salary (set at the time at $390,000 per year).

These relatively suspicious circumstances caused many to speculate that MLB’s teams conspired together to drive Bonds from the game. Indeed, both Bonds’ agent (Jeff Borris) and the Major League Baseball Players Association expressed concern at the time that MLB clubs had jointly agreed not to sign Bonds, with the MLBPA announcing after the 2008 season that it had found evidence of improper collusion. Despite all of this, however, Bonds and the union ultimately decided at the time not to officially charge MLB’s franchises with collusion, instead reaching an agreement with MLB to postpone any grievance against the league until Bonds had resolved his then-pending criminal charges relating to his alleged perjury and obstruction of justice during the federal BALCO investigation.

Fast-forward to last month, when the Ninth Circuit Court of Appeals reversed Bonds’ criminal conviction for obstruction of justice. With Bonds’ criminal troubles now all but behind him – technically, prosecutors are still considering whether to file a long-shot, last-ditch appeal to the U.S. Supreme Court – he is now once again returning his attention to potentially filing a grievance against MLB. So does Bonds has any chance of winning a case against the league, and if so, what might he stand to gain from charging its teams with collusion?

To begin, collusion of the sort that Bonds is alleging – in which two or more MLB teams jointly agree not to sign a particular player – is clearly prohibited under MLB’s collective bargaining agreement. Article XX(E) of the CBA specifically states that “Clubs shall not act in concert with other Clubs” when either deciding whether to sign a particular player, or determining how much to offer him in salary. Under the CBA, any such allegations of collusion must be resolved through arbitration, rather than litigation in court.

If an arbitrator determines that two or more teams have improperly colluded under Article XX(E), then the provision goes on state that the affected player(s) shall be awarded triple damages (i.e., three times the income they lost due to the collusion). Meanwhile, if five or more teams are found to have engaged in collusion, then the MLBPA would have the right to opt out of the existing CBA under Article XX(E)(5).

So if Bonds does choose to file a grievance, he will have to prove that two or more MLB teams reached an agreement not to sign him for the 2008 season. In contrast, MLB will argue that there was no agreement among its teams to drive Bonds out of baseball, but instead that each of its 30 teams individually decided not to offer him a contract, with each club acting independently of one another.

Notably, the MLBPA has never publicly revealed what sort of evidence it uncovered back in 2008 relating to MLB’s alleged collusion. It is possible, for instance, that the union found some sort of memorandum circulated among MLB teams explicitly stating – or, at least, implicitly suggesting – that teams should not sign Bonds to a new contract. Alternatively, the union may instead be planning to rely on more circumstantial evidence of collusion, emphasizing the mysterious circumstances surrounding Bonds’ inability to procure an offer for 2008. Indeed, one would usually expect that the reigning National League on-base percentage leader would receive at least one contract offer for the following season, especially after he publicly stated that he was willing to sign a contract for the league minimum salary.

This is the sort of evidence that helped the MLBPA win its initial collusion grievance case against MLB back in the 1980s, for example. The MLBPA alleged that MLB teams had agreed not to compete for the services of each others’ free agents following the 1985 season. The union’s allegations were not only based on the fact that only a single free agent – Carlton Fisk – had received an offer from a new team that off-season, but also on a memorandum circulated among MLB teams urging clubs to “exercise more self-discipline in making their operating decisions and to resist the temptation to give in to the unreasonable demands of experienced marginal players.” This evidence ultimately convinced an arbitrator to rule that the MLB franchises had improperly colluded in violation of the CBA. (The MLBPA would subsequently win two more grievances for similar collusion by MLB teams following the 1986 and 1987 seasons as well.)

Barring a smoking gun document clearly showing that the MLB clubs had colluded, however, it is uncertain whether circumstantial evidence alone would be enough to convince an arbitrator to rule in Bonds’ favor. Indeed, MLB will undoubtedly contend that its teams had ample reason to each independently decide not to offer Bonds a contract for the 2008 season. Not only had Bonds earned a reputation for being a difficult teammate and a suspected PED user, but he was also entering his age-44 season, and therefore presented a significant risk for a steep decline. In addition, Bonds would have been playing under a cloud of legal troubles in 2008, after being charged in November 2007 with 14 counts of perjury and obstruction of justice (a case that – at the time – was expected to go to trial in early 2009).

Moreover, as Rob Neyer pointed out last week, only a handful of teams were a logical fit for Bonds at the time. Because his defense had declined significantly by 2008, Bonds’ most natural role at that point would have been as a designated hitter. However, all but 5 or 6 American League teams already had a competent DH on their roster during the 2007-08 off-season. And while it is true that the fact that none of those 5 or 6 teams in need of an upgrade at DH were willing to sign Bonds – even at the league minimum salary – could suggest that there was some sort of collusion taking place, it is also plausible that such a relatively small number of teams did, in fact, each independently decide that signing Bonds wasn’t worth the potential headaches. So given all that, MLB can credibly argue that its teams did not engage in collusion.

Assuming that Bonds and the union were to win the grievance, though, he would then be entitled to be compensated for any salary lost due to the collusion. Along these lines, the MLBPA would likely rely on other contracts signed that off-season to try to ascertain what the market for Bonds would have been absent collusion. For instance, the union could point out that Mike Cameron signed a $7 million contract that off-season for his age-35 season, coming off a year in which he’d hit only .242/.328/.431 (in an era when Cameron’s defensive contributions weren’t valued as highly by most clubs as they are today). Similarly, Cliff Floyd received $3 million for his age-35 season in 2008 after posting a .284/.373/.422 line the year before (all while arguably being equally as defensively challenged as Bonds was at the time).

Moreover, the MLBPA could also potentially argue that absent collusion, Bonds would have normally received multi-year contract offers, elevating the amount of his potential damages. And ultimately, should Bonds prevail in the grievance, whatever amount the arbitrator determines he would have received had teams fairly competed for his services during the 2007-08 off-season will be tripled under the terms of the CBA. So a successful case could very well result in MLB being ordered to pay Bonds something in the $20 to $30 million range, if not more.

All in all, then, it is not surprising that Bonds and the union may pursue a grievance against MLB. Not only is Bonds undoubtedly still upset about his (perceived) premature, forced retirement from baseball, but a victorious grievance could potentially earn him tens of millions of dollars in damages. Ultimately, however, Bonds’ odds of winning the case will hinge on the strength of the evidence the MLBPA has collected indicating that MLB teams colluded to drive Bonds out of the game.