As is commonplace in the Chicago sports world, the Bears’ recent preseason losses to the New York Giants and the Tennessee Titans have caused sportswriters, bloggers and spectators to begin pointing fingers. Of particular interest is the working relationship, or lack thereof, between starting quarterback, Jay Cutler, and newly acquired wide receiver, seeking redemption, Roy Williams. When specifically questioned about his connection with Williams, Cutler simply stated, “We’re still working on it, we’ll see how it goes.”Bears fans are hoping and relying on the development of a strong understanding and relationship evolving between the two stars. Cutler, a Southern Indiana boy, turned southern aristocrat via Vanderbilt and Williams, and Williams, born in football country in Odessa, Texas, turned University of Texas star, have more in common than they might think.Both players found themselves in the tabloids this off-season due to failed romantic interludes: Williams to former Miss Texas, USA, Brooke Daniels, and Cutler to reality TV star Kristin Cavallari.Seemingly innocuous instances such as the comings and goings of professional athletes’ WAGs (Wives and Girlfriends) is not to be scoffed at as tabloid nonsense. Because success in professional athletics takes lifelong dedication and an unhealthy amount of singular focus, such romantic distractions may upset an athlete’s delicate routine, which many depend on for on-field success. In addition, despite earning relatively large amounts of money each year, due to the level of extravagance, many athletes cannot afford to throw away hundreds of thousands of dollars on passing relationships.While many athletes have access to top rate representation in contract negotiation, brand management and marketing; agents and managers seldom handle the athlete’s family law issues. Whether it is a 5-carat engagement ring given in contemplation of marriage, a luxury car, apartment, cosmetic dentistry or tuition payments given during courtship, athletes who give extravagant gifts often times, despite their high incomes, cannot afford to lose those gifts along with their lost loves.Cases in point: Cutler ponied up a reported $125,000 while Williams reportedly spent $76,000 on his engagement ring. Subsequently, both engagements were terminated and the question remained as to who had legal right to the engagement rings. As in all legal matters, the statute, case law and the case-specific facts are of the utmost importance.Under Illinois law, a gift requires donative intent; delivery, which is relinquishment of all control; and acceptance by the donee. However, a gift given in contemplation of marriage is deemed to be conditional on the subsequent marriage of the parties. If the marriage is broken off, the Court looks at who broke off the engagement. If the woman donee broke off the engagement or it was a mutual decision, the ring must be returned to the man donor. Interestingly, Illinois has yet to be presented with the situation where the man donor breaks off the engagement. Although Cutler reportedly broke off his engagement, he was fortunate that Cavallari voluntarily returned the ring and no lawsuits were filed.Although the law is quite clear in Illinois, athletes’ family law problems travel across the country along with them. While Illinois follows the no-fault, conditional-gift approach, Texas, where Williams’ engagement snafu occurred, utilizes a fault-based, conditional-gift rule. The change in jurisdiction would have made all the difference had Williams and Cutler reversed locations. Williams, who was rebuked by the beauty queen, would have eventually been granted his relief in either jurisdiction. Cutler, who reportedly called off the wedding, would have been without recourse and short $125,000 if he had found himself in Texas due to his unilateral decision to call off his big day.In Texas, like in Illinois, a gift given in contemplation of marriage is deemed to be conditional on the subsequent marriage of the parties. However, absent a written agreement to the contrary, if the donor is at fault in breaking off the engagement, then the donee may have the right to retain the engagement ring. Other jurisdictions that follow Texas in the fault-based, conditional-gift rule are Colorado, California and Connecticut, while Iowa, New Mexico, Wisconsin and Minnesota are more in line with Illinois. When working with clients who have personal affairs across many jurisdictions, it is important to be aware which forum is most beneficial for your client’s case under his particular set of circumstances.Cutler and Williams realize they have common experiences and bond over their near matrimonial misses and work on developing an off-field chemistry that will manifest into on-field magic.Family law, like sports, is more intricate and nuanced than the average legal practitioner may know; having expert consultants in the areas that touch an athlete’s life can sometimes be the difference between a small off-season news blip (Williams/Cutler) and a career defining family law related incident like Tiger Woods.