There has been talk that both Danny Califf and Stefan Frei could be on their way out of Toronto at some point this season. Both players were expected to be starters for the club this season but they lost their starting positions due to injuries and have not been able to win them back since. Considering the amount that Toronto FC is paying both players the club cannot afford to just have them sitting on the bench. It would make sense for the team to try and get value back for both players in trades.

On Tuesday afternoon, Brotherly Game reported that Toronto was close to working out a three team deal with the Philadelphia Union and the Chicago Fire which would have seen both players wind up in Philly and netting Toronto FC some allocation and possibly a draft pick (similar to the package the Union got for Bakary Soumare). The follow is the key part of Scott Kessler's report on the deal that fell through:

Danny Califf was almost a Philadelphia Union player again, but his return to his former team was stopped before it was officially completed. Toronto FC was part of a three-way deal including the Union and the Chicago Fire that would have sent both Califf and Stefan Frei to Philadelphia and Bakary Soumare to the Windy City. Frei, Toronto's former starting goalkeeper, would have competed with current Union starter Zac MacMath for the no.1 role in net. The deal would have given Toronto at least the $75,000 in allocation money the Union received from Chicago as part of the trade that eventually was made official (that official package was a second rounder and the aforementioned allocation money in exchange for Soumare). Instead of completing the three team negotiation, the Union killed off the deal, leaving Toronto fuming, a source with knowledge of the situation said to the Brotherly Game. Union CEO and managing partner Nick Sakiewicz was the party responsible for the cancellation of a deal that was all, but signed, sealed and delivered to Major League Soccer's head quarters, per multiple sources. Califf has been in and out of talks with the Union for over a year now. After the firing of former head coach Peter Nowak, Philadelphia reached out to Califf and attempted to work out a way for him to return to the Union despite having traded him previously in 2012, according to a source who talked with the Brotherly Game last year.

The report comes from sources who talked with Brotherly Game and considering the blog's track record can be considered to be fairly reliable. It is quite likely that this deal was very nearly completed in the recent weeks, even though Toronto ended up left out in the cold by the Union at the very last minute.

If the Union did back out of the deal at the last moment it would not likely have sat well with Kevin Payne who is used to being a respected executive around the league. One would imagine that following such a move Toronto will not be too eager to deal with Sakiewicz again in the near future. That could be a problem though as it seems unlikely that other clubs are lining up to try and land the services of Califf considering his current salary and the fact that he has not impressed since early last season when he first joined Chivas USA.

Frei likely has the higher value of the two players and could draw interest from other clubs should Toronto be shopping him around. His salary would mean that Toronto would not get a lot in return for him other than a middle round draft pick or maybe some allocation money but the point of any deal involving Califf or Frei would be clearing up cap space to improve the roster during the summer.

Not many fans would miss Califf if this deal had gone through but the reaction to losing Frei would be a lot stronger. Considering that he is the longest serving member of the club, the leader in all time appearances, a captain, and undoubtedly a fan favourite around BMO Field.

This deal is dead though so now it will be a matter of whether Toronto can find another trade partner to help them open up that cap space they so badly need to make improvements this summer.